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+The Project Gutenberg EBook of History of Phosphorus, by Eduard Farber
+
+This eBook is for the use of anyone anywhere at no cost and with
+almost no restrictions whatsoever.  You may copy it, give it away or
+re-use it under the terms of the Project Gutenberg License included
+with this eBook or online at www.gutenberg.org
+
+
+Title: History of Phosphorus
+
+Author: Eduard Farber
+
+Release Date: September 20, 2010 [EBook #33766]
+
+Language: English
+
+Character set encoding: ISO-8859-1
+
+*** START OF THIS PROJECT GUTENBERG EBOOK HISTORY OF PHOSPHORUS ***
+
+
+
+
+Produced by Chris Curnow, Joseph Cooper, Louise Pattison
+and the Online Distributed Proofreading Team at
+https://www.pgdp.net
+
+
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+
+
+
+
+
+
+Transcriber's Note.
+
+This is Paper 40 from the Smithsonian Institution United States National
+Museum Bulletin 240, comprising Papers 34-44, which will also be
+available as a complete e-book.
+
+The front material, introduction and relevant index entries from the
+Bulletin are included in each single-paper e-book.
+
+Corrections are listed at the end of the e-book.
+
+
+
+
+SMITHSONIAN INSTITUTION
+
+UNITED STATES NATIONAL MUSEUM
+
+BULLETIN 240
+
+
+[Illustration]
+
+SMITHSONIAN PRESS
+
+
+MUSEUM OF HISTORY AND TECHNOLOGY
+
+CONTRIBUTIONS FROM THE MUSEUM OF HISTORY AND TECHNOLOGY
+
+  _Papers 34-44_
+  _On Science and Technology_
+
+SMITHSONIAN INSTITUTION . WASHINGTON, D.C. 1966
+
+
+
+
+_Publications of the United States National Museum_
+
+
+The scholarly and scientific publications of the United States National
+Museum include two series, _Proceedings of the United States National
+Museum_ and _United States National Museum Bulletin_.
+
+In these series, the Museum publishes original articles and monographs
+dealing with the collections and work of its constituent museums--The
+Museum of Natural History and the Museum of History and
+Technology--setting forth newly acquired facts in the fields of
+anthropology, biology, history, geology, and technology. Copies of each
+publication are distributed to libraries, to cultural and scientific
+organizations, and to specialists and others interested in the different
+subjects.
+
+The _Proceedings_, begun in 1878, are intended for the publication, in
+separate form, of shorter papers from the Museum of Natural History.
+These are gathered in volumes, octavo in size, with the publication date
+of each paper recorded in the table of contents of the volume.
+
+In the _Bulletin_ series, the first of which was issued in 1875, appear
+longer, separate publications consisting of monographs (occasionally in
+several parts) and volumes in which are collected works on related
+subjects. _Bulletins_ are either octavo or quarto in size, depending on
+the needs of the presentation. Since 1902 papers relating to the
+botanical collections of the Museum of Natural History have been
+published in the _Bulletin_ series under the heading _Contributions from
+the United States National Herbarium_, and since 1959, in _Bulletins_
+titled "Contributions from the Museum of History and Technology," have
+been gathered shorter papers relating to the collections and research of
+that Museum.
+
+The present collection of Contributions, Papers 34-44, comprises
+Bulletin 240. Each of these papers has been previously published in
+separate form. The year of publication is shown on the last page of each
+paper.
+
+FRANK A. TAYLOR _Director, United States National Museum_
+
+
+
+
+    CONTRIBUTIONS FROM
+    THE MUSEUM OF HISTORY AND TECHNOLOGY:
+    PAPER 40
+
+
+
+
+    HISTORY OF PHOSPHORUS
+
+    _Eduard Farber_
+
+
+
+
+          THE ELEMENT FROM ANIMALS AND PLANTS      178
+
+                                   EARLY USES      181
+
+    CHEMICAL CONSTITUTION OF PHOSPHORIC ACIDS      182
+
+                PHOSPHATES AS PLANT NUTRIENTS      185
+
+         FROM INORGANIC TO ORGANIC PHOSPHATES      187
+
+                 PHOSPHATIDES AND PHOSPHAGENS      189
+
+                    NUCLEIN AND NUCLEIC ACIDS      192
+
+           PHOSPHATES IN BIOLOGICAL PROCESSES      197
+
+                        MEDICINES AND POISONS      198
+
+
+
+
+_Eduard Farber_
+
+
+
+
+HISTORY OF PHOSPHORUS
+
+
+     _The "cold light" produced by phosphorus caused it to be
+     considered a miraculous chemical for a long time after its
+     discovery, about 1669. During the intervening three centuries
+     numerous other chemical miracles have been found, yet
+     phosphorus retains a special aura of universal importance in
+     chemistry. Many investigators have occupied themselves with
+     this element and its diverse chemical compounds. Further
+     enlightenment and insight into the ways of nature can be
+     expected from these efforts._
+
+     _Not only is the story of phosphorus a major drama in the
+     history of chemistry; it also illustrates, in a spectacular
+     example, the growth of this science through the discovery of
+     connections between apparently unrelated phenomena, and the
+     continuous interplay between basic science and the search for
+     practical usage._
+
+     THE AUTHOR: _Eduard Farber is a research professor at American
+     University, Washington, D.C., and has been associated with the
+     Smithsonian Institution as a consultant in chemistry._
+
+
+When phosphorus was discovered, nearly three centuries ago, it was
+considered a miraculous thing. The only event that provoked a similar
+emotion was the discovery of radium more than two centuries later. The
+excitement about the _Phosphorus igneus_, Boyle's _Icy Noctiluca_, was
+slowly replaced by, or converted into, chemical research. Yet, if we
+would allow room for emotion in research, we could still be excited
+about the wondrous substance that chemical and biological work continues
+to reveal as vitally important. It is a fundamental plant nutrient, an
+essential part in nerve and brain substance, a decisive factor in muscle
+action and cell growth, and also a component in fast-acting, powerful
+poisons. The importance of phosphorus was gradually recognized and the
+means by which this took place are characteristic and similar to other
+developments in the history of science. This paper was written in order
+to summarize these various means which led to the highly complex ways of
+present research.
+
+
+
+
+The Element from Animals and Plants
+
+
+It was a little late to search for the philosophers' stone in 1669, yet
+it was in such a search that phosphorus was discovered. Wilhelm Homberg
+(1652-1715) described it in the following manner: Brand, "a man little
+known, of low birth, with a bizarre and mysterious nature in all he
+did, found this luminous matter while searching for something else. He
+was a glassmaker by profession, but he had abandoned it in order to be
+free for the pursuit of the philosophical stone with which he was
+engrossed. Having put it into his mind that the secret of the
+philosophical stone consisted in the preparation of urine, this man
+worked in all kinds of manners and for a very long time without finding
+anything. Finally, in the year 1669, after a strong distillation of
+urine, he found in the recipient a luminant matter that has since been
+called phosphorus. He showed it to some of his friends, among them
+Mister Kunkel [sic]."[1]
+
+Neither the name nor the phenomenon were really new. Organic
+phosphorescent materials were known to Aristotle, and a lithophosphorus
+was the subject of a book published in 1640, based on a discovery made
+by a shoemaker, Vicenzo Casciarolo, on a mountain-side near Bologna in
+1630.[2] Was the substance new which Brand showed to his friends? Johann
+Gottfried Leonhardi quotes a book of 1689 in which the author, Kletwich,
+claims that this phosphorus had already been known to Fernelius, the
+court physician of King Henri II of France (1154-1189).[3] To the same
+period belongs the "Ordinatio Alchid Bechil Saraceni philosophi," in
+which Ferdinand Hoefer found a distillation of urine with clay and
+carbonaceous material described, and the resulting product named
+escarbuncle.[4] It would be worth looking for this source; although
+Bechil would still remain an entirely unsuccessful predecessor, it does
+seem strange that in all the distillations of arbitrary mixtures, the
+conditions should never before 1669 have been right for the formation
+and the observation of phosphorus.
+
+[Illustration: Figure 1.--THE ALCHEMIST DISCOVERS PHOSPHORUS. A painting
+by Joseph Wright (1734-1779) of Derby, England.]
+
+For Brand's contemporaries at least, the discovery was new and exciting.
+The philosopher Gottfried Wilhelm von Leibniz (1646-1716) considered it
+important enough to devote some of his time (between his work as
+librarian in Hanover and Wolfenbüttel, his efforts to reunite the
+Protestant and the Catholic churches, and his duties as Privy Councellor
+in what we would call a Department of Justice) to a history of
+phosphorus. This friend of Huygens and Boyle tried to prove that Kunckel
+was not justified in claiming the discovery for himself.[5] Since then,
+it has been shown that Johann Kunckel (1630-1703) actually worked out
+the method which neither Brand nor his friend Kraft wanted to disclose.
+Boyle also developed a method independently, published it, and
+instructed Gottfried Hankwitz in the technique. Later on, Jean Hellot
+(1685-1765) gave a meticulous description of the details and a long
+survey of the literature.[6]
+
+[Illustration: Figure 2.--GALLEY-OVEN, 1869. The picture is a cross
+section through the front of the oven showing one of the 36 retorts, the
+receivers for the distillate, and the space in the upper story used for
+evaporating the mixture of acid solution of calcium phosphate and coal.
+(According to ANSELME PAYEN, _Précis de Chimie industrielle_, Paris,
+1849; reproduced from HUGO FLECK, _Die Fabrikation chemischer Produkte
+aus thierischen Abfällen_, Vieweg, Braunschweig, 1862, page 80 of volume
+2, 2nd group, of P. BOLLEY'S _Handbuch der chemischen Technologie_.)]
+
+To obtain phosphorus, a good proportion of coal (regarded as a type of
+phlogiston) was added to urine, previously thickened by evaporation and
+preferably after putrefaction, and the mixture was heated to the highest
+attainable temperature. It was obvious that phlogiston entered into the
+composition of the distillation product. The question remained whether
+this product was generated _de novo_. In his research of 1743 to 1746,
+Andreas Sigismund Marggraf (1709-1782) provided the answer. He found the
+new substance in edible plant seeds, and he concluded that it enters the
+human system through the plant food, to be excreted later in the urine.
+He did not convince all the chemists with his reasoning. In 1789,
+Macquer wrote: "There are some who, even at this time, hold that the
+phosphorical ('phosphorische') acid generates itself in the animals and
+who consider this to be the 'animalistic acid.'"[7]
+
+Although Marggraf was more advanced in his arguments than these
+chemists, yet he was a child of his time. The luminescent and
+combustible, almost wax-like substance impressed him greatly. "My
+thoughts about the unexpected generation of light and fire out of water,
+fine earth, and phlogiston I reserve to describe at a later time." These
+thoughts went so far as to connect the new marvel with alchemical wonder
+tales. When Marggraf used the "essential salt of urine," also called
+_sal microcosmicum_, and admixed silver chloride ("horny silver") to it
+for the distillation of phosphorus, he expected "a partial conversion of
+silver by phlogiston and the added fine vitrifiable earth, but no trace
+of a more noble metal appeared."[8]
+
+Robert Boyle had already found that the burning of phosphorus produced
+an acid. He identified it by taste and by its influence on colored plant
+extracts serving as "indicators." Hankwitz[9] described methods for
+obtaining this acid, and Marggraf showed its chemical peculiarities.
+They did not necessarily establish phosphorus as a new element. To do
+that was not as important, at that time, as to conjecture on analogies
+with known substances. Underlying all its unique characteristics was the
+analogy of phosphorus with sulfur. Like sulfur, phosphorus can burn in
+two different ways, either slowly or more violently, and form two
+different acids. The analogy can, therefore, be extended to explain the
+results in both groups in the same way. In the process of burning, the
+combustible component is removed, and the acid originally combined with
+the combustible is set free. Whether the analogy should be pursued even
+further remained doubtful, although some suspicion lingered on for a
+while that phosphoric acid might actually be a modified sulfuric acid.
+Analogies and suspicions like these were needed to formulate new
+questions and stimulate new experiments. They are cited here for their
+important positive value in the historical development, and not for the
+purpose of showing how wrong these chemists were from our point of
+view, a point of view which they helped to create.
+
+The widespread interest in the burning of sulfur and of phosphorus,
+naturally, caught Lavoisier's attention. In his first volume of
+_Opuscules Physiques et Chimiques_ (1774), he devoted 20 pages to his
+experiments on phosphorus. He amplified them a few years later[10] when
+he attributed the combustion to a combination of phosphorus with the
+"eminently respirable" part of air. In the _Méthode de Nomenclature
+Chimique_ of 1787, the column of "undecomposed substances" lists sulfur
+as the "radical sulfurique," and phosphorus, correspondingly, as the
+"radical phosphorique." The acids are now shown to be compounds of the
+"undecomposed" radicals, the complete reversion of the previous concept
+of this relationship. A part of the old analogy remained as far as the
+acids are concerned: sulfuric acid corresponds to phosphoric; sulfurous
+acid to phosphorous acid with less oxygen than in the former.[11]
+
+
+
+
+Early Uses
+
+
+In the 18th century, phosphorus was a costly material. It was produced
+mostly for display and to satisfy curiosity. Guillaume François Rouelle
+(1703-1770) demonstrated the process in his lectures, and, as Macquer
+reports, he "very often" succeeded in making it.[12] Robert Boyle had
+the idea of using phosphorus as a light for underwater divers.[13] A
+century later, "instant lights" were sold, with molten phosphorus as the
+"igniter," but they proved cumbersome and unreliable.[14] Because white
+phosphorus is highly poisonous, an active development of the use in
+matches occurred only after the conversion of the white modification
+into the red had been studied by Émile Kopp (1844), by Wilhelm Hittorf
+(1824-1914) and, in its practical application, by Anton Schrötter
+(1802-1875).[15]
+
+[Illustration: Figure 3.--DISTILLATION APPARATUS (1849) for refining
+crude phosphorus. The crude phosphorus is mixed with sand under hot
+water, cooled, drained, and filled into the retort. The outlet of the
+retort, at least 6 cm. in diameter, is partially immersed in the water
+contained in the bucket. A small dish, made from lead, with an iron
+handle, receives the distilled phosphorus. (From HUGO FLECK, _Die
+Fabrikation chemischer Produkte ..._ page 90.)]
+
+The most exciting early use, however, was in medicine. It is not
+surprising that such a use was sought at that time. Any new material
+immediately became the hope of ailing mankind--and of striving
+inventors.[16] Phosphorus was prescribed, in liniments with fatty oils
+or as solution in alcohol and ether, for external and internal
+application. A certain Dr. Kramer found it efficient against epilepsy
+and melancholia (1730). A Professor Hartmann recommended it against
+cramps.[17] However, in the growing production of phosphorus for
+matches, the workers experienced the poisonous effects. In the plant of
+Black and Bell at Stratford, this was prevented by inhaling turpentine.
+Experiments on dogs were carried out to show that poisoning by
+phosphorus could be remedied through oil of turpentine.[18]
+
+[Illustration: Figure 4.--APPARATUS FOR CONVERTING WHITE PHOSPHORUS into
+the red allotropic form, 1851. Redistilled phosphorus is heated in the
+glass or porcelain vessel (g) which is surrounded by a sandbath (e) and
+a metal bath (b). Vessel (j) is filled with mercury and water; together
+with valve (k), it serves as a safety device. The alcohol lamp (l) keeps
+the tube warm against clogging by solidified vapors. Because of hydrogen
+phosphides, the operation, carried out at 260° C., had to be watched
+very carefully. (According to Arthur Albright, 1851; reproduced from
+HUGO FLECK, _Die Fabrikation chemischer Produkte ..._, page 112.)]
+
+
+
+
+Chemical Constitution of Phosphoric Acids
+
+
+In a long article on phosphorus, Edmond Willm wrote in 1876: "For a
+century, urine was the only source from which phosphorus was obtained.
+After Gahn, in 1769, recognized the presence of phosphoric acid in
+bones, Scheele indicated the procedure for making phosphorus from
+them."[19] Actually, Gahn used at first hartshorn (_Cornu cervi
+ustum_), and Scheele doubted, until he checked it himself, that his
+esteemed friend was right. A few years later, Scheele corrected Gahn's
+assumption that the _sal microcosmicum_ was an ammonia salt; instead, it
+is "a tertiary neutral salt, consisting of _alkali minerali fixo_ (i.e.,
+sodium), _alkali volatili_, and _acido phosphori_."[20]
+
+In the years after 1770, phosphorus was discovered in bones and many
+other parts of various animals. Treatment with sulfuric acid decomposed
+these materials into a solid residue and dissolved phosphoric acid. Many
+salts of this acid were produced in crystalline form. Heat resistance
+had been considered one of the outstanding characteristics of phosphoric
+acid. Now, however, in the processes of drying and heating certain
+phosphates, it became clear that three kinds of phosphoric acids could
+be produced: _ortho_, _pyro_, and _meta_.
+
+Berzelius cited these acids as examples of compounds which are ISOMERIC.
+This word was intended to designate compounds which contain the same
+number of atoms of the same elements but combined in different manners,
+thereby explaining their different chemical properties and crystal
+forms. It was in 1830 that Berzelius propounded this companion of the
+concept, ISOMORPHISM, which was to collect all cases of equal crystal
+form in compounds in which equal numbers of atoms of different elements
+are put together in the same manner. Together, the two concepts of
+isomerism and isomorphism seemed to cover all the known exceptions from
+the simplest assumption as to specificity and chemical composition.
+
+However, only a few years later Thomas Graham (1805-1869) proved that
+the three phosphoric acids are not isomeric. He used the proportion of 2
+P to 5 O in the oxide which Berzelius had thought justified at least
+until "an example of the contrary could be sufficiently
+established."[21] Refining the techniques of Gay-Lussac (1816) and
+several other investigators, Graham characterized the three phosphoric
+acids as "a terphosphate, a biphosphate, and phosphate of water."
+Actually, this was the wrong terminology for what he meant and
+formulated as trihydrate, bihydrate, and monohydrate of phosphorus
+oxide. In his manner of writing the formulas, each dot over the symbol
+for the element was to indicate an atom of oxygen; thus, he wrote:
+
+    ...   :: ..   ...    . .
+    H^{3} P  H^{2} P and H P.[22]
+
+[Illustration: Figure 5.--OVEN FOR THE CALCINATION OF BONES, about 1870.
+"The operation is carried out in a rather high oven, such as shown....
+The fresh bones are thrown in at the top of the oven, B. First, fuel in
+chamber F is lighted, and a certain quantity of bones is burnt on the
+grid D. When these bones are burning well, the oven is gradually filled
+with bones, and the combustion maintains itself without addition of
+other fuel. A circular gallery, C, surrounds the bottom of the oven and
+carries the products of combustion into the chimney, H. The calcined
+bones are taken out at the lower opening, G, by removing the bars of
+grid B." (Translation of the description from FIGUIER, _Merveilles de
+l'industrie_, volume 3, 1874, page 537.)]
+
+[Illustration: Figure 6.--AN ADVERTISEMENT with view of plant for
+manufacturing superphosphate about 1867. (From E. T. FREEDLEY,
+_Philadelphia and its Manufacturers in 1867_, page 288.)]
+
+Graham had come to this understanding of the phosphoric acids through
+his previous studies of "Alcoates, definite compounds of Salts and
+Alcohol analogous to the Hydrates" (1831). Liebig started from analogies
+he saw with certain organic acids when he formulated the phosphoric
+acids with a constant proportion of water (aq.) and varying proportions
+of "phosphoric acid" (P) as follows:
+
+    2 P 3 aq.  phosphoric acid
+    3 P 3 aq.  pyrophosphoric acid
+    6 P 3 aq.  metaphosphoric acid.
+
+[Illustration: Figure 7.--FLORIDA HARD-ROCK PHOSPHATE MINING. (From
+Carroll D. Wright, _The Phosphate Industry of the United States_, sixth
+special report of the Commissioner of Labor, Government Printing Office,
+Washington, 1893, plate facing page 43.)]
+
+Salts are formed when a "basis," i.e., a metal oxide, replaces water.
+When potassium-acid sulfate is neutralized by sodium base, the acid-salt
+divides into Glauber's salt and potassium sulfate, which proves the
+acid-salt to be a mixture of the neutral salt with its acid. Sodium-acid
+phosphate behaves quite differently. After neutralization by a potassium
+"base" (hydroxide), the salt does not split up; a uniform
+sodium-potassium phosphate is obtained. Therefore, phosphoric acid is
+truly three-basic![23]
+
+This result has later been confirmed, but the analogy by means of which
+it had been obtained was very weak, in certain parts quite wrong.
+
+The acids from the two lower oxides of phosphorus were also considered
+as three-basic. Adolphe Wurtz (1817-1884) formulated them in 1846,
+according to the theory of chemical types:
+
+    (PO)···
+            O^{3}  phosphoric acid
+      H^{3}
+
+    (PHO)··
+            O^{2}  phosphorus acid
+       H^{2}
+
+    (PH^{2}O)·
+               O   hypophosphorous acid.[24]
+           H
+
+Further proof for these constitutions was sought in the study of the
+esters formed when the acids react with alcohols.
+
+Among the analogies and generalizations by which the research on
+phosphoric acid was supported, and to the results of which it
+contributed a full share, was the new theory of acids. Not oxygen,
+Lavoisier's general acidifier, but reactive hydrogen determines the
+character of acids. In this brief survey, it seems sufficient just to
+mention this connection without describing it in detail.
+
+The study of phosphoric acids led to important new concepts in
+theoretical chemistry. The finding of polybasicity was extended to other
+acids and formed the model that helped to recognize the
+polyfunctionality in other compounds, like alcohols and amines. The
+hydrogen theory of acids was fundamental for further advance. In another
+dimension, it is particularly interesting to see that large-scale
+applications followed almost immediately and directly from the new
+theoretical insight. The first and foremost of these applications was in
+agriculture.
+
+
+
+
+Phosphates as Plant Nutrients
+
+
+One hundred years after the discovery of "cold light," the presence of
+phosphorus in plants and animals was ascertained, and its form was
+established as a compound of phosphoric acid. This knowledge had little
+practical effect until the "nature" of the acid, in its various forms,
+was explained through the work of Thomas Graham. From it, there started
+a considerable technical development.
+
+At about that time (1833), the Duke of Richmond proved that the
+fertilizing value of bones resided not in the gelatin, nor in the
+calcium, but in the phosphoric acid. Thus, he confirmed what Théodore de
+Saussure had said in 1804, that "we have no reason to believe" that
+plants can exist without phosphorus. Unknowingly at first, the farmer
+had supplied this element by means of the organic fertilizers he used:
+manure, excrements, bones, and horns. Now, with the value of phosphorus
+known, a search began for mineral phosphates to be applied as
+fertilizers. Jean Baptiste Boussingault (1802-1887), an agricultural
+chemist in Lyons, traveled to Peru to see the guano deposits. Garcilaso
+de la Vega (ca. 1540 to ca. 1616) noted in his history of Peru (1604)
+that guano was used by the Incas as a fertilizer. Two hundred years
+later, Alexander von Humboldt revived this knowledge, and Humphry Davy
+wrote about the benefits of guano to the soil. Yet, the application of
+this fertilizer developed only slowly, until Justus Liebig sang its
+praise. Imports into England rose and far exceeded those into France
+where, between 1857 and 1867, about 50,000 tons were annually received.
+
+The other great advance in the use of phosphatic plant nutrients started
+with Liebig's recommendation (1840) to treat bones with sulfuric acid
+for solubilization. This idea was not entirely new; since 1832, a
+production of a "superphosphate" from bones and sulfuric acid had been
+in progress at Prague. At Rothamsted in 1842, John Bennet Lawes
+obtained a patent on the manufacture of superphosphate. Other
+manufactures in England followed and were successful, although James
+Muspratt (1793-1886) at Newton lost much time and "some thousands of
+pounds" on Liebig's idea of a "mineral manure."
+
+[Illustration: Figure 8.--FLORIDA LAND-PEBBLE PHOSPHATE MINING. (From
+Carroll D. Wright, _The Phosphate Industry of the United States ..._,
+plate facing page 58.)]
+
+It was difficult enough to establish the efficacy of bones and
+artificially produced phosphates in promoting the growth of plants under
+special conditions of soils and climate; therefore, the question as to
+the action of phosphates in the growing plant was not even seriously
+formulated at that time. The beneficial effects were obvious enough to
+increase the use of phosphates as plant nutrients and to call for new
+sources of supply. Active developments of phosphate mining and treating
+started in South Carolina in 1867, and in Florida in 1888.[25]
+
+In a reciprocal action, more phosphate application to soils stimulated
+increasing research on the conditions and reactions obtaining in the
+complex and varying compositions called soil. The findings of
+bacteriologists made it clear that physics and chemistry had to be
+amplified by biology for a real understanding of fertilizer effects.
+After 1900, for example, Julius Stoklasa (1857-1936) pointed out that
+bacterial action in soil solubilizes water-insoluble phosphates and
+makes them available to the plants.[26]
+
+[Illustration: Figure 9.--FLORIDA RIVER-PEBBLE PHOSPHATE MINING. (From
+Carroll D. Wright, _The Phosphate Industry of the United States ..._,
+plate facing page 64.)]
+
+The insight into the importance of phosphorus in organisms, especially
+since Liebig's time, is reflected in the work of Friedrich Nietzsche
+(1844-1900). This "re-valuator of all values" who modestly said of
+himself: "I am dynamite!" once explained the human temperaments as
+caused by the inorganic salts they contain: "The differences in
+temperament are perhaps caused more by the different distribution and
+quantities of the inorganic salts than by everything else. Bilious
+people have too little sodium sulfate, the melancholics are lacking in
+potassium sulfate and phosphate; too little calcium phosphate in the
+phlegmatics. Courageous natures have an excess of iron phosphate." (See
+volume 12 of _Nietzsche's Works_, edit. Naumann-Kröner, Leipzig, 1886.)
+In this strange association of inorganic salts with human temperaments,
+the role of iron phosphate as a producer of courage is particularly
+interesting. What would a modern philosopher conclude if he followed the
+development of insight into the composition and function of complex
+phosphate compounds in organisms?
+
+
+
+
+From Inorganic to Organic Phosphates
+
+
+By the middle of the 19th century, the source of phosphorus in natural
+phosphates and the chemistry of its oxidation products had been
+established. The main difficulty that had to be overcome was that these
+oxidation products existed in so many forms, not only several stages of
+oxidation, but, in addition, aggregations and condensations of the
+phosphoric acids. Once the fundamental chemistry of these acids was
+elucidated, the attention of chemists and physiologists turned to the
+task of finding the actual state in which phosphorus compounds were
+present in the organisms. It had been a great advance when it had been
+shown that plants need phosphates in their soil. This led to the next
+question concerning the materials in the body of the plant for which
+phosphates were being used and into which they were incorporated.
+Similarly, the knowledge that animals attain their phosphates from the
+digested plant food called, in the next step of scientific inquiry, for
+information on the nature of phosphates produced from this source.
+
+The method used in this inquiry was to subject anatomically separated
+parts of the organisms to chemical separations. The means for such
+separations had to be more gentle than the strong heat and destructive
+chemicals that had been considered adequate up to then. The
+interpretation of the new results naturally relied on the general
+advance of chemistry, the development of new methods for isolating
+substances of little stability, of new concepts concerning the
+arrangements of atoms in the molecules, and of new apparatus to measure
+their rates of change.
+
+In the system of chemistry, as it developed in the first half of the
+19th century, the new development can be characterized as the turn from
+inorganic to organic phosphates, from the substance of minerals and
+strong chemical interactions to the components in which phosphate groups
+remained combined with carbon-containing substances.
+
+[Illustration: Figure 10.--ELECTRIC FURNACE FOR PRODUCING ELEMENTAL
+PHOSPHORUS, invented by Thomas Parker of Newbridge, England, and
+assigned to The Electric Construction Corporation of the same place. The
+drawing is part of United States patent 482,586 (September 13, 1892).
+The furnace was patented in England on October 29, 1889 (no. 17,060); in
+France on June 23, 1890 (no. 206,566); in Germany on June 17, 1890 (no.
+55,700); and in Italy on October 23, 1890 (no. 431). The following
+explanation is cited from the U.S. patent:
+
+Figure 1 [shown here] is a vertical section of the furnace, and Fig. 2
+is a diagram to illustrate the means for regulating the electro-motive
+force or quantity of current across the furnace.
+
+F is the furnace containing the charge to be treated. It has an
+inlet-hopper at _a_, with slides AA, by which the charge can be admitted
+without opening communication between the interior of the furnace and
+the outer air.
+
+B is a screw conveyer by which the charge is pushed forward into the
+furnace.
+
+_c´c´_ are the electrodes, consisting of blocks or cylinders or the like
+of carbon fixed in metal socket-pieces _c c_, to which the
+electric-circuit wires _d_ from the dynamo D are affixed. The current,
+as aforesaid, may be either continuous or alternating. _c^{2}c^{2}_ are
+rods of metal or carbon, which are used to establish the electric
+circuit through the furnace, the said rods being inserted into holes in
+conductors _c^{3}_ (in contact with the socket-pieces _c_) and in the
+furnace, as shown.
+
+_g_ is the outlet for the gas or vapor, _h_ the slag-tap hole, and _x_
+the opening for manipulating the charge, the said openings being closed
+by clay or otherwise when the furnace is at work.
+
+I use coke or other form of carbon in the charge between the electrodes
+_c´_, the said coke being in contact with the said electrodes, so that
+complete incandescence is insured.
+
+A means for varying the electro-motive force or quantity of current
+across the furnace with the varying resistance of the charge is
+illustrated by the diagram, Fig. 2. _c´ c^{2}_ indicate the electrodes
+in the furnace, as in Fig. 1, and D is the dynamo and T its terminals. E
+represents the exciting-circuit. R R are resistances, and R S is the
+resistance-switch, which is operated to put in more or less resistance
+at R as the resistance of the charge in the furnace lessens or
+increases. This switch may be automatically operated, and a suitable
+arrangement for the purpose is a current-regulator such as is described
+in the specification of English Letters Patent No. 14,504, of September
+14, 1889, granted to William Henry Douglas and Thomas Hugh Parker.]
+
+[Illustration:
+
+  T. PARKER.
+  ELECTRICAL FURNACE.
+
+  Patented Sept. 13, 1892.
+
+  FIG. 1.]
+
+[Illustration: FIG. 2.
+
+  _Inventor
+  Thomas Parker_
+
+  _By his attorneys
+  Howson and Howson_
+
+  _Witnesses:
+  George Baumann
+  John Revell_]
+
+[Illustration: Figure 11.--DIPPING OF MATCHSTICKS in France, about 1870.
+The frame which holds the matches so that one end protrudes at the
+bottom, is lowered over a pan containing molten sulfur. The
+sulfur-covered matches are then dropped into a phosphorous paste. See
+figure 12. (From FIGUIER, _Merveilles de l'industrie_, volume 3, 1874,
+page 575.)]
+
+
+
+
+Phosphatides and Phosphagens
+
+
+The important phosphorus compounds in organisms are much more complex
+than the simple salts, to which Nietzsche attributed such influence on
+man's character. Long before he wrote, it was known that phosphoric acid
+combines not only with inorganic bases to form salts, but with alcohols
+to form esters. In the middle of the 19th century, Théophile Juste
+Pelouze (1807-1867) extended this knowledge to an ester of glycerol.
+This proved to be significant in several respects. Glycerol had been
+shown by Michel Chevreul (1786-1889) as the substance in fats that is
+released in the process of soap boiling, when the fatty acids are
+converted into their salts. That it has the nature of an alcohol had
+been demonstrated by Marcellin Berthelot. Instead of one "alcoholic"
+hydroxyl group, OH, like ethanol (the alcohol of fermentation), or two
+hydroxyl groups (like ethylene glycol), glycerol contains three such
+groups. It was the only "natural" alcohol known at that time. That this
+alcohol would combine with phosphoric acid could be predicted, but that
+the ester, as obtained by Pelouze, still contained free acidic functions
+and formed a water-soluble barium salt was a new experience.
+
+[Illustration: Figure 12.--PAN FOR DIPPING MATCHSTICKS into phosphorus
+paste, about 1870. The letters on the picture are: A, matches; B, water
+bath; C, frame; D, plate; E, phosphorus paste; F, oven. The phosphorus
+paste of Böttger, 1842, contained 10 phosphorus, 25 antimony sulfide,
+12.5 manganese dioxide, 15 gelatin. According to Figuier (page 579), R.
+Wagner substituted lead dioxide for the manganese dioxide. (From
+FIGUIER, volume 3, 1874, page 576.)]
+
+
+ALCOHOLIC FERMENTATION
+
+  (C_{6}H_{10}O_{5})_{_n_}   C_{6}H_{12}O_{6}      C_{6}H_{12}O_{6}
+      glycogen                  glucose                 fructose
+         ^|                        ^|                      ^|
+         || H_{3}PO_{4}            || <-- ATP              || <--ATP
+         |v                        |v                      |v
+      ---------------+          ------+
+   H--C--OPO_{3}H_{2}|       H--C--OH |              H _{2}C--OH
+      |              |          |     |                    |
+   H--C--OH          |       H--C--OH |                    C--(OH)--+
+      |              |          |     |                    |        |
+  HO--C--H           O <==> HO--C--H  O   <=======>    HO--C--H     |
+      |              |          |     |                    |        O
+   H--C--OH          |       H--C--OH |                 H--C--OH    |
+      |              |          |     |                    |        |
+   H--C--------------+       H--C-----+                 H--C--------+
+      |                         |                          |
+      CH_{2}OH             H_{2}C--OPO_{3}H_{2}+ADP   H_{2}C--OPO_{3}H_{2}+ADP
+
+  glucose-1-phosphate        glucose-6-phosphate        fructose-6-phosphate
+  (Cori-ester)               (Robison-ester)            (Neuberg-ester)
+                                                          ^   |
+                                                          |   | <-- ATP
+                                                     +----|   |
+                                                     | +------|
+                                                     | |
+                                                     | v
+                                             H_{2}C--OPO_{3}H_{2}
+                                                  |
+                                                  C(OH)--+
+                                                  |      |
+                                              HO--C--H   |
+                 fructose-1,6-diphosphate         |      O
+                  (Harden-Young-ester)         H--C--OH  |
+                                                  |      |
+                                               H--C------+
+                                                  |
+                                             H_{2}C--OPO_{3}H_{2} + ADP
+                                                  ^|
+                                                  ||  O
+                                                  || //
+                             CH_{2}OPO_{3}H_{2}   || CH
+                             |                    |v |  3-phosphoglycer-aldehyde
+  dihydroxyacetone-phosphate C=O   <=============>   CHOH  (Fischer-ester)
+                             |                       |
+                             CH_{2}OH                CH_{2}OPO_{3}H_{2}
+                                                    ||  + coenzyme + H_{3}PO_{4}
+                                                  O=C--OPO_{3}H_{2}
+                                                    |
+          1,3-diphosphoglyceric acid                CHOH + dihydro-coenzyme
+           (Negelein-ester)                         |
+                                                    CH_{2}OPO_{3}H
+                                                   ^|
+                                           ADP --> ||
+                                                   || O
+                                                   |v//
+                                                    C--OH
+                                                    |      +---+
+             3-phosphoglyceric acid                 CHOH + |ATP|
+               (Nilsson-ester)                      |      +---+
+                                                    CH_{2}OPO_{3}H_{2}
+                                                   ^|
+                                                   |v
+                                                    COOH
+             2-phosphoglyceric acid                 |
+                                                    CHOPO_{3}H_{2}
+                                                    |
+                                                    CH_{2}OH
+                                                   ^|
+                                                   |v
+                                                    COOH
+                                                    |
+                 phosphopyruvic acid                COPO_{3}H_{2}
+                  (enol-)                          ||
+                                                    CH_2
+                                           ADP --> ||
+                                                    COOH
+                  +------+                          |     +---+
+                  |CO_{2}| + CH_3CHO    <--------   C=O + |ATP|
+                  +------+   acetaldehyde           |     +---+
+                  carbon    |                       CH_{3}
+                  dioxide   | + dihydro-coenzyme  pyruvic acid
+                            |
+                            v
+                     +----------------+
+                     | CH_{3}CH_{2}OH | + coenzyme
+                     +----------------+
+                      ethyl alcohol
+
+[Illustration: Figure 13.--SURVEY OF ALCOHOLIC FERMENTATION, 1951. The
+"well-known scheme of alcoholic fermentation" according to Albert Jan
+Kluyver (1888-1956), presented before the Society of Chemical Industry
+in the Royal Institution, March 7, 1951. In _Chemistry & Industry_,
+1952, page 136 ff., Kluyver restates that "... the fermentation of one
+molecule of glucose is indissolubly connected with the formation of two
+molecules of adenosine triphosphate (ATP) out of two molecules of
+adenosine diphosphate (ADP)."]
+
+Shortly after this experience had been gained, it became valuable for
+understanding the chemical nature of a new substance extracted from a
+natural organ. This substance was named lecithin by its discoverer,
+Nicolas Théodore Gobley[27] (1811-1876), because he obtained it from egg
+yolk (in Greek, _lékidos_). He used ether and alcohol for this
+extraction. Had he used water and mineral acid instead, he would not
+have found lecithin, but only its components. As Gobley and, slightly
+later, Oscar Liebreich (1839-1908), subjected lecithin to treatment with
+boiling water and acid, they separated it into three parts. One of them
+was the glycerophosphoric acid of Pelouze, the second was the well-known
+stearic acid of Chevreul, but the third was somewhat mysterious. This
+third substance was the same as one previously noticed when nerves had
+been subjected to an extraction by boiling water and acid and,
+therefore, called nerve-substance or neurine. Adolf Friedrich Strecker
+(1822-1871) established the identity of this neurine with a product he
+had extracted from bile and which went under the name of choline.
+Adolphe Wurtz (1817-1884) succeeded in synthesizing this substance from
+ethylene oxide, CH_2.O.CH_2 and trimethylamine N(CH_3)_3.[28] Thus, all
+three parts were identified, and Strecker put them together to construct
+a chemical formula for lecithin, glycerophosphoric acid combined with a
+fatty acid and with choline (a hydrate of neurine).
+
+                        { OH       }
+                      N { (CH_3)_3 } Choline
+                        { C_2H_4O  }
+
+
+    C_18H_33O_2 }               HO }
+                }                  } PO
+    C_16H_31O_2 }          C_3H_5O }
+
+    Fatty Acids        Glycerophosphate
+          \--------v-------/
+               Lecithin
+          according to Strecker
+
+This formula was not quite correct. Richard Willstätter showed that an
+internal neutralization takes place between the amino group and the free
+acidic residue. This is expressed in his lecithin formula of 1918.
+
+    CH_{2}·O·R
+    |
+    CH_{2}·O·R_2
+    |
+    |           O·CH_{2}·CH_{2}
+    |          /          \
+    CH_{2}·O--P=O         N(CH_{3})_{3}
+               \          /
+                \---O----/
+
+[Illustration: Lecithin (1918)]
+
+When the aim was to distill elementary phosphorus out of an organic
+material, it did not matter whether this was fresh or putrified. For
+obtaining lecithin out of egg yolk and similar materials, it was
+essential to use it in fresh condition. Otherwise, enzymes would have
+decomposed it. Through more recent work, four enzymes have been
+separated, which act specifically in decomposing lecithin. Enzyme A
+removes one fatty acid and leaves a complex residue, called
+lysolecithin, intact. Enzyme B attacks this residue and splits off the
+remaining fatty acid group from it, enzyme C liberates only the choline
+from lecithin, and enzyme D opens lecithin at the ester bond between
+glycerol and phosphoric acid. This is shown in the following diagram.
+
+    ENZYMATIC SPLITTING OF LECITHINS
+
+    ENZYME SUBSTRATE     PRODUCTS
+
+    A      Lecithin      Lysolecithin and fatty
+                           acids.
+
+    B      Lysolecithin  Glycero-phospho-choline
+                           and fatty acids.
+
+    C      Lecithin      Phosphatidic acid and
+                           choline.
+
+    D      Lecithin      Phosphoryl choline and
+                           diglyceride.
+
+Several fatty acids can be present in lecithin from various sources:
+palmitic and oleic acid, besides the stearic acid which at first had
+been thought the only one involved. In another group of extracts from
+brain or nerve tissue, amino-ethanol H_{2}NCH_{2}CH_{2}OH is found
+instead of the choline of lecithin. The variations include the alcohol,
+to which the fatty acids and choline phosphate are attached, for
+example, glycerol can be replaced by the so-called meat-sugar, inositol,
+which has six hydroxyl groups in its hexagon-shaped molecule
+C_{6}H_{6}(OH)_{6}.
+
+[Illustration: Figure 14.--EDUARD BUCHNER (1860-1917) received the Nobel
+Prize in Chemistry for his discovery of cell-free fermentation, the
+first step in finding the role of phosphate in fermentations (1907).]
+
+The generally similar behavior of these phosphate-and fat-containing
+substances was emphasized by Ludwig Thudichum (1829-1901). He coined the
+name phosphatides for this group of substances from seeds and
+nerves.[29] His work on the phosphates in brain substance aroused
+particular interest. When William Crookes drew his highly imaginative
+picture of an "evolution" of the chemical elements, he put into it
+"phosphorus for the brain, salt for the sea, clay for the solid
+earth...."[30] But phosphatides occur in many places of organisms, in
+bacteria, in leaves and roots of plants, in fat and tissues of animals.
+And where phosphatides are found, there are also enzymes that
+specifically act on them. They are called phosphatases to imply that
+they split the phosphatides. In addition, enzymes are present, which
+transfer phosphate groups from one compound to another. They are more
+abundant in seeds of high fat content than in the more starch-containing
+seeds, but even potatoes and orange juice have phosphatases.[31]
+
+Thus, from phosphatides, phosphoric acid is generated, and they could
+also be called phosphagens. Since 1926, however, the name phosphagens
+has been reserved for a group of organic substances that release their
+phosphoric acid very readily. The link between phosphorus and carbon is
+provided by oxygen in the phosphatides, by nitrogen in the phosphagens.
+In vertebrates, the basis for the phosphoric acid is creatine, whereas
+invertebrates have arginine instead.
+
+      H    OH                   OH
+      |   /                    /
+      N--P=O              NH--P=O
+     /    \              /     \
+    C=NH   OH           C=NH    OH
+     \                   \
+      N--CH_{2}COOH       NH
+      |                   |
+      CH_{3}              CH_{2}
+                          |
+    Creatine phosphate    CH_{2}
+                          |
+                          CH_{2}
+                          |
+                          CHNH_{2}
+                          |
+                          COOH
+
+                       Arginine phosphate
+
+
+
+
+Nuclein and Nucleic Acids
+
+
+All parts of an organism are essential for life. Only with this in mind
+does it make sense to say that the most important part of the cell is
+its nucleus. From the nuclei of cells in pus and in salmon sperm, Johann
+Friedrich Miescher (1811-1887) obtained a peculiar kind of substance,
+which he named nuclein (1868). Its phosphate content was easily
+discovered, but to find the exact proportions and the nature of the
+other components required special methods of separation from
+phosphatides and other proteins. It was difficult to develop such
+methods at a time when little was known about the properties, and
+particularly the stability, of a nuclein. For preparing nuclein from
+yeast cells, Felix Hoppe-Seyler (1825-1895) described the following
+details: Yeast is dispersed in water to extract soluble materials, like
+salts or sugars. After a few hours, the insoluble material is separated,
+washed once more with water, and then extracted with a very dilute
+solution of sodium hydroxide. The slightly alkaline solution, freed from
+insoluble residues, is slowly added to a weak hydrochloric acid. A
+precipitate forms which is separated by filtration, washed with dilute
+acid, then with cold alcohol, and finally extracted by boiling alcohol.
+The dried residue is the nuclein.[32] It contains six percent
+phosphorus. A little more washing with water, a slightly longer
+treatment with acid or alcohol gives products of lower phosphorus
+content. Many experimental variations were necessary to establish the
+procedure that leads to purification without alteration of the natural
+substance.
+
+This was also true for the methods of chemical degradation, carried out
+in order to find the components of nucleins in their highest state of
+natural complexity. It was learned for example, that the special kind of
+carbohydrate present in nucleins was very susceptible to change under
+the conditions of hydrolysis by acids. Phoebus Aaron Theodor Levine
+(1869-1940), therefore, used the digestion by a living organism. With E.
+S. London, he introduced a solution of nucleic acid into, e.g., the
+gastrointestinal segment of a dog through a gastric fistula and withdrew
+the product of digestion through an intestinal fistula. Fortunately, the
+products obtained in such degradations were not new in themselves. The
+carbohydrate in this nucleic acid proved to be identical with D-ribose,
+which Emil Fischer had artificially made from arabinose and named ribose
+to indicate this relationship (1891). The nitrogenous products of the
+degradation were identical with substances previously prepared in the
+long study of uric acid. In the course of this study, Emil Fischer
+established uric acid and a number of its derivatives as having the
+elementary skeleton of what he called "pure uric acid," abbreviated to
+purine. Out of Adolf Baeyer's work on barbituric acid came the knowledge
+of pyrimidine and its derivatives.
+
+[Illustration: Figure 15.--ALBRECHT KOSSEL (1853-1927) received the
+Nobel Prize in Medicine and Physiology in 1910 for his work on nucleic
+substances, which contain a high proportion of phosphorus. The chemical
+bonds of this phosphorus in the molecules of nucleic substances were
+determined in later work. (_Photo courtesy National Library of Medicine,
+Washington, D.C._)]
+
+From these findings, together with what Oswald Schmiedeberg (1838-1921)
+had established concerning the presence of four phosphate groups in the
+molecule (1899), Robert Feulgen (1884-1955) constructed the following
+scheme of a nucleic acid. Feulgen's formula of 1918 is:
+
+    Phosphoric acid--Carbohydrate--Guanine
+    Phosphoric acid--Carbohydrate--Cytosine
+    Phosphoric acid--Carbohydrate--Thymine
+    Phosphoric acid--Carbohydrate--Adenine
+
+Of the four basic components on the right, thymine occurs in the nucleic
+acid from the thymus gland. Yeast contains uracil instead. The
+difference between these two bases is one methyl group: thymine is a
+5-methyluracil. In all of these basic substances, the structure of urea
+
+      NH_{2}
+     /
+    C=O
+     \
+      NH_{2}
+
+is involved, and they form pairs of oxidized and reduced states:
+
+         PURINE              PYRIMIDINE
+
+     (reduced) Adenine + (oxidized) Thymine
+    (oxidized) Guanine + (reduced)  Cytosine
+
+       3N = CH4
+        |   |
+    2H--C   CH5
+        ||  ||
+        1N--CH6
+
+    Pyrimidine
+
+       1N==CH6
+        |  |    H
+        |  |  7/          N==C--NH_{2}
+    2H--C  C--N           |  |
+        || ||5 \       H--C  C--NH
+        || ||   \         || ||  \
+        || ||    CH8      || ||   CH
+        || ||   //        || ||  //
+        3N--C--N          N--C--N
+            4  9
+                         Adenine
+         Purine
+
+           HN--C=O
+            |  |
+    NH_{2}--C  C--NH       N==C--NH_{2}  H--N--C=O
+            || ||  \       |  |             |  |
+            || ||   CH   O=C  C--H        O=C  CH
+            || ||  //      |  ||            |  ||
+            N--C--N     H--N--CH           HN--CH
+
+         Guanine         Cytosine         Uracil
+
+  The carbohydrate is ribose or deoxyribose.
+
+        CHO            CHO
+        |              |
+     H--C--OH      HO--C--H
+        |              |
+    HO--C--H       HO--C--H
+        |              |
+    HO--C--H       HO--C--H
+        |              |
+        CH_{2}OH       CH_{2}OH
+
+    Arabinose      L-Ribose
+
+       Fischer and Piloty, 1891
+
+     H
+      \(1)/-----O-----\(4) (5)
+        C              CH--CH_{2}OH
+      /   \(2)     (3)/
+    HO     CH_{2}--HC(OH)
+
+            Deoxyribose
+
+The exact position of phosphoric acid was established after long work
+and verified by synthesis.[33]
+
+A compound of adenine, ribose, and phosphoric acid was found in yeast,
+blood, and in skeletal muscle of mammals. From 100 grams of such muscle,
+0.35-0.40 grams of this compound were isolated. If the muscle is at
+rest, the compound contains three molecules of phosphoric acid, linked
+through oxygen atoms. It was named adenosine triphosphate or
+adenyltriphosphoric acid,[34] usually abbreviated by the symbol ATP. It
+releases one phosphoric acid group very easily and goes over in the
+diphosphate, ADP, but it can also lose 2 P-groups as pyrophosphoric acid
+and leave the monophosphate, AMP.
+
+     N==C--NH_{2}
+     |  |
+    HC  C--N     +----O----+
+     || ||  \\   |         |
+     || ||   CH  |  OH  OH |  H       OH
+     || ||  /    |  |   |  |  |      /
+     N--C--N-----C--C---C--C--C--O--P=O
+                 |  |   |  |  |      \
+                 H  H   H  H  H       OH
+    \---------/\---------------/\--------/
+      Adenine      D-Ribose      Phosphoric
+                                   acid
+
+This change of ATP was considered to be the main source of energy in
+muscle contraction by Otto Meyerhof.[35] The corresponding derivatives
+of guanine, cytosine, and uracil were also found, and they are active in
+the temporary transfer of phosphoric acid groups in biological
+processes.
+
+Thus, the study of organic phosphates progressed from the comparatively
+simple esters connected with fatty substances of organisms to the
+proteins and the nuclear substances of the cell. The proportional amount
+of phosphorus in the former was larger than in the latter; the actual
+importance and function in the life of organisms, however, is not
+measured by the quantity but determined by the special nature of the
+compounds.
+
+[Illustration: Figure 16.--OTTO MEYERHOF (1884-1951) received one-half
+of the Nobel Prize in Medicine and Physiology in 1922 for his discovery
+of the metabolism of lactic acid in muscle, which involves the action of
+phosphates, especially adenosine duophosphates. (_Photo courtesy
+National Library of Medicine, Washington, D.C._)]
+
+[Illustration: Figure 17.--ARTHUR HARDEN (1865-1940), left, AND HANS A.
+S. VON EULER-CHELPIN (b. 1875), right, shared the Nobel Prize in
+Chemistry in 1929. Harden received it for his research in fermentation,
+which showed the influence of phosphate, particularly the formation of a
+hexose diphosphate. Euler-Chelpin received his award for his research in
+fermentation. He found coenzyme A which is a nucleotide containing
+phosphoric acid.]
+
+[Illustration: Figure 18.--GEORGE DE HEVESY (b. 1885) received the Nobel
+Prize in Chemistry in 1943 for his research with isotopic tracer
+elements, particularly radiophosphorus of weight 32 (ordinary phosphorus
+is 31).]
+
+[Illustration: Figure 19.--CARL F. CORI (b. 1896) AND HIS WIFE, GERTY T.
+CORI (1896-1957) received part of the Nobel Prize in Medicine and
+Physiology in 1947 for their study on glycogen conversion. In the course
+of this study, they identified glucose 1-phosphate, now usually referred
+to as "Cori ester," and its function in the glycogen cycle. (_Photo
+courtesy National Library of Medicine, Washington, D.C._)]
+
+The study of this function is the newest phase in the history of
+phosphorus and represents the culmination of the previous efforts. This
+newest phase developed out of an accidental discovery concerning one of
+the oldest organic-chemical industries, the production of alcohol by the
+fermentative action of yeast on sugar. A transition of carbohydrates
+through phosphate compounds to the end products of the fermentation
+process was found, and it gradually proved to be a kind of model for a
+host of biological processes.
+
+Specific phosphates were thus found to be indispensable for life. In
+reverse, the wrong kind of phosphates can destroy life. As a result, an
+important part of the new phase in phosphorus history consisted in the
+study--and use--of antibiotic phosphorus compounds.
+
+
+
+
+Phosphates in Biological Processes
+
+
+The first indication that phosphorus is important for life came from the
+experience that plants take it up from the substances in the soil. They
+incorporate it in their body substance. What makes phosphorus so
+important that they cannot grow without it? The next insight was that
+animals acquire it from their plant food. It is then found in bones, in
+fat and nerve tissue, in all cells and particularly in the cell nuclei.
+What are its functions there?
+
+The answers to such questions were developed from the study of a
+long-known process, the conversion of carbohydrates into carbon dioxide
+and alcohol by yeast. It started with Eduard Buchner's discovery of
+1890, that fermentation is produced by a preparation from yeast in which
+all living cells have been removed. When yeast is dead-ground and
+pressed out, the juice still has the ability to produce fermentation.
+
+It is strange, but in many ways characteristic for the process of
+science, that the "riddle" of phosphorus in life was solved by first
+eliminating life. In such "lifeless" fermentations, Arthur Harden found
+that the conversion of sugar begins with the formation of a hexose
+phosphate (1904). The "ferment" of yeast, called zymase, proved to be a
+composite of several enzymes. Hans von Euler-Chelpin isolated one part
+of zymase, which remains active even after heating its solution to the
+boiling point. From 1 kilogram of yeast, he obtained 20 milligrams of
+this heat-stable enzyme, which he called cozymase and identified as a
+nucleotide composed of a purine, a sugar, and phosphoric acid.[36] In
+the years between the two World Wars, zymase was further resolved into
+more enzymes, one of them the coenzyme I, which was shown to be ADP
+connected with another molecule of ribose attached to the amide of
+nicotinic acid, or diphosphopyridine nucleotide:
+
+       ^                           NH_{2}
+      / \\                         |
+     /   \\                    N   ^
+     ||   |-CONH_{2}          //\ / \\
+     ||   |                   |  ||  N
+     \   //                   |  ||  |
+       N_{+}                  N--+   |
+       |                      |   \//
+       |                      |    N
+    H--C------+            H--C------+
+       |      |               |      |
+    H--C--OH  |            H--C--OH  |
+       |      O               |      O
+    H--C--OH  |            H--C--OH  |
+       |      |               |      |
+    H--C------+   O     O  H--C------+
+       |          ||    ||    |
+       CH_{2}--O--P--O--P--O--CH_{2}
+                  |     |
+                  O-    OH
+
+                 Coenzyme I
+
+[Illustration: Figure 20.--FRITZ A. LIPMANN (b. 1899) shared with Hans
+Adolf Krebs the Nobel Prize in Medicine and Physiology in 1953 for his
+work on coenzyme A. He discovered acetyl phosphate as the substance in
+bacteria, which transfers phosphate to adenylic acid.]
+
+[Illustration: Figure 21.--ALEXANDER R. TODD (b. 1907) received the
+Nobel Prize in Chemistry in 1957 for his research on nucleotides. He
+determined the position of the phosphate groups in the molecule and
+confirmed it by synthesis of dinucleotide phosphates.]
+
+Its function is connected with the transfer of hydrogen between
+intermediates formed through phosphate-transferring enzymes.
+Fermentation proceeds by a cascade of processes, in which phosphate
+groups swing back and forth, and equilibria between ATP with ADP play a
+major role.
+
+Many of the enzymes are closely related to vitamins. Thus, cocarboxylase
+A, which takes part in the separation of carbon dioxide from an
+intermediate fermentation product, is the phosphate of vitamin B_{1}.
+Others of the B vitamins contain phosphate groups, for example those of
+the B_{2} and B_{6} group, and in B_{12}, one lonely phosphate forms a
+bridge in the large molecule that contains one atom of cobalt:
+C_{63}H_{90}N_{14}O_{14}PCo. The formation of vitamin A from carotine
+occurs under the influence of ATP.
+
+The first stages in fermentation are like those in respiration, which
+ends with carbon dioxide and water. These two are the materials for the
+reverse process in photosynthesis. When light is absorbed by the
+chlorophyll of green plants, one of the initial reactions is a transfer
+of hydrogen from water to a triphosphopyridine nucleotide, which later
+acts to reduce the carbon dioxide. Under the influence of ATP,
+phosphoglyceric acid is synthesized and further built up by way of
+carbohydrate phosphates to hexose sugars and finally to starch. In many
+starchy fruits, a small proportion of phosphate remains attached to the
+end product.
+
+The synthesis of proteins is under the control of deoxyribonucleic acid
+or ribonucleic acid, abbreviated by the symbols DNA and RNA. The genes
+in the nucleus are parts of a giant DNA molecule. RNA is a universal
+constituent of all living cells. Where protein synthesis is intense, the
+content in RNA is high. Thus, the spinning glands of silkworms are
+extraordinarily rich in RNA.[37]
+
+In his research on the radioactive isotope P^32, George de Hevesy gained
+some insight into the surprising mobility of phosphates in organisms: "A
+phosphate radical taken up with the food may first participate in the
+phosphorylation of glucose in the intestinal mucose, soon afterwards
+pass into the circulation as free phosphate, enter a red corpuscle,
+become incorporated with an adenosine triphosphoric-acid molecule,
+participate in a glycolytic process going on in the corpuscle, return to
+circulation, penetrate into the liver cells, participate in the
+formation of a phosphatide molecule, after a short interval enter the
+circulation in this form, penetrate into the spleen, and leave this
+organ after some time as a constituent of a lymphocyte. We may meet the
+phosphate radical again as a constituent of the plasma, from which it
+may find its way into the skeleton."[38] Much has been added in the last
+30 years to complete this picture in many details and to extend it to
+other biochemical processes, including even the changes of the pigments
+in the retina in the visual process, or in the conversion of chemical
+energy to light by bacteria and insects.
+
+
+
+
+Medicines and Poisons
+
+
+In the delicate balance of these processes, disturbances may occur which
+can be remedied by specific phosphate-containing medicines. Thus,
+adenosine phosphate has been recommended in cases of angina pectoris
+and marketed under trade names like sarkolyt, or in compounds named
+angiolysine. A considerable number of physiologically active organic
+phosphates can be found in the patent literature.[39] Yeast itself is
+considered to be a valuable food additive.
+
+On the other hand, there are phosphate compounds that act as poisons.
+One group of such compounds was discovered in 1929 by W. Lange, who
+wrote: "Of interest is the strong action of mono-fluorophosphate esters
+on the human body--the effect is produced by very small quantities."[40]
+Diisopropyl fluorophosphate has since become a potential agent for
+chemical warfare. It inactivates an enzyme which controls the
+transmission of nerve impulses to muscle, acetylcholine esterase.
+
+Organic esters of phosphoric acids are used as insecticides. The
+hexa-ethylester of tetraphosphoric acid, prepared by Gerhard Schrader by
+heating triethylphosphate with phosphorus oxychloride,[41] actually
+contains tetraethylpyrophosphate (TEPP) among others. Bayer's Dipterex,
+the dimethyl ester of 2,2,2-trichloro-1-hydroxyethyl-phosphonate, has
+been modified to dimethyl-2,2-dichlorovinyl-phosphate and is especially
+active against the oriental fruit fly.[42]
+
+[Illustration: Figure 22.--ARTHUR KORNBERG (b. 1918) AND SEVERO OCHOA
+(b. 1905) shared the Nobel Prize in Medicine and Physiology in 1959.
+Kornberg received it for research on the biological synthesis of
+deoxyribonucleic acid. In particular, he found that four triphosphate
+components and a small amount of the end product as a "template" had to
+be present for the enzymatic synthesis. Ochoa received his share of the
+prize for research in ribonucleic acid and deoxyribonucleic acid. In
+particular, Ochoa synthesized polyribonucleotides and used the
+radioactive isotope, P^{32}. The synthetic polyribonucleotides were
+found to resemble the natural substances in all essentials.]
+
+        Cl H  O
+        |  | || OCH_{3}
+        |  | ||/
+    Cl--C--C--P             Bayer's L 13/59
+        |  |   \              (Dipterex)
+        |  |    OCH_{3}
+        Cl OH
+
+    (CH_{3})_{2}N O     O  N(CH_{3})_{2}
+                 \||    ||/
+                  P--O--P                  Schradan
+                 /       \
+    (CH_{3})_{2}N         N(CH_{3})_{2}
+
+         Octamethylpyrophosphoramide
+
+[Illustration: Figure 23.--MELVIN CALVIN (b. 1911) received the Nobel
+Prize in Chemistry in 1961 for his research in photosynthesis, in which
+he specified the function of phosphoglyceric acid as an intermediate in
+the synthesis of carbohydrates from carbon dioxide and water by green
+plants.]
+
+The story of phosphorus, which began 300 years ago, has acquired new
+importance in this century. Many scientists have contributed to it: 13
+of them have received Nobel Prizes for work directly bearing on the
+chemical and biological importance of phosphorus compounds. In
+chronological order, they are: Eduard Buchner, Albrecht Kossel, Otto
+Meyerhof, Arthur Harden, Hans von Euler-Chelpin, George de Hevesy, Carl
+F. Cori, Gerty T. Cori, Fritz Lipmann, Lord Alexander Todd, Arthur
+Kornberg, Severo Ochoa, and Melvin Calvin. The developers of industrial
+production and commercial utilization of phosphate compounds have had
+other rewards.
+
+Some impression of the continuing growth in this field[43] can be gained
+from the following data.
+
+PHOSPHATE ROCK
+
+annually "sold or used by producer" in the United States in million long
+tons (2,240 lbs.)
+
+    1880    0.2
+    1890    0.5
+    1900    1.5
+    1910    2.655
+    1920    4.104
+    1930    3.926
+    1940    4.003
+    1945    5.807
+    1950   11.114
+    1955   12.265
+    1955   (world: about 56)
+    1960   17.202
+    1962   19.060
+
+Sources: U.S. Bureau of the Census. _Historical Statistics of the United
+States 1789-1945_ (1949); _Statistical Abstract of the United States._
+
+ELEMENTAL PHOSPHORUS
+
+annually produced in the United States in short tons (2,000 lbs.)
+
+    1939     43,000
+    1944     85,679
+    1950    153,233
+    1956    312,200
+    1958    335,750
+    1959    366,350
+    1960    409,096
+    1961    430,617
+    1962    451,970
+
+Source: U.S. Department of Commerce.
+
+
+
+
+FOOTNOTES:
+
+
+[1] WILHELM HOMBERG, _Mémoires Académie, 1666-1699_ (Paris, 1730), vol.
+10, under date of April 30, 1692, pp. 57-61.
+
+[2] FORTUNIO LICETUS, _Lithiophosphorus sive de lapide Bononiensi_
+(Venice, 1640).
+
+[3] Cited in PETER JOSEPH MACQUER _Chymisches Wörterbuch_, 2nd ed.
+(Leipzig: Weidmann, 1789), vol. 4, p. 508, footnote "c" as "Kletwich (de
+phosph. liqu. et solid. 1689, Thes. II)."
+
+[4] FERDINAND HOEFER, _Histoire de la Chimie_ (Paris, 1843), vol. 1, p.
+339.
+
+[5] G. W. VON LEIBNIZ, _Mémoires Académie_ (Paris, 1682); _Akademie der
+Wissenschaften, Miscellanea Berolinensia_ (Berlin, 1710), vol. 1, p. 91.
+
+[6] JEAN HELLOT, _Mémoires Académie 1737_ (Paris, 1766), under date of
+November 13, 1737, pp. 342-378.
+
+[7] MACQUER, op. cit. (footnote 3), p. 551.
+
+[8] A. S. MARGGRAF, _Akademie der Wissenschaften, Miscellanea
+Berolinensia_ (Berlin, 1743), vol. 7, 342 ff.; see also WILHELM OSTWALD
+_Klassiker der Exakten Naturwissenschaften_ (Leipzig: Engelmann, 1913),
+no. 187.
+
+[9] G. HANCKEWITZ, [Hankwitz], _Philosophical Transactions of the Royal
+Society of London_, 1724-1734, abridged (London, 1809), vol. 7, pp.
+596-602.
+
+[10] ANTOINE LAURENT LAVOISIER, "Sur la Combustion du Phosphore de
+Kunckel, Et sur la nature de l'acide qui resulte de cette Combustion,"
+_Mémoires Académie 1777_, (Paris, 1780), pp. 65-78.
+
+[11] GUYTON DE MORVEAU and others, _Méthode de Nomenclature Chimique_,
+Proposée par MM. de Morveau, Lavoisier, Bertholet, & de Fourcroy (Paris,
+1787), plate 9.
+
+[12] MACQUER, op. cit. (footnote 3), p. 513.
+
+[13] MARIE BOAS, _Robert Boyle and Seventeenth Century Chemistry_ (New
+York: Cambridge University Press, 1958), p. 226; see also WYNDHAM MILES,
+"The History of Dr. Brand's Phosphorus Elementarus," _Armed Forces
+Chemical Journal_ (November-December 1958), p. 25.
+
+[14] ARCHIBALD CLOW and NAN L. CLOW, _The Chemical Revolution_ (London:
+Batchworth Press, 1952), p. 451.
+
+[15] ÉMILE KOPP, _Comptes-rendus hebdomadaires des Séances de l'Académie
+des Sciences, Paris_ (1844), vol. 18, p. 871; WILHELM HITTORF, _Annalen
+der Chemie und Pharmazie_, suppl. to vol. 4, p. 37; ANTON SCHRÖTTER,
+_Annales de Chimie et de Physique_, series 3, vol. 24 (1848), p. 406;
+see also Schrötter's report on "Phosphor und Zündwaaren" in A. W. VON
+HOFMANN, _Bericht über die Entwicklung der Chemischen Industrie_
+(Braunschweig: Vieweg, 1875), pp. 219-246.
+
+[16] R. GLAUBER, _Furni Novi Philosphici_ (Amsterdam, 1649), vol. 2, pp.
+12 ff.
+
+[17] HERMANN SCHELENZ, _Geschichte der Pharmazie_ (Berlin: Springer,
+1904), p. 598.
+
+[18] J. PERSONNE, _Comptes-rendus ..._, Paris (1869), vol. 68, pp.
+543-546.
+
+[19] A. WURTZ, _Dictionnaire de Chimie_ (Paris, 1876), vol. 2, part 2,
+p. 951.
+
+[20] KARL W. SCHEELE, _Nachgelassene Briefe und Aufzeichnungen_, edit.
+A. E. Nordenskiöld (Stockholm: Norstedt, 1892), pp. 38, 144.
+
+[21] J. J. BERZELIUS, _Lehrbuch_, transl. F. Wöhler (Dresden, 1827),
+vol. 3, part 1, p. 96.
+
+[22] THOMAS GRAHAM, _Philosophical Transactions of the Royal Society of
+London_ (1833), pp. 253-284.
+
+[23] JUSTUS LIEBIG'S _Annalen der Pharmacie_ (1838), vol. 26, p. 113 ff.
+
+[24] A. WURTZ, _Annales de Chimie et de Physique_, series 3, vol. 16
+(1846), p. 190.
+
+[25] CARROLL D. WRIGHT, _The Phosphate Industry in the United States_,
+sixth special report of the Commissioner of Labor (Washington, 1893).
+
+[26] J. STOKLASA, _Biochemischer Kreislauf des Phosphat-Ions im Boden,
+Centralblatt für Bakteriologie ..._ (Jena: Fischer, March 22, 1911),
+vol. 29, nos. 15-19.
+
+[27] N. T. GOBLEY, _Comptes-rendus_ ..., Paris (1845), vol. 21, p. 718.
+
+[28] A. WURTZ, _Comptes-rendus_ ..., Paris (1868), vol. 66, p. 772.
+
+[29] L. THUDICHUM, _Die chemische Constitution des Gehirns des Menschen
+und der Tiere_ (1901); see also H. WITTCOFF, THE PHOSPHATIDES (New York:
+Reinhold, 1951).
+
+[30] WILLIAM CROOKES, _British Association for the Advancement of
+Science, Reports_ (1887), sec. B, p. 573.
+
+[31] J. E. COURTOIS and A. LINO, _Progress in the Chemistry of Organic
+Natural Products_, edit. L. Zechmeister (Vienna: Springer Verlag, 1961),
+vol. 19, p. 316-373.
+
+[32] A. WURT, _Dictionnaire de Chimie_, supp. part 2, [n.d.] p. 1087; A.
+KOSSEL, _Zeitschrift für physiologische Chemie_, series 3 (1879), p.
+284.
+
+[33] ALEXANDER TODD, _Les Prix Nobel en 1957_ (Stockholm).
+
+[34] HANS VON EULER-CHELPIN, _Les Prix Nobel en 1929_ (Stockholm).
+
+[35] O. MEYERHOF and E. LUNDSGAARD, _Naturwissenschaften_ (Berlin,
+1930), vol. 18, pp. 330, 787.
+
+[36] K. LOHMANN, _Naturwissenschaften_ (Berlin, 1929), vol. 17, p. 624;
+C. H. FISKE and Y. SUBBAROW, _Science_ (Washington, 1929), vol. 70, p.
+381 f.
+
+[37] J. BRACHET, _Scientia, Revista di Scienza_ (1960), vol. 95, p. 119.
+
+[38] GEORGE DE HEVESY, _Les Prix Nobel en 1940_ (Stockholm). See also
+EDUARD FARBER, _Nobel Prize Winners in Chemistry_, 2nd ed. (New York:
+Schuman, 1963), p. 179.
+
+[39] See, e.g., _Chemical Week_, vol. 77 (September 3, 1955), p. 79 f.;
+J. BOLLE, _Chimie et Industrie_ (1960), vol. 83, p. 252.
+
+[40] W. LANGE, _Berichte der Deutschen Chemischen Gesellschaft_ (Berlin,
+1929), vol. 62, p. 793; vol. 65 (1932), p. 1598.
+
+[41] GERHARD SCHRADER, U.S. patent 2,336,302 of 1943 (priority in
+Germany, 1938); S. A. HALL and M. JACOBSON, _Industrial and Engineering
+Chemistry_ (1943), vol. 40, p. 694.
+
+[42] A. M. MATTSEN and others, _Journal of Agriculture and Food
+Chemistry_ (1955), vol. 3, p. 319.
+
+[43] JOHN B. VAN WAZER, _Phosphorus and its Compounds_, 2 vols.
+(vol. 1, _Chemistry_; vol. 2 _Technology, Biological Functions and
+Applications_, New York: Interscience, 1958, 1961.
+
+       *       *       *       *       *
+
+U.S. GOVERNMENT PRINTING OFFICE: 1965
+
+For sale by the Superintendent of Documents, U.S. Government Printing
+Office Washington, D.C. 20402--Price 25 cents
+
+
+
+
+INDEX
+
+
+Aristotle, 179
+
+
+Baeyer, Adolf, 193
+
+Bechil, Achild, 179
+
+Berthelot, Marcellin, 189
+
+Berzelius, Jöns Jakob, 182
+
+Black and Bell, plant at Stratford, 182
+
+Boussingault, Jean Baptiste, 185
+
+Boyle, Robert, 178, 179
+
+Brand, H., 178, 179
+
+Buchner, Hans, 197, 200
+
+
+Calvin, Melvin, 200
+
+Casciarolo, Vicenzo, 179
+
+Chevreul, Michel, 189
+
+Cori, Carl F., 200
+
+Cori, Gerti T., 200
+
+Crookes, William, 192
+
+
+Davy, Sir Humphry, 185
+
+De Hevesy, George, 198, 200
+
+De la Vega, Garcilaso, 185
+
+De Saussure, Théodore, 185
+
+
+Euler-Chelpin, Hans von, 197, 200
+
+
+Fernelius, Jean, 179
+
+Feulgen, Robert, 193
+
+Fischer, Emil, 193
+
+
+Gahn, Johann Gottlieb, 182
+
+Gay-Lussac, Joseph Louis, 182
+
+Gobley, Nicolas Théodore, 191
+
+Graham, Thomas, 182, 183, 185
+
+
+Hankwitz, Gottfried, 180
+
+Harden, Arthur, 197, 200
+
+Hartmann, Immanuel Peter, 181
+
+Hellot, Jean, 180
+
+Henry II, King of France, 179
+
+Hittorf, Wilhelm, 181
+
+Hoefer, Ferdinand, 179
+
+Holmberg, Wilhelm, 178
+
+Hoppe-Seyler, Felix, 193
+
+Humboldt, Alexander von, 185
+
+Huygens, Christiaan, 179
+
+
+Incas, 185
+
+
+Kletwich, Johann Christopher, 179
+
+Koppe, Émile, 181
+
+Kornberg, Arthur, 200
+
+Kossel, Albrecht, 200
+
+Kraft, Johann Daniel, 179
+
+Kramer, Dr. ----, 181
+
+Kunckel, Johann, 179
+
+
+Lange, W., 199
+
+Lavoisier, Antoine Laurent, 181, 185
+
+Laws, John Bennet, 186
+
+Leibnitz, Gottfried Wilhelm von, 179
+
+Lennox, Charles, third Duke of Richmond, 185
+
+Leonhardi, Johann Gottfried, 179
+
+Levine, Phoebus Aaron Theodor, 193
+
+Liebig, Justus, 183, 185, 186
+
+Liebreich, Oscar, 191
+
+Lipmann, Fritz, 200
+
+London, E. S., 193
+
+
+Macquer, Peter Joseph, 180
+
+Marggraf, Andreas Sigismund, 180
+
+Meyerhof, Otto, 194, 200
+
+Miescher, Johann Friedrich, 192
+
+Muspratt, James, 186
+
+
+Nietzsche, Friedrich, 186, 187, 189
+
+
+Ochoa, Severo, 200
+
+
+Pelouze, Théophile Juste, 189
+
+
+Rouelle, Guillaume François, 181
+
+
+Scheele, Karl W., 182
+
+Schmiedeberg, Oswald, 193
+
+Schrader, Gerhard, 199
+
+Schrötter, Anton, 181
+
+Stoklasa, Julius, 186
+
+Strecker, Adolf Friedrich, 191
+
+
+Thudichum, Ludwig, 192
+
+Todd, Lord Alexander, 200
+
+
+Willm, Edmond, 182
+
+Willstätter, Richard, 191
+
+Wurtz, Adolphe, 185, 191
+
+
+
+
+Transcriber's Notes
+
+
+The following typographical errors have been corrected:
+
+    Page 180 "_Abfällen_, Vieweg, Braunschweig," - had "Viewig".
+    Page 188 "wires _d_ from the dynamo D" - had "dynano".
+    Page 191 "phosphate are attached, for example," - had "attached, For".
+    Page 192 "But phosphatides occur" - had "phosphatide soccur".
+    Page 193 "the nucleic acid from the thymus" - had "nucleidic".
+    Page 199 "acetylcholine esterase." - had "acetylcholin".
+    Page 200 "George de Hevesy, Carl F. Cori," - comma added after Hevesy.
+    Footnote [39] "See, e.g., _Chemical Week_, vol. 77" - had "See. e.g."
+    Index Entry: "Gahn, Johann Gottlieb, 182" - had "Gähn"
+
+The spelling of "Bertholet" [Claude Louis Berthollet] is as given on the
+original title page of the work referenced in this paper.
+
+Inconsistent hyphenation of chemical names has been retained.
+
+
+
+
+
+End of the Project Gutenberg EBook of History of Phosphorus, by Eduard Farber
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+<pre>
+
+The Project Gutenberg EBook of History of Phosphorus, by Eduard Farber
+
+This eBook is for the use of anyone anywhere at no cost and with
+almost no restrictions whatsoever.  You may copy it, give it away or
+re-use it under the terms of the Project Gutenberg License included
+with this eBook or online at www.gutenberg.org
+
+
+Title: History of Phosphorus
+
+Author: Eduard Farber
+
+Release Date: September 20, 2010 [EBook #33766]
+
+Language: English
+
+Character set encoding: ISO-8859-1
+
+*** START OF THIS PROJECT GUTENBERG EBOOK HISTORY OF PHOSPHORUS ***
+
+
+
+
+Produced by Chris Curnow, Joseph Cooper, Louise Pattison
+and the Online Distributed Proofreading Team at
+https://www.pgdp.net
+
+
+
+
+
+
+</pre>
+
+
+<div class="tnote">
+<h3>Transcriber&rsquo;s Notes</h3>
+
+<p>This is Paper 40 from the Smithsonian Institution United States
+National Museum Bulletin 240, comprising Papers 34-44, which will
+also be available as a complete e-book.</p>
+
+<p>The front material, introduction and relevant index entries from
+the Bulletin are included in each single-paper e-book.</p>
+
+<p><a href="#corrections_37">Corrections</a> to typographical errors are underlined
+<ins class="mycorr" title="Original: like thsi">like this</ins>. Mouse over to view the original text.</p>
+
+</div>
+
+
+<hr style="width: 65%;" />
+
+<h1>SMITHSONIAN INSTITUTION<br />
+UNITED STATES NATIONAL MUSEUM<br />
+BULLETIN 240</h1>
+
+<div class="figright">
+  <img src="images/i_002.png" alt="Smithsonian Press Logo" title="" />
+</div>
+
+<p class="right" style="clear:both;">SMITHSONIAN PRESS<br /></p>
+
+<p>MUSEUM OF HISTORY AND TECHNOLOGY</p>
+
+<p style="font-size: 2em; font-weight: bold;" class="smcap">Contributions<br />
+From the<br />
+Museum<br />
+of History and<br />
+Technology</p>
+
+<p style="font-size: 1.25em;"><em>Papers 34-44<br />
+On Science and Technology</em></p>
+
+<p>SMITHSONIAN INSTITUTION &middot; WASHINGTON, D.C. 1966</p>
+
+<hr style="width: 65%;" />
+
+<p class="center" style="font-size: 1.25em;"><em>Publications of the United States National Museum</em></p>
+
+<p>The scholarly and scientific publications of the United States National Museum
+include two series, <cite>Proceedings of the United States National Museum</cite> and <cite>United States
+National Museum Bulletin</cite>.</p>
+
+<p>In these series, the Museum publishes original articles and monographs dealing
+with the collections and work of its constituent museums&mdash;The Museum of Natural
+History and the Museum of History and Technology&mdash;setting forth newly acquired
+facts in the fields of anthropology, biology, history, geology, and technology. Copies
+of each publication are distributed to libraries, to cultural and scientific organizations,
+and to specialists and others interested in the different subjects.</p>
+
+<p>The <cite>Proceedings</cite>, begun in 1878, are intended for the publication, in separate
+form, of shorter papers from the Museum of Natural History. These are gathered
+in volumes, octavo in size, with the publication date of each paper recorded in the
+table of contents of the volume.</p>
+
+<p>In the <cite>Bulletin</cite> series, the first of which was issued in 1875, appear longer, separate
+publications consisting of monographs (occasionally in several parts) and volumes
+in which are collected works on related subjects. <cite>Bulletins</cite> are either octavo or
+quarto in size, depending on the needs of the presentation. Since 1902 papers relating
+to the botanical collections of the Museum of Natural History have been
+published in the <cite>Bulletin</cite> series under the heading <cite>Contributions from the United States
+National Herbarium</cite>, and since 1959, in <cite>Bulletins</cite> titled &ldquo;Contributions from the Museum
+of History and Technology,&rdquo; have been gathered shorter papers relating to the collections
+and research of that Museum.</p>
+
+<p>The present collection of Contributions, Papers 34-44, comprises Bulletin 240.
+Each of these papers has been previously published in separate form. The year of
+publication is shown on the last page of each paper.</p>
+
+<p class="right"><span class="smcap">Frank A. Taylor</span><br />
+<em>Director, United States National Museum</em></p>
+
+<hr style="width: 65%;" />
+<p><span class="pagenum"><a name="Page_177" id="Page_177">[Pg 177]</a></span></p>
+
+<h1><a name="Paper_40" id="Paper_40"></a><span class="smcap">Contributions from<br />
+The Museum of History and Technology</span>:<br />
+<span class="smcap">Paper</span> 40<br />
+<br /><br />
+<span class="smcap">History of Phosphorus</span>
+</h1>
+<p><span class="rnum" style="font-size: larger;">
+<em>Eduard Farber</em></span><br /><br/></p>
+
+<p><span class="rnum">THE ELEMENT FROM ANIMALS AND PLANTS&nbsp; &nbsp;<a href="#Page_178">178</a></span><br /></p>
+<p><span class="rnum">EARLY USES&nbsp; &nbsp;<a href="#Page_181">181</a></span><br /></p>
+<p><span class="rnum">CHEMICAL CONSTITUTION OF PHOSPHORIC ACIDS&nbsp; &nbsp;<a href="#Page_182">182</a></span><br /></p>
+<p><span class="rnum">PHOSPHATES AS PLANT NUTRIENTS&nbsp; &nbsp;<a href="#Page_185">185</a></span><br /></p>
+<p><span class="rnum">FROM INORGANIC TO ORGANIC PHOSPHATES&nbsp; &nbsp;<a href="#Page_187">187</a></span><br /></p>
+<p><span class="rnum">PHOSPHATIDES AND PHOSPHAGENS&nbsp; &nbsp;<a href="#Page_189">189</a></span><br /></p>
+<p><span class="rnum">NUCLEIN AND NUCLEIC ACIDS&nbsp; &nbsp;<a href="#Page_192">192</a></span><br /></p>
+<p><span class="rnum">PHOSPHATES IN BIOLOGICAL PROCESSES&nbsp; &nbsp;<a href="#Page_197">197</a></span><br /></p>
+<p><span class="rnum">MEDICINES AND POISONS&nbsp; &nbsp;<a href="#Page_198">198</a></span><br /></p>
+
+<hr style="width: 65%;" />
+<p><span class="pagenum"><a name="Page_178" id="Page_178">[Pg 178]</a></span></p>
+
+<p>&nbsp;<span class="rnum"><em><big>Eduard Farber</big></em></span><br /></p>
+
+<h2><big>HISTORY OF PHOSPHORUS</big></h2>
+
+<div class="blockquotn"><p><i>The &ldquo;cold light&rdquo; produced by phosphorus caused it to be
+considered a miraculous chemical for a long time after its
+discovery, about 1669. During the intervening three centuries
+numerous other chemical miracles have been found, yet
+phosphorus retains a special aura of universal importance in
+chemistry. Many investigators have occupied themselves with
+this element and its diverse chemical compounds. Further
+enlightenment and insight into the ways of nature can be
+expected from these efforts.</i></p>
+
+<p><i>Not only is the story of phosphorus a major drama in the
+history of chemistry; it also illustrates, in a spectacular
+example, the growth of this science through the discovery of
+connections between apparently unrelated phenomena, and the
+continuous interplay between basic science and the search for
+practical usage.</i></p>
+
+<p><span class="smcap">The Author</span>: <i>Eduard Farber is a research professor at American
+University, Washington, D.C., and has been associated with the
+Smithsonian Institution as a consultant in chemistry.</i></p></div>
+
+
+<p>When phosphorus was discovered, nearly three centuries ago, it was
+considered a miraculous thing. The only event that provoked a similar
+emotion was the discovery of radium more than two centuries later. The
+excitement about the <i>Phosphorus igneus</i>, Boyle&rsquo;s <i>Icy Noctiluca</i>, was
+slowly replaced by, or converted into, chemical research. Yet, if we
+would allow room for emotion in research, we could still be excited
+about the wondrous substance that chemical and biological work continues
+to reveal as vitally important. It is a fundamental plant nutrient, an
+essential part in nerve and brain substance, a decisive factor in muscle
+action and cell growth, and also a component in fast-acting, powerful
+poisons. The importance of phosphorus was gradually recognized and the
+means by which this took place are characteristic and similar to other
+developments in the history of science. This paper was written in order
+to summarize these various means which led to the highly complex ways of
+present research.</p>
+
+<hr style="width: 65%;" />
+
+<h3>The Element from Animals and Plants</h3>
+
+<p>It was a little late to search for the philosophers&rsquo; stone in 1669, yet
+it was in such a search that phosphorus was discovered. Wilhelm Homberg
+(1652-1715) described it in the following manner: Brand, <span class="pagenum"><a name="Page_179" id="Page_179">[Pg 179]</a></span>&ldquo;a man little
+known, of low birth, with a bizarre and mysterious nature in all he
+did, found this luminous matter while searching for something else. He
+was a glassmaker by profession, but he had abandoned it in order to be
+free for the pursuit of the philosophical stone with which he was
+engrossed. Having put it into his mind that the secret of the
+philosophical stone consisted in the preparation of urine, this man
+worked in all kinds of manners and for a very long time without finding
+anything. Finally, in the year 1669, after a strong distillation of
+urine, he found in the recipient a luminant matter that has since been
+called phosphorus. He showed it to some of his friends, among them
+Mister Kunkel [sic].&rdquo;<a name="FNanchor_1_1" id="FNanchor_1_1"></a><a href="#Footnote_1_1" class="fnanchor">[1]</a></p>
+
+<p>Neither the name nor the phenomenon were really new. Organic
+phosphorescent materials were known to Aristotle, and a lithophosphorus
+was the subject of a book published in 1640, based on a discovery made
+by a shoemaker, Vicenzo Casciarolo, on a mountain-side near Bologna in
+1630.<a name="FNanchor_2_2" id="FNanchor_2_2"></a><a href="#Footnote_2_2" class="fnanchor">[2]</a> Was the substance new which Brand showed to his friends? Johann
+Gottfried Leonhardi quotes a book of 1689 in which the author, Kletwich,
+claims that this phosphorus had already been known to Fernelius, the
+court physician of King Henri II of France (1154-1189).<a name="FNanchor_3_3" id="FNanchor_3_3"></a><a href="#Footnote_3_3" class="fnanchor">[3]</a> To the same
+period belongs the &ldquo;Ordinatio Alchid Bechil Saraceni philosophi,&rdquo; in
+which Ferdinand Hoefer found a distillation of urine with clay and
+carbonaceous material described, and the resulting product named
+escarbuncle.<a name="FNanchor_4_4" id="FNanchor_4_4"></a><a href="#Footnote_4_4" class="fnanchor">[4]</a> It would be worth looking for this source; although
+Bechil would still remain an entirely unsuccessful predecessor, it does
+seem strange that in all the distillations of arbitrary mixtures, the
+conditions should never before 1669 have been right for the formation
+and the observation of phosphorus.</p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i006.png" width="400" height="697" alt="Figure 1.&mdash;The alchemist discovers phosphorus. A painting
+by Joseph Wright (1734-1779) of Derby, England." title="Figure 1." />
+<p class="caption">Figure 1.&mdash;<span class="smcap">The alchemist discovers phosphorus.</span> A painting
+by Joseph Wright (1734-1779) of Derby, England.</p>
+</div>
+
+<p>For Brand&rsquo;s contemporaries at least, the discovery was new and exciting.
+The philosopher Gottfried Wilhelm von Leibniz (1646-1716) considered it
+important enough to devote some of his time (between his work as
+librarian in Hanover and Wolfenbüttel, his efforts to reunite the
+Protestant and the Catholic churches, and his duties as Privy Councellor
+in what we would call a Department of Justice) to a history of
+phosphorus. This friend of Huygens and Boyle tried to prove that Kunckel
+was not justified in claiming the discovery for himself.<a name="FNanchor_5_5" id="FNanchor_5_5"></a><a href="#Footnote_5_5" class="fnanchor">[5]</a> Since then,
+it has been shown that Johann Kunckel (1630-1703) actually worked out
+the method which neither Brand nor his friend Kraft wanted to disclose.
+Boyle also developed a method independently, published it, and
+instructed<span class="pagenum"><a name="Page_180" id="Page_180">[Pg 180]</a></span> Gottfried Hankwitz in the technique. Later on, Jean Hellot
+(1685-1765) gave a meticulous description of the details and a long
+survey of the literature.<a name="FNanchor_6_6" id="FNanchor_6_6"></a><a href="#Footnote_6_6" class="fnanchor">[6]</a></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i007.png" width="300" height="249" alt="Figure 2." title="Figure 2." />
+<p class="caption2">Figure 2.&mdash;<span class="smcap">Galley-oven</span>, 1869. The picture is a cross
+section through the front of the oven showing one of the 36 retorts, the
+receivers for the distillate, and the space in the upper story used for
+evaporating the mixture of acid solution of calcium phosphate and coal.
+(According to <span class="smcap">Anselme Payen</span>, <i>Précis de Chimie industrielle</i>, Paris,
+1849; reproduced from <span class="smcap">Hugo Fleck</span>, <i>Die Fabrikation chemischer Produkte
+aus thierischen Abfällen</i>, <a name="corr_40_1" id="corr_40_1"></a><ins class="mycorr" title="Original: Viewig">Vieweg</ins>, Braunschweig, 1862, page 80 of volume
+2, 2nd group, of <span class="smcap">P. Bolley&rsquo;s</span> <i>Handbuch der chemischen Technologie</i>.)</p>
+</div>
+
+<p>To obtain phosphorus, a good proportion of coal (regarded as a type of
+phlogiston) was added to urine, previously thickened by evaporation and
+preferably after putrefaction, and the mixture was heated to the highest
+attainable temperature. It was obvious that phlogiston entered into the
+composition of the distillation product. The question remained whether
+this product was generated <i>de novo</i>. In his research of 1743 to 1746,
+Andreas Sigismund Marggraf (1709-1782) provided the answer. He found the
+new substance in edible plant seeds, and he concluded that it enters the
+human system through the plant food, to be excreted later in the urine.
+He did not convince all the chemists with his reasoning. In 1789,
+Macquer wrote: &ldquo;There are some who, even at this time, hold that the
+phosphorical (&lsquo;phosphorische&rsquo;) acid generates itself in the animals and
+who consider this to be the &lsquo;animalistic acid.&rsquo;&rdquo;<a name="FNanchor_7_7" id="FNanchor_7_7"></a><a href="#Footnote_7_7" class="fnanchor">[7]</a></p>
+
+<p>Although Marggraf was more advanced in his arguments than these
+chemists, yet he was a child of his time. The luminescent and
+combustible, almost wax-like substance impressed him greatly. &ldquo;My
+thoughts about the unexpected generation of light and fire out of water,
+fine earth, and phlogiston I reserve to describe at a later time.&rdquo; These
+thoughts went so far as to connect the new marvel with alchemical wonder
+tales. When Marggraf used the &ldquo;essential salt of urine,&rdquo; also called
+<i>sal microcosmicum</i>, and admixed silver chloride (&ldquo;horny silver&rdquo;) to it
+for the distillation of phosphorus, he expected &ldquo;a partial conversion of
+silver by phlogiston and the added fine vitrifiable earth, but no trace
+of a more noble metal appeared.&rdquo;<a name="FNanchor_8_8" id="FNanchor_8_8"></a><a href="#Footnote_8_8" class="fnanchor">[8]</a></p>
+
+<p>Robert Boyle had already found that the burning of phosphorus produced
+an acid. He identified it by taste and by its influence on colored plant
+extracts serving as &ldquo;indicators.&rdquo; Hankwitz<a name="FNanchor_9_9" id="FNanchor_9_9"></a><a href="#Footnote_9_9" class="fnanchor">[9]</a> described methods for
+obtaining this acid, and Marggraf showed its chemical peculiarities.
+They did not necessarily establish phosphorus as a new element. To do
+that was not as important, at that time, as to conjecture on analogies
+with known substances. Underlying all its unique characteristics was the
+analogy of phosphorus with sulfur. Like sulfur, phosphorus can burn in
+two different ways, either slowly or more violently, and form two
+different acids. The analogy can, therefore, be extended to explain the
+results in both groups in the same way. In the process of burning, the
+combustible component is removed, and the acid originally combined with
+the combustible is set free. Whether the analogy should be pursued even
+further remained doubtful, although some suspicion lingered on for a
+while that phosphoric acid might actually be a modified sulfuric acid.
+Analogies and suspicions like these were needed to formulate new
+questions and stimulate new experiments. They are cited here for their
+important positive value in the historical development, and not for the
+purpose of showing how wrong these chemists were from our<span class="pagenum"><a name="Page_181" id="Page_181">[Pg 181]</a></span> point of
+view, a point of view which they helped to create.</p>
+
+<p>The widespread interest in the burning of sulfur and of phosphorus,
+naturally, caught Lavoisier&rsquo;s attention. In his first volume of
+<i>Opuscules Physiques et Chimiques</i> (1774), he devoted 20 pages to his
+experiments on phosphorus. He amplified them a few years later<a name="FNanchor_10_10" id="FNanchor_10_10"></a><a href="#Footnote_10_10" class="fnanchor">[10]</a> when
+he attributed the combustion to a combination of phosphorus with the
+&ldquo;eminently respirable&rdquo; part of air. In the <i>Méthode de Nomenclature
+Chimique</i> of 1787, the column of &ldquo;undecomposed substances&rdquo; lists sulfur
+as the &ldquo;radical sulfurique,&rdquo; and phosphorus, correspondingly, as the
+&ldquo;radical phosphorique.&rdquo; The acids are now shown to be compounds of the
+&ldquo;undecomposed&rdquo; radicals, the complete reversion of the previous concept
+of this relationship. A part of the old analogy remained as far as the
+acids are concerned: sulfuric acid corresponds to phosphoric; sulfurous
+acid to phosphorous acid with less oxygen than in the former.<a name="FNanchor_11_11" id="FNanchor_11_11"></a><a href="#Footnote_11_11" class="fnanchor">[11]</a></p>
+
+
+<hr style="width: 65%;" />
+
+<h3>Early Uses</h3>
+
+<p>In the 18th century, phosphorus was a costly material. It was produced
+mostly for display and to satisfy curiosity. Guillaume François Rouelle
+(1703-1770) demonstrated the process in his lectures, and, as Macquer
+reports, he &ldquo;very often&rdquo; succeeded in making it.<a name="FNanchor_12_12" id="FNanchor_12_12"></a><a href="#Footnote_12_12" class="fnanchor">[12]</a> Robert Boyle had
+the idea of using phosphorus as a light for underwater divers.<a name="FNanchor_13_13" id="FNanchor_13_13"></a><a href="#Footnote_13_13" class="fnanchor">[13]</a> A
+century later, &ldquo;instant lights&rdquo; were sold, with molten phosphorus as the
+&ldquo;igniter,&rdquo; but they proved cumbersome and unreliable.<a name="FNanchor_14_14" id="FNanchor_14_14"></a><a href="#Footnote_14_14" class="fnanchor">[14]</a> Because white
+phosphorus is highly poisonous, an active development of the use in
+matches occurred only after the conversion of the white modification
+into the red had been studied by Émile Kopp (1844), by Wilhelm Hittorf
+(1824-1914) and, in its practical application, by Anton Schrötter
+(1802-1875).<a name="FNanchor_15_15" id="FNanchor_15_15"></a><a href="#Footnote_15_15" class="fnanchor">[15]</a></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i010.png" width="300" height="252" alt="Figure 3." title="Figure 3." />
+<p class="caption2">Figure 3.&mdash;<span class="smcap">Distillation apparatus</span> (1849) for refining
+crude phosphorus. The crude phosphorus is mixed with sand under hot
+water, cooled, drained, and filled into the retort. The outlet of the
+retort, at least 6 cm. in diameter, is partially immersed in the water
+contained in the bucket. A small dish, made from lead, with an iron
+handle, receives the distilled phosphorus. (From <span class="smcap">Hugo Fleck</span>, <i>Die
+Fabrikation chemischer Produkte ...</i> page 90.)</p>
+</div>
+
+<p>The most exciting early use, however, was in medicine. It is not
+surprising that such a use was sought at that time. Any new material
+immediately became the hope of ailing mankind&mdash;and of striving
+inventors.<a name="FNanchor_16_16" id="FNanchor_16_16"></a><a href="#Footnote_16_16" class="fnanchor">[16]</a> Phosphorus was prescribed, in liniments with fatty oils
+or as solution in alcohol and ether, for external and internal
+application. A certain Dr. Kramer found it efficient against epilepsy
+and melancholia (1730). A Professor Hartmann recommended it against
+cramps.<a name="FNanchor_17_17" id="FNanchor_17_17"></a><a href="#Footnote_17_17" class="fnanchor">[17]</a> However, in the growing<span class="pagenum"><a name="Page_182" id="Page_182">[Pg 182]</a></span> production of phosphorus for
+matches, the workers experienced the poisonous effects. In the plant of
+Black and Bell at Stratford, this was prevented by inhaling turpentine.
+Experiments on dogs were carried out to show that poisoning by
+phosphorus could be remedied through oil of turpentine.<a name="FNanchor_18_18" id="FNanchor_18_18"></a><a href="#Footnote_18_18" class="fnanchor">[18]</a></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i011.png" width="300" height="297" alt="Figure 4." title="Figure 4." />
+<p class="caption2">Figure 4.&mdash;<span class="smcap">Apparatus for converting white phosphorus</span> into
+the red allotropic form, 1851. Redistilled phosphorus is heated in the
+glass or porcelain vessel (g) which is surrounded by a sandbath (e) and
+a metal bath (b). Vessel (j) is filled with mercury and water; together
+with valve (k), it serves as a safety device. The alcohol lamp (l) keeps
+the tube warm against clogging by solidified vapors. Because of hydrogen
+phosphides, the operation, carried out at 260° C., had to be watched
+very carefully. (According to Arthur Albright, 1851; reproduced from
+<span class="smcap">Hugo Fleck</span>, <i>Die Fabrikation chemischer Produkte ...</i>, page 112.)</p>
+</div>
+
+<hr style="width: 65%;" />
+
+<h3>Chemical Constitution of Phosphoric Acids</h3>
+
+<p>In a long article on phosphorus, Edmond Willm wrote in 1876: &ldquo;For a
+century, urine was the only source from which phosphorus was obtained.
+After Gahn, in 1769, recognized the presence of phosphoric acid in
+bones, Scheele indicated the procedure for making phosphorus from
+them.&rdquo;<a name="FNanchor_19_19" id="FNanchor_19_19"></a><a href="#Footnote_19_19" class="fnanchor">[19]</a> Actually, Gahn used at first hartshorn (<i>Cornu cervi
+ustum</i>), and Scheele doubted, until he checked it himself, that his
+esteemed friend was right. A few years later, Scheele corrected Gahn&rsquo;s
+assumption that the <i>sal microcosmicum</i> was an ammonia salt; instead, it
+is &ldquo;a tertiary neutral salt, consisting of <i>alkali minerali fixo</i> (i.e.,
+sodium), <i>alkali volatili</i>, and <i>acido phosphori</i>.&rdquo;<a name="FNanchor_20_20" id="FNanchor_20_20"></a><a href="#Footnote_20_20" class="fnanchor">[20]</a></p>
+
+<p>In the years after 1770, phosphorus was discovered in bones and many
+other parts of various animals. Treatment with sulfuric acid decomposed
+these materials into a solid residue and dissolved phosphoric acid. Many
+salts of this acid were produced in crystalline form. Heat resistance
+had been considered one of the outstanding characteristics of phosphoric
+acid. Now, however, in the processes of drying and heating certain
+phosphates, it became clear that three kinds of phosphoric acids could
+be produced: <i>ortho</i>, <i>pyro</i>, and <i>meta</i>.</p>
+
+<p>Berzelius cited these acids as examples of compounds which are <span style="text-transform:lowercase;" class="smcap">ISOMERIC</span>.
+This word was intended to designate compounds which contain the same
+number of atoms of the same elements but combined in different manners,
+thereby explaining their different chemical properties and crystal
+forms. It was in 1830 that Berzelius propounded this companion of the
+concept, <span style="text-transform:lowercase;" class="smcap">ISOMORPHISM</span>, which was to collect all cases of equal crystal
+form in compounds in which equal numbers of atoms of different elements
+are put together in the same manner. Together, the two concepts of
+isomerism and isomorphism seemed to cover all the known exceptions from
+the simplest assumption as to specificity and chemical composition.</p>
+
+<p>However, only a few years later Thomas Graham (1805-1869) proved that
+the three phosphoric acids are not isomeric. He used the proportion of 2
+P to 5 O in the oxide which Berzelius had thought justified at least
+until &ldquo;an example of the contrary could be sufficiently
+established.&rdquo;<a name="FNanchor_21_21" id="FNanchor_21_21"></a><a href="#Footnote_21_21" class="fnanchor">[21]</a> Refining the techniques of Gay-Lussac (1816) and
+several other investigators, Graham characterized the three phosphoric
+acids as &ldquo;a terphosphate, a biphosphate, and phosphate of water.&rdquo;
+Actually, this was the wrong terminology for what he meant and
+formulated as trihydrate, bihydrate, and monohydrate of phosphorus
+oxide. In<span class="pagenum"><a name="Page_183" id="Page_183">[Pg 183]</a></span> his manner of writing the formulas, each dot over the symbol
+for the element was to indicate an atom of oxygen; thus, he wrote:</p>
+
+<p class="mono" style="margin-bottom:0px; margin-left: 20%;">... :: &nbsp; .. ... &nbsp; &nbsp; &nbsp;.&nbsp;.</p>
+<p style="margin-top:0px; margin-left: 20%;"><span class="mono">&nbsp;H<sup>3</sup> &nbsp;P &nbsp; &nbsp;H<sup>2</sup> P &nbsp; and &nbsp;H P.</span><a name="FNanchor_22_22" id="FNanchor_22_22"></a><a href="#Footnote_22_22" class="fnanchor">[22]</a></p>
+
+<div class="figcenter" style="width: 650px;">
+
+<div class="figleft" style="width: 300px;">
+<img src="images/i013a.png" width="300" height="438" alt="Figure 5." title="Figure 5." />
+<p class="caption2">Figure 5.&mdash;<span class="smcap">Oven for the calcination of bones</span>, about 1870.
+&ldquo;The operation is carried out in a rather high oven, such as shown....
+The fresh bones are thrown in at the top of the oven, B. First, fuel in
+chamber F is lighted, and a certain quantity of bones is burnt on the
+grid D. When these bones are burning well, the oven is gradually filled
+with bones, and the combustion maintains itself without addition of
+other fuel. A circular gallery, C, surrounds the bottom of the oven and
+carries the products of combustion into the chimney, H. The calcined
+bones are taken out at the lower opening, G, by removing the bars of
+grid B.&rdquo; (Translation of the description from <span class="smcap">Figuier</span>, <i>Merveilles de
+l&rsquo;industrie</i>, volume 3, 1874, page 537.)</p>
+</div>
+
+<div class="figright" style="width: 300px;">
+<img src="images/i014.png" width="300" height="505" alt="Figure 6." title="Figure 6." />
+<p class="caption2">Figure 6.&mdash;<span class="smcap">An advertisement</span> with view of plant for
+manufacturing superphosphate about 1867. (From <span class="smcap">E. T. Freedley</span>,
+<i>Philadelphia and its Manufacturers in 1867</i>, page 288.)</p>
+</div></div>
+
+<div class="figcenter" style="width: 600px;">
+<span class="pagenum"><a name="Page_184" id="Page_184">[Pg 184]</a></span>
+<img src="images/i015.png" width="600" height="769" alt="Figure 7." title="Figure 7." />
+<p class="caption2">Figure 7.&mdash;<span class="smcap">Florida hard-rock phosphate mining.</span> (From
+Carroll D. Wright, <i>The Phosphate Industry of the United States</i>, sixth
+special report of the Commissioner of Labor, Government Printing Office,
+Washington, 1893, plate facing page 43.)</p>
+</div>
+
+<p>Graham had come to this understanding of the phosphoric acids through
+his previous studies of &ldquo;Alcoates, definite compounds of Salts and
+Alcohol analogous to the Hydrates&rdquo; (1831). Liebig started from analogies
+he saw with certain organic acids when he formulated the phosphoric
+acids with a constant proportion of water (aq.) and varying proportions
+of &ldquo;phosphoric acid&rdquo; (P) as follows:</p>
+
+<p style="margin-left:3em;"><span class="pagenum"><a name="Page_185" id="Page_185">[Pg 185]</a></span>2 P 3 aq.  phosphoric acid</p>
+<p style="margin-left:3em;">3 P 3 aq.  pyrophosphoric acid</p>
+<p style="margin-left:3em;">6 P 3 aq.  metaphosphoric acid.</p>
+
+<p>Salts are formed when a &ldquo;basis,&rdquo; i.e., a metal oxide, replaces water.
+When potassium-acid sulfate is neutralized by sodium base, the acid-salt
+divides into Glauber&rsquo;s salt and potassium sulfate, which proves the
+acid-salt to be a mixture of the neutral salt with its acid. Sodium-acid
+phosphate behaves quite differently. After neutralization by a potassium
+&ldquo;base&rdquo; (hydroxide), the salt does not split up; a uniform
+sodium-potassium phosphate is obtained. Therefore, phosphoric acid is
+truly three-basic!<a name="FNanchor_23_23" id="FNanchor_23_23"></a><a href="#Footnote_23_23" class="fnanchor">[23]</a>
+</p>
+
+<p>This result has later been confirmed, but the analogy by means of which
+it had been obtained was very weak, in certain parts quite wrong.</p>
+
+<p>The acids from the two lower oxides of phosphorus were also considered
+as three-basic. Adolphe Wurtz (1817-1884) formulated them in 1846,
+according to the theory of chemical types:</p>
+
+<p style="margin-left:4em;">(PO) &middot; &middot; &middot;<br />
+<span style="margin-left:5em;">O<sup>3</sup> &nbsp; &nbsp; phosphoric acid</span><br />
+<span style="margin-left:2em;">H<sup>3</sup></span></p>
+
+<p style="margin-left:4em;">(PHO) &middot; &middot;<br />
+<span style="margin-left:5em;">O<sup>2</sup> &nbsp; &nbsp; phosphorus acid</span><br />
+<span style="margin-left:2em;">H<sup>2</sup></span></p>
+
+<p style="margin-left:4em;">(PH<sup>2</sup>O) &middot;<br />
+<span style="margin-left:5em;">O &nbsp; &nbsp; &nbsp;hypophosphorous acid.<a name="FNanchor_24_24" id="FNanchor_24_24"></a><a href="#Footnote_24_24" class="fnanchor">[24]</a></span><br />
+<span style="margin-left:2em;">H</span></p>
+
+
+<p>Further proof for these constitutions was sought in the study of the
+esters formed when the acids react with alcohols.</p>
+
+<p>Among the analogies and generalizations by which the research on
+phosphoric acid was supported, and to the results of which it
+contributed a full share, was the new theory of acids. Not oxygen,
+Lavoisier&rsquo;s general acidifier, but reactive hydrogen determines the
+character of acids. In this brief survey, it seems sufficient just to
+mention this connection without describing it in detail.</p>
+
+<p>The study of phosphoric acids led to important new concepts in
+theoretical chemistry. The finding of polybasicity was extended to other
+acids and formed the model that helped to recognize the
+polyfunctionality in other compounds, like alcohols and amines. The
+hydrogen theory of acids was fundamental for further advance. In another
+dimension, it is particularly interesting to see that large-scale
+applications followed almost immediately and directly from the new
+theoretical insight. The first and foremost of these applications was in
+agriculture.</p>
+
+
+
+<hr style="width: 65%;" />
+<h3>Phosphates as Plant Nutrients</h3>
+
+
+<p>One hundred years after the discovery of &ldquo;cold light,&rdquo; the presence of
+phosphorus in plants and animals was ascertained, and its form was
+established as a compound of phosphoric acid. This knowledge had little
+practical effect until the &ldquo;nature&rdquo; of the acid, in its various forms,
+was explained through the work of Thomas Graham. From it, there started
+a considerable technical development.</p>
+
+<p>At about that time (1833), the Duke of Richmond proved that the
+fertilizing value of bones resided not in the gelatin, nor in the
+calcium, but in the phosphoric acid. Thus, he confirmed what Théodore de
+Saussure had said in 1804, that &ldquo;we have no reason to believe&rdquo; that
+plants can exist without phosphorus. Unknowingly at first, the farmer
+had supplied this element by means of the organic fertilizers he used:
+manure, excrements, bones, and horns. Now, with the value of phosphorus
+known, a search began for mineral phosphates to be applied as
+fertilizers. Jean Baptiste Boussingault (1802-1887), an agricultural
+chemist in Lyons, traveled to Peru to see the guano deposits. Garcilaso
+de la Vega (ca. 1540 to ca. 1616) noted in his history of Peru (1604)
+that guano was used by the Incas as a fertilizer. Two hundred years
+later, Alexander von Humboldt revived this knowledge, and Humphry Davy
+wrote about the benefits of guano to the soil. Yet, the application of
+this fertilizer developed only slowly, until Justus Liebig sang its
+praise. Imports into England rose and far exceeded those into France
+where, between 1857 and 1867, about 50,000 tons were annually received.</p>
+
+<p>The other great advance in the use of phosphatic plant nutrients started
+with Liebig&rsquo;s recommendation (1840) to treat bones with sulfuric acid
+for solubilization. This idea was not entirely new; since 1832, a
+production of a &ldquo;superphosphate&rdquo; from bones and sulfuric acid had been
+in progress at Prague. At<span class="pagenum"><a name="Page_186" id="Page_186">[Pg 186]</a></span> Rothamsted in 1842, John Bennet Lawes
+obtained a patent on the manufacture of superphosphate. Other
+manufactures in England followed and were successful, although James
+Muspratt (1793-1886) at Newton lost much time and &ldquo;some thousands of
+pounds&rdquo; on Liebig&rsquo;s idea of a &ldquo;mineral manure.&rdquo;</p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i018.png" width="600" height="361" alt="Figure 8." title="Figure 8." />
+<p class="caption">Figure 8.&mdash;<span class="smcap">Florida land-pebble phosphate mining.</span> (From
+Carroll D. Wright, <i>The Phosphate Industry of the United States ...</i>,
+plate facing page 58.)</p>
+</div>
+
+<p>It was difficult enough to establish the efficacy of bones and
+artificially produced phosphates in promoting the growth of plants under
+special conditions of soils and climate; therefore, the question as to
+the action of phosphates in the growing plant was not even seriously
+formulated at that time. The beneficial effects were obvious enough to
+increase the use of phosphates as plant nutrients and to call for new
+sources of supply. Active developments of phosphate mining and treating
+started in South Carolina in 1867, and in Florida in 1888.<a name="FNanchor_25_25" id="FNanchor_25_25"></a><a href="#Footnote_25_25" class="fnanchor">[25]</a></p>
+
+<p>In a reciprocal action, more phosphate application to soils stimulated
+increasing research on the conditions and reactions obtaining in the
+complex and varying compositions called soil. The findings of
+bacteriologists made it clear that physics and chemistry had to be
+amplified by biology for a real understanding of fertilizer effects.
+After 1900, for example, Julius Stoklasa (1857-1936) pointed out that
+bacterial action in soil solubilizes water-insoluble phosphates and
+makes them available to the plants.<a name="FNanchor_26_26" id="FNanchor_26_26"></a><a href="#Footnote_26_26" class="fnanchor">[26]</a></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i021.png" width="600" height="361" alt="Figure 9." title="Figure 9." />
+<p class="caption">Figure 9.&mdash;<span class="smcap">Florida river-pebble phosphate mining.</span> (From
+Carroll D. Wright, <i>The Phosphate Industry of the United States ...</i>,
+plate facing page 64.)</p>
+</div>
+
+<p>The insight into the importance of phosphorus in organisms, especially
+since Liebig&rsquo;s time, is reflected in the work of Friedrich Nietzsche
+(1844-1900). This &ldquo;re-valuator of all values&rdquo; who modestly said of
+himself: &ldquo;I am dynamite!&rdquo; once explained the human temperaments as
+caused by the inorganic salts they contain: <span class="pagenum"><a name="Page_187" id="Page_187">[Pg 187]</a></span>&ldquo;The differences in
+temperament are perhaps caused more by the different distribution and
+quantities of the inorganic salts than by everything else. Bilious
+people have too little sodium sulfate, the melancholics are lacking in
+potassium sulfate and phosphate; too little calcium phosphate in the
+phlegmatics. Courageous natures have an excess of iron phosphate.&rdquo; (See
+volume 12 of <i>Nietzsche&rsquo;s Works</i>, edit. Naumann-Kröner, Leipzig, 1886.)
+In this strange association of inorganic salts with human temperaments,
+the role of iron phosphate as a producer of courage is particularly
+interesting. What would a modern philosopher conclude if he followed the
+development of insight into the composition and function of complex
+phosphate compounds in organisms?</p>
+
+
+
+<hr style="width: 65%;" />
+<h3>From Inorganic to Organic Phosphates</h3>
+
+
+<p>By the middle of the 19th century, the source of phosphorus in natural
+phosphates and the chemistry of its oxidation products had been
+established. The main difficulty that had to be overcome was that these
+oxidation products existed in so many forms, not only several stages of
+oxidation, but, in addition, aggregations and condensations of the
+phosphoric acids. Once the fundamental chemistry of these acids was
+elucidated, the attention of chemists and physiologists turned to the
+task of finding the actual state in which phosphorus compounds were
+present in the organisms. It had been a great advance when it had been
+shown that plants need phosphates in their soil. This led to the next
+question concerning the materials in the body of the plant for which
+phosphates were being used and into which they were incorporated.
+Similarly, the knowledge that animals attain their phosphates from the
+digested plant food called, in the next step of scientific inquiry, for
+information on the nature of phosphates produced from this source.</p>
+
+<p>The method used in this inquiry was to subject anatomically separated
+parts of the organisms to chemical separations. The means for such
+separations had to be more gentle than the strong heat and destructive
+chemicals that had been considered adequate up to then. The
+interpretation of the new results naturally relied on the general
+advance of chemistry, the development of new methods for isolating
+substances of little stability, of new concepts concerning the
+arrangements of atoms in the molecules, and of new apparatus to measure
+their rates of change.<span class="pagenum"><a name="Page_188" id="Page_188">[Pg 188]</a></span></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i025.png" width="400" height="600" alt="T. PARKER.
+ELECTRICAL FURNACE.
+Patented Sept. 13, 1892.
+Fig. 1.
+
+Fig. 2.
+Inventor Thomas Parker
+By his attorneys Howson and Howson
+Witnesses: George Baumann John Revell" title="Figure 10." />
+<p class="caption2">Figure 10.&mdash;<span class="smcap">Electric furnace for producing elemental
+phosphorus</span>, invented by Thomas Parker of Newbridge, England, and
+assigned to The Electric Construction Corporation of the same place. The
+drawing is part of United States patent 482,586 (September 13, 1892).
+The furnace was patented in England on October 29, 1889 (no. 17,060); in
+France on June 23, 1890 (no. 206,566); in Germany on June 17, 1890 (no.
+55,700); and in Italy on October 23, 1890 (no. 431). The following
+explanation is cited from the U.S. patent:</p>
+<blockquote>
+<p>Figure 1 [shown here] is a vertical section of the furnace, and Fig. 2
+is a diagram to illustrate the means for regulating the electro-motive
+force or quantity of current across the furnace.</p>
+
+<p>F is the furnace containing the charge to be treated. It has an
+inlet-hopper at <i>a</i>, with slides AA, by which the charge can be admitted
+without opening communication between the interior of the furnace and
+the outer air.</p>
+
+<p>B is a screw conveyer by which the charge is pushed forward into the
+furnace.</p>
+
+<p><i>c´c´</i> are the electrodes, consisting of blocks or cylinders or the like
+of carbon fixed in metal socket-pieces <i>c c</i>, to which the
+electric-circuit wires <i>d</i> from the <a name="corr_40_2" id="corr_40_2"></a><ins class="mycorr" title="Original: dynano">dynamo</ins> D are affixed. The current,
+as aforesaid, may be either continuous or alternating. <i>c<sup>2</sup>c<sup>2</sup></i> are
+rods of metal or carbon, which are used to establish the electric
+circuit through the furnace, the said rods being inserted into holes in
+conductors <i>c<sup>3</sup></i> (in contact with the socket-pieces <i>c</i>) and in the
+furnace, as shown.</p>
+
+<p><i>g</i> is the outlet for the gas or vapor, <i>h</i> the slag-tap hole, and <i>x</i>
+the opening for manipulating the charge, the said openings being closed
+by clay or otherwise when the furnace is at work.</p>
+
+<p>I use coke or other form of carbon in the charge between the electrodes
+<i>c´</i>, the said coke being in contact with the said electrodes, so that
+complete incandescence is insured.</p>
+
+<p>A means for varying the electro-motive force or quantity of current
+across the furnace with the varying resistance of the charge is
+illustrated by the diagram, Fig. 2. <i>c´ c<sup>2</sup></i> indicate the electrodes
+in the furnace, as in Fig. 1, and D is the dynamo and T its terminals. E
+represents the exciting-circuit. R R are resistances, and R S is the
+resistance-switch, which is operated to put in more or less resistance
+at R as the resistance of the charge in the furnace lessens or
+increases. This switch may be automatically operated, and a suitable
+arrangement for the purpose is a current-regulator such as is described
+in the specification of English Letters Patent No. 14,504, of September
+14, 1889, granted to William Henry Douglas and Thomas Hugh Parker.</p>
+</blockquote></div>
+
+<p><span class="pagenum"><a name="Page_189" id="Page_189">[Pg 189]</a></span></p>
+
+<div class="figcenter" style="width: 650px;">
+
+<div class="figleft" style="width: 300px;">
+<img src="images/i026.png" width="300" height="330" alt="Fig 254.&mdash;Trempage &aacute; la presse.
+" title="Figure 11." />
+<p class="caption2">Figure 11.&mdash;<span class="smcap">Dipping of matchsticks</span> in France, about 1870.
+The frame which holds the matches so that one end protrudes at the
+bottom, is lowered over a pan containing molten sulfur. The
+sulfur-covered matches are then dropped into a phosphorous paste. See
+figure 12. (From <span class="smcap">Figuier</span>, <i>Merveilles de l&rsquo;industrie</i>, volume 3, 1874,
+page 575.)</p>
+</div>
+
+<div class="figright" style="width: 300px;">
+<img src="images/i027.png" width="300" height="329" alt="Fig. 256.&mdash;Coupe du plateau &aacute; tremper les
+allumettes chimiques dans la p&#226;te de phosphore &aacute; chaud et au bain-marie." title="Figure 12." />
+<p class="caption2">Figure 12.&mdash;<span class="smcap">Pan for dipping matchsticks</span> into phosphorus
+paste, about 1870. The letters on the picture are: A, matches; B, water
+bath; C, frame; D, plate; E, phosphorus paste; F, oven. The phosphorus
+paste of Böttger, 1842, contained 10 phosphorus, 25 antimony sulfide,
+12.5 manganese dioxide, 15 gelatin. According to Figuier (page 579), R.
+Wagner substituted lead dioxide for the manganese dioxide. (From
+<span class="smcap">Figuier</span>, volume 3, 1874, page 576.)</p>
+</div>
+</div>
+<p style="clear: both;">In the system of chemistry, as it developed in the first half of the
+19th century, the new development can be characterized as the turn from
+inorganic to organic phosphates, from the substance of minerals and
+strong chemical interactions to the components in which phosphate groups
+remained combined with carbon-containing substances.</p>
+
+
+
+<hr style="width: 65%;" />
+<h3>Phosphatides and Phosphagens</h3>
+
+
+<p>The important phosphorus compounds in organisms are much more complex
+than the simple salts, to which Nietzsche attributed such influence on
+man&rsquo;s character. Long before he wrote, it was known that phosphoric acid
+combines not only with inorganic bases to form salts, but with alcohols
+to form esters. In the middle of the 19th century, Théophile Juste
+Pelouze (1807-1867) extended this knowledge to an ester of glycerol.
+This proved to be significant in several respects. Glycerol had been
+shown by Michel Chevreul (1786-1889) as the substance in fats that is
+released in the process of soap boiling, when the fatty acids are
+converted into their salts. That it has the nature of an alcohol had
+been demonstrated by Marcellin Berthelot. Instead of one &ldquo;alcoholic&rdquo;
+hydroxyl group, OH, like ethanol (the alcohol of fermentation), or two
+hydroxyl groups (like ethylene glycol), glycerol contains three such
+groups. It was the only &ldquo;natural&rdquo; alcohol known at that time. That this
+alcohol would combine with phosphoric acid could be predicted, but that
+the ester, as obtained by Pelouze, still contained free acidic functions
+and formed a water-soluble barium salt was a new experience.</p>
+<p><span class="pagenum"><a name="Page_190" id="Page_190">[Pg 190]</a></span></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i028.png" width="400" height="785" alt="Alcoholic Fermentation" title="Figure 13." />
+<p class="caption2">Figure 13.&mdash;<span class="smcap">Survey of alcoholic fermentation</span>, 1951. The
+&ldquo;well-known scheme of alcoholic fermentation&rdquo; according to Albert Jan
+Kluyver (1888-1956), presented before the Society of Chemical Industry
+in the Royal Institution, March 7, 1951. In <i>Chemistry &amp; Industry</i>,
+1952, page 136 ff., Kluyver restates that &ldquo;... the fermentation of one
+molecule of glucose is indissolubly connected with the formation of two
+molecules of adenosine triphosphate (ATP) out of two molecules of
+adenosine diphosphate (ADP).&rdquo;</p>
+</div>
+
+<p style="clear:both;"><span class="pagenum"><a name="Page_191" id="Page_191">[Pg 191]</a></span>
+Shortly after this experience had been gained, it became valuable for
+understanding the chemical nature of a new substance extracted from a
+natural organ. This substance was named lecithin by its discoverer,
+Nicolas Théodore Gobley<a name="FNanchor_27_27" id="FNanchor_27_27"></a><a href="#Footnote_27_27" class="fnanchor">[27]</a> (1811-1876), because he obtained it from egg
+yolk (in Greek, <i>lékidos</i>). He used ether and alcohol for this
+extraction. Had he used water and mineral acid instead, he would not
+have found lecithin, but only its components. As Gobley and, slightly
+later, Oscar Liebreich (1839-1908), subjected lecithin to treatment with
+boiling water and acid, they separated it into three parts. One of them
+was the glycerophosphoric acid of Pelouze, the second was the well-known
+stearic acid of Chevreul, but the third was somewhat mysterious. This
+third substance was the same as one previously noticed when nerves had
+been subjected to an extraction by boiling water and acid and,
+therefore, called nerve-substance or neurine. Adolf Friedrich Strecker
+(1822-1871) established the identity of this neurine with a product he
+had extracted from bile and which went under the name of choline.
+Adolphe Wurtz (1817-1884) succeeded in synthesizing this substance from
+ethylene oxide, CH<sub>2</sub>.O.CH<sub>2</sub> and trimethylamine N(CH<sub>3</sub>)<sub>3</sub>.<a name="FNanchor_28_28" id="FNanchor_28_28"></a><a href="#Footnote_28_28" class="fnanchor">[28]</a> Thus, all
+three parts were identified, and Strecker put them together to construct
+a chemical formula for lecithin, glycerophosphoric acid combined with a
+fatty acid and with choline (a hydrate of neurine).</p>
+
+<table id="lecithin" summary="Structure of lecithin according to Strecker">
+<tr><td></td><td rowspan="3" style="font-size: 3em; vertical-align:top;">{</td><td>OH</td><td rowspan="3" style="font-size: 3em; vertical-align:top;">}</td><td>&nbsp;</td></tr>
+<tr><td>N</td> <td>(CH<sub>3</sub>)<sub>3</sub></td> <td>Choline</td></tr>
+<tr><td> </td> <td>C<sub>2</sub>H<sub>4</sub>O</td> <td></td></tr>
+<tr><td>&nbsp;</td></tr>
+</table>
+<table id="lecithin2" summary="Structure of lecithin according to Strecker">
+<tr><td>C<sub>18</sub>H<sub>33</sub>O<sub>2</sub></td><td rowspan="3" style="font-size: 3em; vertical-align:top;">}</td><td style="text-align: right;">HO</td><td rowspan="3" style="font-size: 3em; vertical-align:top;">}</td></tr>
+<tr><td></td><td></td><td>PO</td></tr>
+<tr><td>C<sub>16</sub>H<sub>31</sub>O<sub>2</sub></td><td style="text-align: right;">C<sub>3</sub>H<sub>5</sub>O</td></tr>
+<tr><td>Fatty Acids</td><td></td><td colspan="4">Glycerophosphate</td></tr>
+<tr><td style="text-align: center;" colspan="5">'&mdash;&mdash;&mdash;&mdash;&mdash;<sub>v</sub>&mdash;&mdash;&mdash;&mdash;'</td></tr>
+<tr><td style="text-align: center;" colspan="5">Lecithin</td></tr>
+<tr><td style="text-align: center;" colspan="5">according to Strecker</td></tr>
+</table>
+
+<p>This formula was not quite correct. Richard Willstätter showed that an
+internal neutralization takes place between the amino group and the free
+acidic residue. This is expressed in his lecithin formula of 1918.</p>
+
+<div class="figcenter" style="width: 300px;">
+<img src="images/lecithin_1918.png" width="300" height="178" alt="Lecithin (1918)" title="" />
+<p class="caption">Lecithin (1918)</p>
+</div>
+
+<p>When the aim was to distill elementary phosphorus out of an organic
+material, it did not matter whether this was fresh or putrified. For
+obtaining lecithin out of egg yolk and similar materials, it was
+essential to use it in fresh condition. Otherwise, enzymes would have
+decomposed it. Through more recent work, four enzymes have been
+separated, which act specifically in decomposing lecithin. Enzyme A
+removes one fatty acid and leaves a complex residue, called
+lysolecithin, intact. Enzyme B attacks this residue and splits off the
+remaining fatty acid group from it, enzyme C liberates only the choline
+from lecithin, and enzyme D opens lecithin at the ester bond between
+glycerol and phosphoric acid. This is shown in the following diagram.</p>
+
+<table id="lecithin3" summary="Enzymatic Splitting of Lecithins">
+<tr><th colspan="3"><span class="smcap">Enzymatic Splitting of Lecithins</span></th></tr>
+<tr><td><span class="smcap">Enzyme</span></td><td><span class="smcap">Substrate</span></td><td><span class="smcap">Products</span></td></tr>
+<tr><td style="text-align:center;">A</td><td>Lecithin</td><td>Lysolecithin and fatty acids.</td></tr>
+<tr><td style="text-align:center;">B</td><td>Lysolecithin</td><td>Glycero-phospho-choline and fatty acids.</td></tr>
+<tr><td style="text-align:center;">C</td><td>Lecithin</td><td>Phosphatidic acid and choline.</td></tr>
+<tr><td style="text-align:center;">D</td><td>Lecithin</td><td>Phosphoryl choline and diglyceride.</td></tr>
+</table>
+
+<p>Several fatty acids can be present in lecithin from various sources:
+palmitic and oleic acid, besides the stearic acid which at first had
+been thought the only one involved. In another group of extracts from
+brain or nerve tissue, amino-ethanol H<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>OH is found
+instead of the choline of lecithin. The variations include the alcohol,
+to which the fatty acids and choline phosphate are attached, <a name="corr_40_3" id="corr_40_3"></a><ins class="mycorr" title="Original: For">for</ins>
+example, glycerol can be replaced by the so-called meat-sugar, inositol,
+which has six hydroxyl groups in its hexagon-shaped molecule
+<span class="pagenum"><a name="Page_192" id="Page_192">[Pg 192]</a></span>C<sub>6</sub>H<sub>6</sub>(OH)<sub>6</sub>.</p>
+
+<div class="figleft" style="width: 300px;">
+<img src="images/i032.png" width="300" height="401" alt="Figure 14." title="figure 14." />
+<p class="caption2">Figure 14.&mdash;<span class="smcap">Eduard Buchner</span> (1860-1917) received the Nobel
+Prize in Chemistry for his discovery of cell-free fermentation, the
+first step in finding the role of phosphate in fermentations (1907).</p>
+</div>
+
+<p>The generally similar behavior of these phosphate-and fat-containing
+substances was emphasized by Ludwig Thudichum (1829-1901). He coined the
+name phosphatides for this group of substances from seeds and
+nerves.<a name="FNanchor_29_29" id="FNanchor_29_29"></a><a href="#Footnote_29_29" class="fnanchor">[29]</a> His work on the phosphates in brain substance aroused
+particular interest. When William Crookes drew his highly imaginative
+picture of an &ldquo;evolution&rdquo; of the chemical elements, he put into it
+&ldquo;phosphorus for the brain, salt for the sea, clay for the solid
+earth....&rdquo;<a name="FNanchor_30_30" id="FNanchor_30_30"></a><a href="#Footnote_30_30" class="fnanchor">[30]</a> But <a name="corr_40_4" id="corr_40_4"></a>
+<ins class="mycorr" title="Original: phosphatide soccur">phosphatides occur</ins> in many places of organisms, in
+bacteria, in leaves and roots of plants, in fat and tissues of animals.
+And where phosphatides are found, there are also enzymes that
+specifically act on them. They are called phosphatases to imply that
+they split the phosphatides. In addition, enzymes are present, which
+transfer phosphate groups from one compound to another. They are more
+abundant in seeds of high fat content than in the more starch-containing
+seeds, but even potatoes and orange juice have phosphatases.<a name="FNanchor_31_31" id="FNanchor_31_31"></a><a href="#Footnote_31_31" class="fnanchor">[31]</a></p>
+
+<p>Thus, from phosphatides, phosphoric acid is generated, and they could
+also be called phosphagens. Since 1926, however, the name phosphagens
+has been reserved for a group of organic substances that release their
+phosphoric acid very readily. The link between phosphorus and carbon is
+provided by oxygen in the phosphatides, by nitrogen in the phosphagens.
+In vertebrates, the basis for the phosphoric acid is creatine, whereas
+invertebrates have arginine instead.</p>
+
+<div class="figcenter" style="width: 350px;">
+<div class="figleft" style="width: 150px;">
+<img src="images/creatine_phosphate.png" width="150" height="152" alt="Creatine Phosphate" title="" />
+<span class="caption">Creatine Phosphate</span>
+</div>
+<div class="figright" style="width: 150px;">
+<img src="images/arginine_phosphate.png" width="150" height="279" alt="Arginine Phosphate" title="" />
+<span class="caption">Arginine phosphate</span>
+</div>
+</div>
+
+<hr style="width: 65%;" />
+<h3>Nuclein and Nucleic Acids</h3>
+
+
+<p>All parts of an organism are essential for life. Only with this in mind
+does it make sense to say that the most important part of the cell is
+its nucleus. From the nuclei of cells in pus and in salmon sperm, Johann
+Friedrich Miescher (1811-1887) obtained a peculiar kind of substance,
+which he named nuclein (1868). Its phosphate content was easily
+discovered, but to find the exact proportions and the nature of the
+other components required special methods of separation from
+phosphatides and other proteins. It was difficult to develop such
+methods at a time when little was known about the properties, and
+particularly<span class="pagenum"><a name="Page_193" id="Page_193">[Pg 193]</a></span> the stability, of a nuclein. For preparing nuclein from
+yeast cells, Felix Hoppe-Seyler (1825-1895) described the following
+details: Yeast is dispersed in water to extract soluble materials, like
+salts or sugars. After a few hours, the insoluble material is separated,
+washed once more with water, and then extracted with a very dilute
+solution of sodium hydroxide. The slightly alkaline solution, freed from
+insoluble residues, is slowly added to a weak hydrochloric acid. A
+precipitate forms which is separated by filtration, washed with dilute
+acid, then with cold alcohol, and finally extracted by boiling alcohol.
+The dried residue is the nuclein.<a name="FNanchor_32_32" id="FNanchor_32_32"></a><a href="#Footnote_32_32" class="fnanchor">[32]</a> It contains six percent
+phosphorus. A little more washing with water, a slightly longer
+treatment with acid or alcohol gives products of lower phosphorus
+content. Many experimental variations were necessary to establish the
+procedure that leads to purification without alteration of the natural
+substance.</p>
+
+<p>This was also true for the methods of chemical degradation, carried out
+in order to find the components of nucleins in their highest state of
+natural complexity. It was learned for example, that the special kind of
+carbohydrate present in nucleins was very susceptible to change under
+the conditions of hydrolysis by acids. Phoebus Aaron Theodor Levine
+(1869-1940), therefore, used the digestion by a living organism. With E.
+S. London, he introduced a solution of nucleic acid into, e.g., the
+gastrointestinal segment of a dog through a gastric fistula and withdrew
+the product of digestion through an intestinal fistula. Fortunately, the
+products obtained in such degradations were not new in themselves. The
+carbohydrate in this nucleic acid proved to be identical with D-ribose,
+which Emil Fischer had artificially made from arabinose and named ribose
+to indicate this relationship (1891). The nitrogenous products of the
+degradation were identical with substances previously prepared in the
+long study of uric acid. In the course of this study, Emil Fischer
+established uric acid and a number of its derivatives as having the
+elementary skeleton of what he called &ldquo;pure uric acid,&rdquo; abbreviated to
+purine. Out of Adolf Baeyer&rsquo;s work on barbituric acid came the knowledge
+of pyrimidine and its derivatives.</p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i035a.png" width="300" height="331" alt="Figure 15." title="Figure 15." />
+<p class="caption2">Figure 15.&mdash;<span class="smcap">Albrecht Kossel</span> (1853-1927) received the
+Nobel Prize in Medicine and Physiology in 1910 for his work on nucleic
+substances, which contain a high proportion of phosphorus. The chemical
+bonds of this phosphorus in the molecules of nucleic substances were
+determined in later work. (<i>Photo courtesy National Library of Medicine,
+Washington, D.C.</i>)</p>
+</div>
+
+<p>From these findings, together with what Oswald Schmiedeberg (1838-1921)
+had established concerning the presence of four phosphate groups in the
+molecule (1899), Robert Feulgen (1884-1955) constructed the following
+scheme of a nucleic acid. Feulgen&rsquo;s formula of 1918 is:</p>
+<div style="margin-left:4em;">
+<p>Phosphoric acid&mdash;Carbohydrate&mdash;Guanine</p>
+<p>Phosphoric acid&mdash;Carbohydrate&mdash;Cytosine</p>
+<p>Phosphoric acid&mdash;Carbohydrate&mdash;Thymine</p>
+<p>Phosphoric acid&mdash;Carbohydrate&mdash;Adenine</p>
+</div>
+
+<p>Of the four basic components on the right, thymine occurs in the
+<a name="corr_40_5" id="corr_40_5"></a><ins class="mycorr" title="Original: nucleidic">nucleic</ins>
+acid from the thymus gland. Yeast contains uracil instead. The
+difference between these two bases is one methyl group: thymine is a
+5-methyluracil. In all of these basic substances, the structure of urea</p>
+
+<pre>
+      NH<sub>2</sub>
+     /
+    C=O
+     \
+      NH<sub>2</sub>
+</pre>
+
+<p>is involved, and they form pairs of oxidized and reduced states:
+<span class="pagenum"><a name="Page_194" id="Page_194">[Pg 194]</a></span></p>
+
+<table id="purine" summary="Purine &amp; Pyrimidine">
+<tr><td><span class="smcap">Purine</span></td><td style="text-align: right;"><span class="smcap">Pyrimidine</span></td></tr>
+<tr><td style="text-align: right;">(reduced) Adenine</td><td> + </td><td>(oxidized) Thymine</td></tr>
+<tr><td style="text-align: right;">(oxidized) Guanine</td><td> +  </td><td>(reduced) Cytosine</td></tr>
+</table>
+
+<div class="figcenter" style="width: 300px;">
+<img src="images/pyrimidine.png" width="188" height="149" alt="Pyrimidine" title="" />
+<p class="caption">Pyrimidine</p>
+</div>
+
+<div class="figcenter" style="width: 550px;">
+<div class="figleft" style="width: 249px;">
+<img src="images/purine.png" width="249" height="226" alt="Purine" title="" />
+<p class="caption">Purine</p>
+</div>
+<div class="figright" style="width: 220px;">
+<img src="images/adenine.png" width="220" height="203" alt="Adenine" title="" />
+<p class="caption">Adenine</p>
+</div>
+</div>
+<p style="clear:both;">&nbsp;</p>
+
+<div class="figcenter" style="width: 680px;">
+<div class="figleft" style="width: 248px;">
+<img src="images/guanine.png" width="248" height="223" alt="Guanine" title="" />
+<p class="caption">Guanine</p>
+</div>
+<div class="figright" style="width: 161px;">
+<img src="images/uracil.png" width="161" height="198" alt="Uracil" title="" />
+<p class="caption">Uracil</p>
+</div>
+</div>
+<div><img src="images/cytosine.png" width="210" height="201" alt="Cytosine" title="" /></div>
+<p class="caption">Cytosine</p>
+
+<p style="clear:both;" class="center">The carbohydrate is ribose or deoxyribose.</p>
+
+<div class="figcenter" style="width: 400px;">
+<div class="figleft" style="width: 179px;">
+<img src="images/arabinose.png" width="179" height="239" alt="Arabinose" title="" />
+<p class="caption">Arabinose</p>
+</div>
+<div class="figright" style="width: 166px;">
+<img src="images/l-ribose.png" width="166" height="232" alt="L-Ribose" title="" />
+<p class="caption"><span class="smcap">l</span>-Ribose</p>
+</div>
+</div>
+<p style="clear:both;" class="center">Fischer and Piloty, 1891</p>
+
+<div class="figcenter" style="width: 415px;">
+<img src="images/deoxyribose.png" width="415" height="145" alt="Deoxyribose" title="" />
+<p class="caption">Deoxyribose</p>
+</div>
+
+<p>The exact position of phosphoric acid was established after long work
+and verified by synthesis.<a name="FNanchor_33_33" id="FNanchor_33_33"></a><a href="#Footnote_33_33" class="fnanchor">[33]</a></p>
+
+<p>A compound of adenine, ribose, and phosphoric acid was found in yeast,
+blood, and in skeletal muscle of mammals. From 100 grams of such muscle,
+0.35-0.40 grams of this compound were isolated. If the muscle is at
+rest, the compound contains three molecules of phosphoric acid, linked
+through oxygen atoms. It was named adenosine triphosphate or
+adenyltriphosphoric acid,<a name="FNanchor_34_34" id="FNanchor_34_34"></a><a href="#Footnote_34_34" class="fnanchor">[34]</a> usually abbreviated by the symbol ATP. It
+releases one phosphoric acid group very easily and goes over in the
+diphosphate, ADP, but it can also lose 2 P-groups as pyrophosphoric acid
+and leave the monophosphate, AMP.</p>
+
+<div class="figcenter" style="width: 400px;">
+<img src="images/i037.png" width="400" height="206" alt="Adenosine Triphosphate: Adenine, D-Ribose, Phosphoric
+acid" title="" />
+</div>
+
+<p>This change of ATP was considered to be the main source of energy in
+muscle contraction by Otto Meyerhof.<a name="FNanchor_35_35" id="FNanchor_35_35"></a><a href="#Footnote_35_35" class="fnanchor">[35]</a> The corresponding derivatives
+of guanine, cytosine, and uracil were also found, and they are active in
+the temporary transfer of phosphoric acid groups in biological
+processes.</p>
+
+<p>Thus, the study of organic phosphates progressed from the comparatively
+simple esters connected with fatty substances of organisms to the
+proteins and the nuclear substances of the cell. The proportional amount
+of phosphorus in the former was larger than in the latter; the actual
+importance and function in the life of organisms, however, is not
+measured by the quantity but determined by the special nature of the
+compounds.<span class="pagenum"><a name="Page_195" id="Page_195">[Pg 195]</a></span></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i038.png" width="300" height="268" alt="Figure 16." title="Figure 16." />
+<p class="caption2">Figure 16.&mdash;<span class="smcap">Otto Meyerhof</span> (1884-1951) received one-half
+of the Nobel Prize in Medicine and Physiology in 1922 for his discovery
+of the metabolism of lactic acid in muscle, which involves the action of
+phosphates, especially adenosine duophosphates. (<i>Photo courtesy
+National Library of Medicine, Washington, D.C.</i>)</p>
+</div>
+
+<div class="figcenter" style="width: 660px;">
+<div class="figleft" style="width: 300px;">
+<img src="images/i039a.png" width="300" height="359" alt="Figure 17." title="Figure 17." />
+</div>
+<div class="figright" style="width: 300px;">
+<img src="images/i039b.png" width="300" height="358" alt="Figure 17." title="Figure 17." />
+</div>
+<div class="figcenter" style="width: 600px; clear:both;">
+<p class="caption2">Figure 17.&mdash;<span class="smcap">Arthur Harden</span> (1865-1940), left, <span class="smcap">and Hans A.
+S. von Euler-Chelpin</span> (b. 1875), right, shared the Nobel Prize in
+Chemistry in 1929. Harden received it for his research in fermentation,
+which showed the influence of phosphate, particularly the formation of a
+hexose diphosphate. Euler-Chelpin received his award for his research in
+fermentation. He found coenzyme A which is a nucleotide containing
+phosphoric acid.</p>
+</div>
+</div>
+
+<p><span class="pagenum"><a name="Page_196" id="Page_196">[Pg 196]</a></span></p>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i040.png" width="300" height="413" alt="Figure 18." title="Figure 18." />
+<p class="caption2">Figure 18.&mdash;<span class="smcap">George de Hevesy</span> (b. 1885) received the Nobel
+Prize in Chemistry in 1943 for his research with isotopic tracer
+elements, particularly radiophosphorus of weight 32 (ordinary phosphorus
+is 31).</p>
+</div>
+
+<div class="figcenter" style="width: 650px;">
+<div class="figleft" style="width: 300px;">
+<img src="images/i041a.png" width="300" height="400" alt="Figure 19." title="Figure 19." />
+</div>
+<div class="figright" style="width: 285px;">
+<img src="images/i041b.png" width="285" height="400" alt="Figure 19." title="Figure 19." />
+</div>
+<div class="figcenter" style="width: 600px; clear:both;">
+<p class="caption2">Figure 19.&mdash;<span class="smcap">Carl F. Cori</span> (b. 1896) <span class="smcap">and his wife, Gerty T.
+Cori</span> (1896-1957) received part of the Nobel Prize in Medicine and
+Physiology in 1947 for their study on glycogen conversion. In the course
+of this study, they identified glucose 1-phosphate, now usually referred
+to as &ldquo;Cori ester,&rdquo; and its function in the glycogen cycle. (<i>Photo
+courtesy National Library of Medicine, Washington, D.C.</i>)</p>
+</div>
+</div>
+
+<p><span class="pagenum"><a name="Page_197" id="Page_197">[Pg 197]</a></span>
+The study of this function is the newest phase in the history of
+phosphorus and represents the culmination of the previous efforts. This
+newest phase developed out of an accidental discovery concerning one of
+the oldest organic-chemical industries, the production of alcohol by the
+fermentative action of yeast on sugar. A transition of carbohydrates
+through phosphate compounds to the end products of the fermentation
+process was found, and it gradually proved to be a kind of model for a
+host of biological processes.</p>
+
+<p>Specific phosphates were thus found to be indispensable for life. In
+reverse, the wrong kind of phosphates can destroy life. As a result, an
+important part of the new phase in phosphorus history consisted in the
+study&mdash;and use&mdash;of antibiotic phosphorus compounds.</p>
+
+
+
+<hr style="width: 65%;" />
+<h3>Phosphates in Biological Processes</h3>
+
+
+<p>The first indication that phosphorus is important for life came from the
+experience that plants take it up from the substances in the soil. They
+incorporate it in their body substance. What makes phosphorus so
+important that they cannot grow without it? The next insight was that
+animals acquire it from their plant food. It is then found in bones, in
+fat and nerve tissue, in all cells and particularly in the cell nuclei.
+What are its functions there?</p>
+
+<p>The answers to such questions were developed from the study of a
+long-known process, the conversion of carbohydrates into carbon dioxide
+and alcohol by yeast. It started with Eduard Buchner&rsquo;s discovery of
+1890, that fermentation is produced by a preparation from yeast in which
+all living cells have been removed. When yeast is dead-ground and
+pressed out, the juice still has the ability to produce fermentation.</p>
+
+<p>It is strange, but in many ways characteristic for the process of
+science, that the &ldquo;riddle&rdquo; of phosphorus in life was solved by first
+eliminating life. In such &ldquo;lifeless&rdquo; fermentations, Arthur Harden found
+that the conversion of sugar begins with the formation of a hexose
+phosphate (1904). The &ldquo;ferment&rdquo; of yeast, called zymase, proved to be a
+composite of several enzymes. Hans von Euler-Chelpin isolated one part
+of zymase, which remains active even after heating its solution to the
+boiling point. From 1 kilogram of yeast, he obtained 20 milligrams of
+this heat-stable enzyme, which he called cozymase and identified as a
+nucleotide composed of a purine, a sugar, and phosphoric acid.<a name="FNanchor_36_36" id="FNanchor_36_36"></a><a href="#Footnote_36_36" class="fnanchor">[36]</a> In
+the years between the two World Wars, zymase was further resolved into
+more enzymes, one of them the coenzyme I, which was shown to be ADP
+connected with another molecule of ribose attached to the amide of
+nicotinic acid, or diphosphopyridine nucleotide:</p>
+
+<div class="figcenter" style="width: 400px;">
+<img src="images/i043b.png" width="400" height="355" alt="Coenzyme I" title="" />
+</div>
+
+
+<div class="figcenter" style="width: 650px;">
+<div class="figleft" style="width: 300px;">
+<img src="images/i043a.png" width="300" height="382" alt="Figure 20." title="Figure 20." />
+<p class="caption2">Figure 20.&mdash;<span class="smcap">Fritz A. Lipmann</span> (b. 1899) shared with Hans
+Adolf Krebs the Nobel Prize in Medicine and Physiology in 1953 for his
+work on coenzyme A. He discovered acetyl phosphate as the substance in
+bacteria, which transfers phosphate to adenylic acid.</p>
+</div>
+<p><span class="pagenum"><a name="Page_198" id="Page_198">[Pg 198]</a></span></p>
+<div class="figright" style="width: 300px;">
+<img src="images/i044.png" width="300" height="419" alt="Figure 21." title="Figure 21." />
+<p class="caption2">Figure 21.&mdash;<span class="smcap">Alexander R. Todd</span> (b. 1907) received the
+Nobel Prize in Chemistry in 1957 for his research on nucleotides. He
+determined the position of the phosphate groups in the molecule and
+confirmed it by synthesis of dinucleotide phosphates.</p>
+</div>
+</div>
+
+<p style="clear:both;">Its function is connected with the transfer of hydrogen between
+intermediates formed through phosphate-transferring enzymes.
+Fermentation proceeds by a cascade of processes, in which phosphate
+groups swing back and forth, and equilibria between ATP with ADP play a
+major role.</p>
+
+<p>Many of the enzymes are closely related to vitamins. Thus, cocarboxylase
+A, which takes part in the separation of carbon dioxide from an
+intermediate fermentation product, is the phosphate of vitamin B<sub>1</sub>.
+Others of the B vitamins contain phosphate groups, for example those of
+the B<sub>2</sub> and B<sub>6</sub> group, and in B<sub>12</sub>, one lonely phosphate forms a
+bridge in the large molecule that contains one atom of cobalt:
+C<sub>63</sub>H<sub>90</sub>N<sub>14</sub>O<sub>14</sub>PCo. The formation of vitamin A from carotine
+occurs under the influence of ATP.</p>
+
+<p>The first stages in fermentation are like those in respiration, which
+ends with carbon dioxide and water. These two are the materials for the
+reverse process in photosynthesis. When light is absorbed by the
+chlorophyll of green plants, one of the initial reactions is a transfer
+of hydrogen from water to a triphosphopyridine nucleotide, which later
+acts to reduce the carbon dioxide. Under the influence of ATP,
+phosphoglyceric acid is synthesized and further built up by way of
+carbohydrate phosphates to hexose sugars and finally to starch. In many
+starchy fruits, a small proportion of phosphate remains attached to the
+end product.</p>
+
+<p>The synthesis of proteins is under the control of deoxyribonucleic acid
+or ribonucleic acid, abbreviated by the symbols DNA and RNA. The genes
+in the nucleus are parts of a giant DNA molecule. RNA is a universal
+constituent of all living cells. Where protein synthesis is intense, the
+content in RNA is high. Thus, the spinning glands of silkworms are
+extraordinarily rich in RNA.<a name="FNanchor_37_37" id="FNanchor_37_37"></a><a href="#Footnote_37_37" class="fnanchor">[37]</a></p>
+
+<p>In his research on the radioactive isotope P<sup>32</sup>, George de Hevesy gained
+some insight into the surprising mobility of phosphates in organisms: &ldquo;A
+phosphate radical taken up with the food may first participate in the
+phosphorylation of glucose in the intestinal mucose, soon afterwards
+pass into the circulation as free phosphate, enter a red corpuscle,
+become incorporated with an adenosine triphosphoric-acid molecule,
+participate in a glycolytic process going on in the corpuscle, return to
+circulation, penetrate into the liver cells, participate in the
+formation of a phosphatide molecule, after a short interval enter the
+circulation in this form, penetrate into the spleen, and leave this
+organ after some time as a constituent of a lymphocyte. We may meet the
+phosphate radical again as a constituent of the plasma, from which it
+may find its way into the skeleton.&rdquo;<a name="FNanchor_38_38" id="FNanchor_38_38"></a><a href="#Footnote_38_38" class="fnanchor">[38]</a> Much has been added in the last
+30 years to complete this picture in many details and to extend it to
+other biochemical processes, including even the changes of the pigments
+in the retina in the visual process, or in the conversion of chemical
+energy to light by bacteria and insects.</p>
+
+
+
+<hr style="width: 65%;" />
+<h3>Medicines and Poisons</h3>
+
+
+<p>In the delicate balance of these processes, disturbances may occur which
+can be remedied by specific phosphate-containing medicines. Thus,
+adenosine phosphate has been recommended in cases of angina<span class="pagenum"><a name="Page_199" id="Page_199">[Pg 199]</a></span> pectoris
+and marketed under trade names like sarkolyt, or in compounds named
+angiolysine. A considerable number of physiologically active organic
+phosphates can be found in the patent literature.<a name="FNanchor_39_39" id="FNanchor_39_39"></a><a href="#Footnote_39_39" class="fnanchor">[39]</a> Yeast itself is
+considered to be a valuable food additive.</p>
+
+<p>On the other hand, there are phosphate compounds that act as poisons.
+One group of such compounds was discovered in 1929 by W. Lange, who
+wrote: &ldquo;Of interest is the strong action of mono-fluorophosphate esters
+on the human body&mdash;the effect is produced by very small quantities.&rdquo;<a name="FNanchor_40_40" id="FNanchor_40_40"></a><a href="#Footnote_40_40" class="fnanchor">[40]</a>
+Diisopropyl fluorophosphate has since become a potential agent for
+chemical warfare. It inactivates an enzyme which controls the
+transmission of nerve impulses to muscle, <a name="corr_40_6" id="corr_40_6"></a><ins class="mycorr" title="Original: acetylcholin">acetylcholine</ins> esterase.</p>
+
+<p>Organic esters of phosphoric acids are used as insecticides. The
+hexa-ethylester of tetraphosphoric acid, prepared by Gerhard Schrader by
+heating triethylphosphate with phosphorus oxychloride,<a name="FNanchor_41_41" id="FNanchor_41_41"></a><a href="#Footnote_41_41" class="fnanchor">[41]</a> actually
+contains tetraethylpyrophosphate (TEPP) among others. Bayer&rsquo;s Dipterex,
+the dimethyl ester of 2,2,2-trichloro-1-hydroxyethyl-phosphonate, has
+been modified to dimethyl-2,2-dichlorovinyl-phosphate and is especially
+active against the oriental fruit fly.<a name="FNanchor_42_42" id="FNanchor_42_42"></a><a href="#Footnote_42_42" class="fnanchor">[42]</a></p>
+
+<div class="figleft">
+<span class="pagenum"><a name="Page_200" id="Page_200">[Pg 200]</a></span>
+<img src="images/dipterex.png" width="250" height="149" alt="Bayer's L 13/59 (Dipterex)" title="" />
+</div>
+<p><br /><br />Bayer's L 13/59<br />(Dipterex)</p>
+<p style="clear:both;">&nbsp;</p>
+<div class="figleft">
+<img src="images/schradan.png" width="300" height="159" alt="Octamethylpyrophosphoramide: Schradan" title="" />
+</div>
+<p><br /><br />Schradan<br />Octamethylpyrophosphoramide</p>
+
+<div class="figcenter" style="width: 650px; clear:both;">
+<div class="figleft" style="width: 300px;">
+<img src="images/i048a.png" width="300" height="381" alt="Figure 22." title="Figure 22." />
+</div>
+<div class="figright" style="width: 303px;">
+<img src="images/i048b.png" width="303" height="381" alt="Figure 22." title="Figure 22." />
+</div>
+<div class="figcenter" style="width: 600px; clear:both;">
+<p class="caption2">Figure 22.&mdash;<span class="smcap">Arthur Kornberg</span> (b. 1918) <span class="smcap">and Severo Ochoa</span>
+(b. 1905) shared the Nobel Prize in Medicine and Physiology in 1959.
+Kornberg received it for research on the biological synthesis of
+deoxyribonucleic acid. In particular, he found that four triphosphate
+components and a small amount of the end product as a &ldquo;template&rdquo; had to
+be present for the enzymatic synthesis. Ochoa received his share of the
+prize for research in ribonucleic acid and deoxyribonucleic acid. In
+particular, Ochoa synthesized polyribonucleotides and used the
+radioactive isotope, P<sup>32</sup>. The synthetic polyribonucleotides were
+found to resemble the natural substances in all essentials.</p>
+</div>
+</div>
+
+<div class="figcenter" style="width: 600px;">
+<img src="images/i049a.png" width="300" height="328" alt="Figure 23." title="Figure 23." />
+<p class="caption2">Figure 23.&mdash;<span class="smcap">Melvin Calvin</span> (b. 1911) received the Nobel
+Prize in Chemistry in 1961 for his research in photosynthesis, in which
+he specified the function of phosphoglyceric acid as an intermediate in
+the synthesis of carbohydrates from carbon dioxide and water by green
+plants.</p>
+</div>
+
+<p>The story of phosphorus, which began 300 years ago, has acquired new
+importance in this century. Many scientists have contributed to it: 13
+of them have received Nobel Prizes for work directly bearing on the
+chemical and biological importance of phosphorus compounds. In
+chronological order, they are: Eduard Buchner, Albrecht Kossel, Otto
+Meyerhof, Arthur Harden, Hans von Euler-Chelpin, George de <a name="corr_40_7" id="corr_40_7"></a><ins class="mycorr" title="Comma inserted">Hevesy,</ins> Carl
+F. Cori, Gerty T. Cori, Fritz Lipmann, Lord Alexander Todd, Arthur
+Kornberg, Severo Ochoa, and Melvin Calvin. The developers of industrial
+production and commercial utilization of phosphate compounds have had
+other rewards.</p>
+
+<p>Some impression of the continuing growth in this field<a name="FNanchor_43_43" id="FNanchor_43_43"></a><a href="#Footnote_43_43" class="fnanchor">[43]</a> can be gained
+from the following data.</p>
+
+<p class="center"><span class="smcap">Phosphate Rock</span><br />
+annually &ldquo;sold or used by producer&rdquo; in the United States in million long
+tons (2,240 lbs.)</p>
+
+<table id="table1" summary="Year, Million Long Tons">
+<tr><td>    1880&nbsp; &nbsp; &nbsp;</td><td>    0.2</td></tr>
+<tr><td>    1890</td><td>    0.5</td></tr>
+<tr><td>    1900</td><td>    1.5</td></tr>
+<tr><td>    1910</td><td>    2.655</td></tr>
+<tr><td>    1920</td><td>    4.104</td></tr>
+<tr><td>    1930</td><td>    3.926</td></tr>
+<tr><td>    1940</td><td>    4.003</td></tr>
+<tr><td>    1945</td><td>    5.807</td></tr>
+<tr><td>    1950</td><td>   11.114</td></tr>
+<tr><td>    1955</td><td>   12.265</td></tr>
+<tr><td>    1955</td><td>   (world: about 56)</td></tr>
+<tr><td>    1960</td><td>   17.202</td></tr>
+<tr><td>    1962</td><td>   19.060</td></tr>
+</table>
+
+<p class="center">Sources: U.S. Bureau of the Census. <i>Historical Statistics of the United
+States 1789-1945</i> (1949); <i>Statistical Abstract of the United States.</i></p>
+
+<p class="center"><span class="smcap">Elemental Phosphorus</span><br />
+annually produced in the United States in short tons (2,000 lbs.)</p>
+
+<table id="table2" summary="Year, Short Tons">
+<tr><td>1939&nbsp; &nbsp; &nbsp;</td><td>43,000</td></tr>
+<tr><td>1944</td><td>85,679</td></tr>
+<tr><td>1950</td><td>153,233</td></tr>
+<tr><td>1956</td><td>312,200</td></tr>
+<tr><td>1958</td><td>335,750</td></tr>
+<tr><td>1959</td><td>366,350</td></tr>
+<tr><td>1960</td><td>409,096</td></tr>
+<tr><td>1961</td><td>430,617</td></tr>
+<tr><td>1962</td><td>451,970</td></tr>
+</table>
+
+<p class="center">Source: U.S. Department of Commerce.</p>
+
+
+
+<hr style="width: 65%;" />
+<div class="footnotes">
+<h3>FOOTNOTES:</h3>
+
+<div class="footnote"><p><a name="Footnote_1_1" id="Footnote_1_1"></a><a href="#FNanchor_1_1"><span class="label">[1]</span></a> <span class="smcap">Wilhelm Homberg</span>, <i>Mémoires Académie, 1666-1699</i> (Paris,
+1730), vol. 10, under date of April 30, 1692, pp. 57-61.</p></div>
+
+<div class="footnote"><p><a name="Footnote_2_2" id="Footnote_2_2"></a><a href="#FNanchor_2_2"><span class="label">[2]</span></a> <span class="smcap">Fortunio Licetus</span>, <i>Lithiophosphorus sive de lapide
+Bononiensi</i> (Venice, 1640).</p></div>
+
+<div class="footnote"><p><a name="Footnote_3_3" id="Footnote_3_3"></a><a href="#FNanchor_3_3"><span class="label">[3]</span></a> Cited in <span class="smcap">Peter Joseph Macquer</span> <i>Chymisches Wörterbuch</i>, 2nd
+ed. (Leipzig: Weidmann, 1789), vol. 4, p. 508, footnote &ldquo;c&rdquo; as &ldquo;Kletwich
+(de phosph. liqu. et solid. 1689, Thes. II).&rdquo;</p></div>
+
+<div class="footnote"><p><a name="Footnote_4_4" id="Footnote_4_4"></a><a href="#FNanchor_4_4"><span class="label">[4]</span></a> <span class="smcap">Ferdinand Hoefer</span>, <i>Histoire de la Chimie</i> (Paris, 1843),
+vol. 1, p. 339.</p></div>
+
+<div class="footnote"><p><a name="Footnote_5_5" id="Footnote_5_5"></a><a href="#FNanchor_5_5"><span class="label">[5]</span></a> <span class="smcap">G. W. von Leibniz</span>, <i>Mémoires Académie</i> (Paris, 1682);
+<i>Akademie der Wissenschaften, Miscellanea Berolinensia</i> (Berlin, 1710),
+vol. 1, p. 91.</p></div>
+
+<div class="footnote"><p><a name="Footnote_6_6" id="Footnote_6_6"></a><a href="#FNanchor_6_6"><span class="label">[6]</span></a> <span class="smcap">Jean Hellot</span>, <i>Mémoires Académie 1737</i> (Paris, 1766), under
+date of November 13, 1737, pp. 342-378.</p></div>
+
+<div class="footnote"><p><a name="Footnote_7_7" id="Footnote_7_7"></a><a href="#FNanchor_7_7"><span class="label">[7]</span></a> <span class="smcap">Macquer</span>, op. cit. (footnote 3), p. 551.</p></div>
+
+<div class="footnote"><p><a name="Footnote_8_8" id="Footnote_8_8"></a><a href="#FNanchor_8_8"><span class="label">[8]</span></a> <span class="smcap">A. S. Marggraf</span>, <i>Akademie der Wissenschaften, Miscellanea
+Berolinensia</i> (Berlin, 1743), vol. 7, 342 ff.; see also <span class="smcap">Wilhelm Ostwald</span>
+<i>Klassiker der Exakten Naturwissenschaften</i> (Leipzig: Engelmann, 1913),
+no. 187.</p></div>
+
+<div class="footnote"><p><a name="Footnote_9_9" id="Footnote_9_9"></a><a href="#FNanchor_9_9"><span class="label">[9]</span></a> <span class="smcap">G. Hanckewitz</span>, [Hankwitz], <i>Philosophical Transactions of
+the Royal Society of London</i>, 1724-1734, abridged (London, 1809), vol.
+7, pp. 596-602.</p></div>
+
+<div class="footnote"><p><a name="Footnote_10_10" id="Footnote_10_10"></a><a href="#FNanchor_10_10"><span class="label">[10]</span></a> <span class="smcap">Antoine Laurent Lavoisier</span>, &ldquo;Sur la Combustion du Phosphore
+de Kunckel, Et sur la nature de l&rsquo;acide qui resulte de cette
+Combustion,&rdquo; <i>Mémoires Académie 1777</i>, (Paris, 1780), pp. 65-78.</p></div>
+
+<div class="footnote"><p><a name="Footnote_11_11" id="Footnote_11_11"></a><a href="#FNanchor_11_11"><span class="label">[11]</span></a> <span class="smcap">Guyton de Morveau</span> and others, <i>Méthode de Nomenclature
+Chimique</i>, Proposée par MM. de Morveau, Lavoisier, Bertholet, &amp; de
+Fourcroy (Paris, 1787), plate 9.</p></div>
+
+<div class="footnote"><p><a name="Footnote_12_12" id="Footnote_12_12"></a><a href="#FNanchor_12_12"><span class="label">[12]</span></a> <span class="smcap">Macquer</span>, op. cit. (footnote 3), p. 513.</p></div>
+
+<div class="footnote"><p><a name="Footnote_13_13" id="Footnote_13_13"></a><a href="#FNanchor_13_13"><span class="label">[13]</span></a> <span class="smcap">Marie Boas</span>, <i>Robert Boyle and Seventeenth Century
+Chemistry</i> (New York: Cambridge University Press, 1958), p. 226; see
+also <span class="smcap">Wyndham Miles</span>, &ldquo;The History of Dr. Brand&rsquo;s Phosphorus Elementarus,&rdquo;
+<i>Armed Forces Chemical Journal</i> (November-December 1958), p. 25.</p></div>
+
+<div class="footnote"><p><a name="Footnote_14_14" id="Footnote_14_14"></a><a href="#FNanchor_14_14"><span class="label">[14]</span></a> <span class="smcap">Archibald Clow</span> and <span class="smcap">Nan L. Clow</span>, <i>The Chemical Revolution</i>
+(London: Batchworth Press, 1952), p. 451.</p></div>
+
+<div class="footnote"><p><a name="Footnote_15_15" id="Footnote_15_15"></a><a href="#FNanchor_15_15"><span class="label">[15]</span></a> <span class="smcap">Émile Kopp</span>, <i>Comptes-rendus hebdomadaires des Séances de
+l&rsquo;Académie des Sciences, Paris</i> (1844), vol. 18, p. 871; <span class="smcap">Wilhelm
+Hittorf</span>, <i>Annalen der Chemie und Pharmazie</i>, suppl. to vol. 4, p. 37;
+<span class="smcap">Anton Schrötter</span>, <i>Annales de Chimie et de Physique</i>, series 3, vol. 24
+(1848), p. 406; see also Schrötter&rsquo;s report on &ldquo;Phosphor und Zündwaaren&rdquo;
+in <span class="smcap">A. W. von Hofmann</span>, <i>Bericht über die Entwicklung der Chemischen
+Industrie</i> (Braunschweig: Vieweg, 1875), pp. 219-246.</p></div>
+
+<div class="footnote"><p><a name="Footnote_16_16" id="Footnote_16_16"></a><a href="#FNanchor_16_16"><span class="label">[16]</span></a> <span class="smcap">R. Glauber</span>, <i>Furni Novi Philosphici</i> (Amsterdam, 1649),
+vol. 2, pp. 12 ff.</p></div>
+
+<div class="footnote"><p><a name="Footnote_17_17" id="Footnote_17_17"></a><a href="#FNanchor_17_17"><span class="label">[17]</span></a> <span class="smcap">Hermann Schelenz</span>, <i>Geschichte der Pharmazie</i> (Berlin:
+Springer, 1904), p. 598.</p></div>
+
+<div class="footnote"><p><a name="Footnote_18_18" id="Footnote_18_18"></a><a href="#FNanchor_18_18"><span class="label">[18]</span></a> <span class="smcap">J. Personne</span>, <i>Comptes-rendus ...</i>, Paris (1869), vol. 68,
+pp. 543-546.</p></div>
+
+<div class="footnote"><p><a name="Footnote_19_19" id="Footnote_19_19"></a><a href="#FNanchor_19_19"><span class="label">[19]</span></a> <span class="smcap">A. Wurtz</span>, <i>Dictionnaire de Chimie</i> (Paris, 1876), vol. 2,
+part 2, p. 951.</p></div>
+
+<div class="footnote"><p><a name="Footnote_20_20" id="Footnote_20_20"></a><a href="#FNanchor_20_20"><span class="label">[20]</span></a> <span class="smcap">Karl W. Scheele</span>, <i>Nachgelassene Briefe und
+Aufzeichnungen</i>, edit. A. E. Nordenskiöld (Stockholm: Norstedt, 1892),
+pp. 38, 144.</p></div>
+
+<div class="footnote"><p><a name="Footnote_21_21" id="Footnote_21_21"></a><a href="#FNanchor_21_21"><span class="label">[21]</span></a> <span class="smcap">J. J. Berzelius</span>, <i>Lehrbuch</i>, transl. F. Wöhler (Dresden,
+1827), vol. 3, part 1, p. 96.</p></div>
+
+<div class="footnote"><p><a name="Footnote_22_22" id="Footnote_22_22"></a><a href="#FNanchor_22_22"><span class="label">[22]</span></a> <span class="smcap">Thomas Graham</span>, <i>Philosophical Transactions of the Royal
+Society of London</i> (1833), pp. 253-284.</p></div>
+
+<div class="footnote"><p><a name="Footnote_23_23" id="Footnote_23_23"></a><a href="#FNanchor_23_23"><span class="label">[23]</span></a> <span class="smcap">Justus Liebig&rsquo;s</span> <i>Annalen der Pharmacie</i> (1838), vol. 26,
+p. 113 ff.</p></div>
+
+<div class="footnote"><p><a name="Footnote_24_24" id="Footnote_24_24"></a><a href="#FNanchor_24_24"><span class="label">[24]</span></a> <span class="smcap">A. Wurtz</span>, <i>Annales de Chimie et de Physique</i>, series 3,
+vol. 16 (1846), p. 190.</p></div>
+
+<div class="footnote"><p><a name="Footnote_25_25" id="Footnote_25_25"></a><a href="#FNanchor_25_25"><span class="label">[25]</span></a> <span class="smcap">Carroll D. Wright</span>, <i>The Phosphate Industry in the United
+States</i>, sixth special report of the Commissioner of Labor (Washington,
+1893).</p></div>
+
+<div class="footnote"><p><a name="Footnote_26_26" id="Footnote_26_26"></a><a href="#FNanchor_26_26"><span class="label">[26]</span></a> <span class="smcap">J. Stoklasa</span>, <i>Biochemischer Kreislauf des Phosphat-Ions im
+Boden, Centralblatt für Bakteriologie ...</i> (Jena: Fischer, March 22,
+1911), vol. 29, nos. 15-19.</p></div>
+
+<div class="footnote"><p><a name="Footnote_27_27" id="Footnote_27_27"></a><a href="#FNanchor_27_27"><span class="label">[27]</span></a> <span class="smcap">N. T. Gobley</span>, <i>Comptes-rendus</i> ..., Paris (1845), vol. 21,
+p. 718.</p></div>
+
+<div class="footnote"><p><a name="Footnote_28_28" id="Footnote_28_28"></a><a href="#FNanchor_28_28"><span class="label">[28]</span></a> <span class="smcap">A. Wurtz</span>, <i>Comptes-rendus</i> ..., Paris (1868), vol. 66, p.
+772.</p></div>
+
+<div class="footnote"><p><a name="Footnote_29_29" id="Footnote_29_29"></a><a href="#FNanchor_29_29"><span class="label">[29]</span></a> <span class="smcap">L. Thudichum</span>, <i>Die chemische Constitution des Gehirns des
+Menschen und der Tiere</i> (1901); see also <span class="smcap">H. Wittcoff</span>, <span class="smcap">The Phosphatides</span>
+(New York: Reinhold, 1951).</p></div>
+
+<div class="footnote"><p><a name="Footnote_30_30" id="Footnote_30_30"></a><a href="#FNanchor_30_30"><span class="label">[30]</span></a> <span class="smcap">William Crookes</span>, <i>British Association for the Advancement
+of Science, Reports</i> (1887), sec. B, p. 573.</p></div>
+
+<div class="footnote"><p><a name="Footnote_31_31" id="Footnote_31_31"></a><a href="#FNanchor_31_31"><span class="label">[31]</span></a> <span class="smcap">J. E. Courtois</span> and <span class="smcap">A. Lino</span>, <i>Progress in the Chemistry of
+Organic Natural Products</i>, edit. L. Zechmeister (Vienna: Springer
+Verlag, 1961), vol. 19, p. 316-373.</p></div>
+
+<div class="footnote"><p><a name="Footnote_32_32" id="Footnote_32_32"></a><a href="#FNanchor_32_32"><span class="label">[32]</span></a> <span class="smcap">A. Wurt</span>, <i>Dictionnaire de Chimie</i>, supp. part 2, [n.d.] p.
+1087; <span class="smcap">A. Kossel</span>, <i>Zeitschrift für physiologische Chemie</i>, series 3
+(1879), p. 284.</p></div>
+
+<div class="footnote"><p><a name="Footnote_33_33" id="Footnote_33_33"></a><a href="#FNanchor_33_33"><span class="label">[33]</span></a> <span class="smcap">Alexander Todd</span>, <i>Les Prix Nobel en 1957</i> (Stockholm).</p></div>
+
+<div class="footnote"><p><a name="Footnote_34_34" id="Footnote_34_34"></a><a href="#FNanchor_34_34"><span class="label">[34]</span></a> <span class="smcap">Hans von Euler-Chelpin</span>, <i>Les Prix Nobel en 1929</i>
+(Stockholm).</p></div>
+
+<div class="footnote"><p><a name="Footnote_35_35" id="Footnote_35_35"></a><a href="#FNanchor_35_35"><span class="label">[35]</span></a> <span class="smcap">O. Meyerhof</span> and <span class="smcap">E. Lundsgaard</span>, <i>Naturwissenschaften</i>
+(Berlin, 1930), vol. 18, pp. 330, 787.</p></div>
+
+<div class="footnote"><p><a name="Footnote_36_36" id="Footnote_36_36"></a><a href="#FNanchor_36_36"><span class="label">[36]</span></a> <span class="smcap">K. Lohmann</span>, <i>Naturwissenschaften</i> (Berlin, 1929), vol. 17,
+p. 624; <span class="smcap">C. H. Fiske</span> and <span class="smcap">Y. Subbarow</span>, <i>Science</i> (Washington, 1929), vol.
+70, p. 381 f.</p></div>
+
+<div class="footnote"><p><a name="Footnote_37_37" id="Footnote_37_37"></a><a href="#FNanchor_37_37"><span class="label">[37]</span></a> <span class="smcap">J. Brachet</span>, <i>Scientia, Revista di Scienza</i> (1960), vol.
+95, p. 119.</p></div>
+
+<div class="footnote"><p><a name="Footnote_38_38" id="Footnote_38_38"></a><a href="#FNanchor_38_38"><span class="label">[38]</span></a> <span class="smcap">George de Hevesy</span>, <i>Les Prix Nobel en 1940</i> (Stockholm).
+See also <span class="smcap">Eduard Farber</span>, <i>Nobel Prize Winners in Chemistry</i>, 2nd ed. (New
+York: Schuman, 1963), p. 179.</p></div>
+
+<div class="footnote"><p><a name="Footnote_39_39" id="Footnote_39_39"></a><a href="#FNanchor_39_39"><span class="label">[39]</span></a> <a name="corr_40_8" id="corr_40_8"></a><ins class="mycorr" title="Original: See.">See,</ins> e.g., <i>Chemical Week</i>, vol. 77 (September 3, 1955),
+p. 79 f.; <span class="smcap">J. Bolle</span>, <i>Chimie et Industrie</i> (1960), vol. 83, p. 252.</p></div>
+
+<div class="footnote"><p><a name="Footnote_40_40" id="Footnote_40_40"></a><a href="#FNanchor_40_40"><span class="label">[40]</span></a> <span class="smcap">W. Lange</span>, <i>Berichte der Deutschen Chemischen Gesellschaft</i>
+(Berlin, 1929), vol. 62, p. 793; vol. 65 (1932), p. 1598.</p></div>
+
+<div class="footnote"><p><a name="Footnote_41_41" id="Footnote_41_41"></a><a href="#FNanchor_41_41"><span class="label">[41]</span></a> <span class="smcap">Gerhard Schrader</span>, U.S. patent 2,336,302 of 1943 (priority
+in Germany, 1938); <span class="smcap">S. A. Hall</span> and <span class="smcap">M. Jacobson</span>, <i>Industrial and
+Engineering Chemistry</i> (1943), vol. 40, p. 694.</p></div>
+
+<div class="footnote"><p><a name="Footnote_42_42" id="Footnote_42_42"></a><a href="#FNanchor_42_42"><span class="label">[42]</span></a> <span class="smcap">A. M. Mattsen</span> and others, <i>Journal of Agriculture and Food
+Chemistry</i> (1955), vol. 3, p. 319.</p></div>
+
+<div class="footnote"><p><a name="Footnote_43_43" id="Footnote_43_43"></a><a href="#FNanchor_43_43"><span class="label">[43]</span></a> <span class="smcap">John B. Van Wazer</span>, <cite>Phosphorus and its Compounds</cite>, 2 vols.
+(vol. 1, <cite>Chemistry</cite>; vol. 2 <cite>Technology, Biological Functions and
+Applications</cite>), New York: Interscience, 1958, 1961.</p></div>
+</div>
+
+<hr style="width: 25%;" />
+
+<p class="center"><small>U.S. GOVERNMENT PRINTING OFFICE: 1965</small></p>
+
+<p class="center"><small>For sale by the Superintendent of Documents, U.S. Government Printing
+Office Washington, D.C. 20402&mdash;Price 25 cents</small></p>
+
+
+<hr style="width: 65%;" />
+
+<h3>INDEX</h3>
+
+<p>Aristotle, <a href="#Page_179">179</a><br /><br /></p>
+
+
+<p>Baeyer, Adolf, <a href="#Page_193">193</a></p>
+
+<p>Bechil, Achild, <a href="#Page_179">179</a></p>
+
+<p>Berthelot, Marcellin, <a href="#Page_189">189</a></p>
+
+<p>Berzelius, Jöns Jakob, <a href="#Page_182">182</a></p>
+
+<p>Black and Bell, plant at Stratford, <a href="#Page_182">182</a></p>
+
+<p>Boussingault, Jean Baptiste, <a href="#Page_185">185</a></p>
+
+<p>Boyle, Robert, <a href="#Page_178">178</a>, <a href="#Page_179">179</a></p>
+
+<p>Brand, H., <a href="#Page_178">178</a>, <a href="#Page_179">179</a></p>
+
+<p>Buchner, Hans, <a href="#Page_197">197</a>, <a href="#Page_200">200</a><br /><br /></p>
+
+
+<p>Calvin, Melvin, <a href="#Page_200">200</a></p>
+
+<p>Casciarolo, Vicenzo, <a href="#Page_179">179</a></p>
+
+<p>Chevreul, Michel, <a href="#Page_189">189</a></p>
+
+<p>Cori, Carl F., <a href="#Page_200">200</a></p>
+
+<p>Cori, Gerti T., <a href="#Page_200">200</a></p>
+
+<p>Crookes, William, <a href="#Page_192">192</a><br /><br /></p>
+
+
+<p>Davy, Sir Humphry, <a href="#Page_185">185</a></p>
+
+<p>De Hevesy, George, <a href="#Page_198">198</a>, <a href="#Page_200">200</a></p>
+
+<p>De la Vega, Garcilaso, <a href="#Page_185">185</a></p>
+
+<p>De Saussure, Théodore, <a href="#Page_185">185</a><br /><br /></p>
+
+
+<p>Euler-Chelpin, Hans von, <a href="#Page_197">197</a>, <a href="#Page_200">200</a><br /><br /></p>
+
+
+<p>Fernelius, Jean, <a href="#Page_179">179</a></p>
+
+<p>Feulgen, Robert, <a href="#Page_193">193</a></p>
+
+<p>Fischer, Emil, <a href="#Page_193">193</a><br /><br /></p>
+
+
+<p><a name="corr_40_9" id="corr_40_9"></a><ins class="mycorr" title="Original: G&auml;hn">Gahn</ins>, Johann Gottlieb, <a href="#Page_182">182</a></p>
+
+<p>Gay-Lussac, Joseph Louis, <a href="#Page_182">182</a></p>
+
+<p>Gobley, Nicolas Théodore, <a href="#Page_191">191</a></p>
+
+<p>Graham, Thomas, <a href="#Page_182">182</a>, <a href="#Page_183">183</a>, <a href="#Page_185">185</a><br /><br /></p>
+
+
+<p>Hankwitz, Gottfried, <a href="#Page_180">180</a></p>
+
+<p>Harden, Arthur, <a href="#Page_197">197</a>, <a href="#Page_200">200</a></p>
+
+<p>Hartmann, Immanuel Peter, <a href="#Page_181">181</a></p>
+
+<p>Hellot, Jean, <a href="#Page_180">180</a></p>
+
+<p>Henry II, King of France, <a href="#Page_179">179</a></p>
+
+<p>Hittorf, Wilhelm, <a href="#Page_181">181</a></p>
+
+<p>Hoefer, Ferdinand, <a href="#Page_179">179</a></p>
+
+<p>Holmberg, Wilhelm, <a href="#Page_178">178</a></p>
+
+<p>Hoppe-Seyler, Felix, <a href="#Page_193">193</a></p>
+
+<p>Humboldt, Alexander von, <a href="#Page_185">185</a></p>
+
+<p>Huygens, Christiaan, <a href="#Page_179">179</a><br /><br /></p>
+
+
+<p>Incas, <a href="#Page_185">185</a><br /><br /></p>
+
+
+<p>Kletwich, Johann Christopher, <a href="#Page_179">179</a></p>
+
+<p>Koppe, Émile, <a href="#Page_181">181</a></p>
+
+<p>Kornberg, Arthur, <a href="#Page_200">200</a></p>
+
+<p>Kossel, Albrecht, <a href="#Page_200">200</a></p>
+
+<p>Kraft, Johann Daniel, <a href="#Page_179">179</a></p>
+
+<p>Kramer, Dr. &mdash;&mdash;, <a href="#Page_181">181</a></p>
+
+<p>Kunckel, Johann, <a href="#Page_179">179</a><br /><br /></p>
+
+
+<p>Lange, W., <a href="#Page_199">199</a></p>
+
+<p>Lavoisier, Antoine Laurent, <a href="#Page_181">181</a>, <a href="#Page_185">185</a></p>
+
+<p>Laws, John Bennet, <a href="#Page_186">186</a></p>
+
+<p>Leibnitz, Gottfried Wilhelm von, <a href="#Page_179">179</a></p>
+
+<p>Lennox, Charles, third Duke of Richmond, <a href="#Page_185">185</a></p>
+
+<p>Leonhardi, Johann Gottfried, <a href="#Page_179">179</a></p>
+
+<p>Levine, Phoebus Aaron Theodor, <a href="#Page_193">193</a></p>
+
+<p>Liebig, Justus, <a href="#Page_183">183</a>, <a href="#Page_185">185</a>, <a href="#Page_186">186</a></p>
+
+<p>Liebreich, Oscar, <a href="#Page_191">191</a></p>
+
+<p>Lipmann, Fritz, <a href="#Page_200">200</a></p>
+
+<p>London, E. S., <a href="#Page_193">193</a><br /><br /></p>
+
+
+<p>Macquer, Peter Joseph, <a href="#Page_180">180</a></p>
+
+<p>Marggraf, Andreas Sigismund, <a href="#Page_180">180</a></p>
+
+<p>Meyerhof, Otto, <a href="#Page_194">194</a>, <a href="#Page_200">200</a></p>
+
+<p>Miescher, Johann Friedrich, <a href="#Page_192">192</a></p>
+
+<p>Muspratt, James, <a href="#Page_186">186</a><br /><br /></p>
+
+
+<p>Nietzsche, Friedrich, <a href="#Page_186">186</a>, <a href="#Page_187">187</a>, <a href="#Page_189">189</a><br /><br /></p>
+
+
+<p>Ochoa, Severo, <a href="#Page_200">200</a><br /><br /></p>
+
+
+<p>Pelouze, Théophile Juste, <a href="#Page_189">189</a><br /><br /></p>
+
+
+<p>Rouelle, Guillaume François, <a href="#Page_181">181</a><br /><br /></p>
+
+
+<p>Scheele, Karl W., <a href="#Page_182">182</a></p>
+
+<p>Schmiedeberg, Oswald, <a href="#Page_193">193</a></p>
+
+<p>Schrader, Gerhard, <a href="#Page_199">199</a></p>
+
+<p>Schrötter, Anton, <a href="#Page_181">181</a></p>
+
+<p>Stoklasa, Julius, <a href="#Page_186">186</a></p>
+
+<p>Strecker, Adolf Friedrich, <a href="#Page_191">191</a><br /><br /></p>
+
+
+<p>Thudichum, Ludwig, <a href="#Page_192">192</a></p>
+
+<p>Todd, Lord Alexander, <a href="#Page_200">200</a><br /><br /></p>
+
+
+<p>Willm, Edmond, <a href="#Page_182">182</a></p>
+
+<p>Willstätter, Richard, <a href="#Page_191">191</a></p>
+
+<p>Wurtz, Adolphe, <a href="#Page_185">185</a>, <a href="#Page_191">191</a><br /><br /></p>
+
+
+<div class="tnote">
+<h3><a name="corrections_37" id="corrections_37"></a>Transcriber&rsquo;s Notes</h3>
+
+
+<p>The following typographical errors have been corrected:</p>
+
+<p class="hang4">Page <a href="#corr_40_1">180</a> &ldquo;<i>Abfällen</i>, Vieweg, Braunschweig,&rdquo; - had &ldquo;Viewig&rdquo;.</p>
+
+<p class="hang4">Page <a href="#corr_40_2">188</a> &ldquo;wires <i>d</i> from the dynamo D&rdquo; - had &ldquo;dynano&rdquo;.</p>
+
+<p class="hang4">Page <a href="#corr_40_3">191</a> &ldquo;phosphate are attached, for example,&rdquo; - had &ldquo;attached, For&rdquo;.</p>
+
+<p class="hang4">Page <a href="#corr_40_4">192</a> &ldquo;But phosphatides occur&rdquo; - had &ldquo;phosphatide soccur&rdquo;.</p>
+
+<p class="hang4">Page <a href="#corr_40_5">193</a> &ldquo;the nucleic acid from the thymus&rdquo; - had &ldquo;nucleidic&rdquo;.</p>
+
+<p class="hang4">Page <a href="#corr_40_6">199</a> &ldquo;acetylcholine esterase.&rdquo; - had &ldquo;acetylcholin&rdquo;.</p>
+
+<p class="hang4">Page <a href="#corr_40_7">200</a> &ldquo;George de Hevesy, Carl F. Cori,&rdquo; - comma added after Hevesy.</p>
+
+<p class="hang4">Footnote <a href="#corr_40_8">39</a>: &ldquo;See, e.g., <i>Chemical Week</i>, vol. 77&rdquo; - had &ldquo;See. e.g.&rdquo;</p>
+
+<p class="hang4"><a href="#corr_40_9">Index Entry</a>: &ldquo;Gahn, Johann Gottlieb, 182&rdquo; - had &ldquo;Gähn&rdquo;</p>
+
+<p>The spelling of &ldquo;Bertholet&rdquo; [Claude Louis Berthollet] is as given on the
+original title page of the work referenced in this paper.</p>
+
+<p>Inconsistent hyphenation of chemical names has been retained.</p>
+</div>
+
+
+
+
+
+
+
+
+<pre>
+
+
+
+
+
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+</body>
+</html>
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+The Project Gutenberg EBook of History of Phosphorus, by Eduard Farber
+
+This eBook is for the use of anyone anywhere at no cost and with
+almost no restrictions whatsoever.  You may copy it, give it away or
+re-use it under the terms of the Project Gutenberg License included
+with this eBook or online at www.gutenberg.org
+
+
+Title: History of Phosphorus
+
+Author: Eduard Farber
+
+Release Date: September 20, 2010 [EBook #33766]
+
+Language: English
+
+Character set encoding: ASCII
+
+*** START OF THIS PROJECT GUTENBERG EBOOK HISTORY OF PHOSPHORUS ***
+
+
+
+
+Produced by Chris Curnow, Joseph Cooper, Louise Pattison
+and the Online Distributed Proofreading Team at
+https://www.pgdp.net
+
+
+
+
+
+
+
+
+
+Transcriber's Note.
+
+This is Paper 40 from the Smithsonian Institution United States National
+Museum Bulletin 240, comprising Papers 34-44, which will also be
+available as a complete e-book.
+
+The front material, introduction and relevant index entries from the
+Bulletin are included in each single-paper e-book.
+
+Corrections are listed at the end of the e-book.
+
+
+
+
+SMITHSONIAN INSTITUTION
+
+UNITED STATES NATIONAL MUSEUM
+
+BULLETIN 240
+
+
+[Illustration]
+
+SMITHSONIAN PRESS
+
+
+MUSEUM OF HISTORY AND TECHNOLOGY
+
+CONTRIBUTIONS FROM THE MUSEUM OF HISTORY AND TECHNOLOGY
+
+  _Papers 34-44_
+  _On Science and Technology_
+
+SMITHSONIAN INSTITUTION . WASHINGTON, D.C. 1966
+
+
+
+
+_Publications of the United States National Museum_
+
+
+The scholarly and scientific publications of the United States National
+Museum include two series, _Proceedings of the United States National
+Museum_ and _United States National Museum Bulletin_.
+
+In these series, the Museum publishes original articles and monographs
+dealing with the collections and work of its constituent museums--The
+Museum of Natural History and the Museum of History and
+Technology--setting forth newly acquired facts in the fields of
+anthropology, biology, history, geology, and technology. Copies of each
+publication are distributed to libraries, to cultural and scientific
+organizations, and to specialists and others interested in the different
+subjects.
+
+The _Proceedings_, begun in 1878, are intended for the publication, in
+separate form, of shorter papers from the Museum of Natural History.
+These are gathered in volumes, octavo in size, with the publication date
+of each paper recorded in the table of contents of the volume.
+
+In the _Bulletin_ series, the first of which was issued in 1875, appear
+longer, separate publications consisting of monographs (occasionally in
+several parts) and volumes in which are collected works on related
+subjects. _Bulletins_ are either octavo or quarto in size, depending on
+the needs of the presentation. Since 1902 papers relating to the
+botanical collections of the Museum of Natural History have been
+published in the _Bulletin_ series under the heading _Contributions from
+the United States National Herbarium_, and since 1959, in _Bulletins_
+titled "Contributions from the Museum of History and Technology," have
+been gathered shorter papers relating to the collections and research of
+that Museum.
+
+The present collection of Contributions, Papers 34-44, comprises
+Bulletin 240. Each of these papers has been previously published in
+separate form. The year of publication is shown on the last page of each
+paper.
+
+FRANK A. TAYLOR _Director, United States National Museum_
+
+
+
+
+    CONTRIBUTIONS FROM
+    THE MUSEUM OF HISTORY AND TECHNOLOGY:
+    PAPER 40
+
+
+
+
+    HISTORY OF PHOSPHORUS
+
+    _Eduard Farber_
+
+
+
+
+          THE ELEMENT FROM ANIMALS AND PLANTS      178
+
+                                   EARLY USES      181
+
+    CHEMICAL CONSTITUTION OF PHOSPHORIC ACIDS      182
+
+                PHOSPHATES AS PLANT NUTRIENTS      185
+
+         FROM INORGANIC TO ORGANIC PHOSPHATES      187
+
+                 PHOSPHATIDES AND PHOSPHAGENS      189
+
+                    NUCLEIN AND NUCLEIC ACIDS      192
+
+           PHOSPHATES IN BIOLOGICAL PROCESSES      197
+
+                        MEDICINES AND POISONS      198
+
+
+
+
+_Eduard Farber_
+
+
+
+
+HISTORY OF PHOSPHORUS
+
+
+     _The "cold light" produced by phosphorus caused it to be
+     considered a miraculous chemical for a long time after its
+     discovery, about 1669. During the intervening three centuries
+     numerous other chemical miracles have been found, yet
+     phosphorus retains a special aura of universal importance in
+     chemistry. Many investigators have occupied themselves with
+     this element and its diverse chemical compounds. Further
+     enlightenment and insight into the ways of nature can be
+     expected from these efforts._
+
+     _Not only is the story of phosphorus a major drama in the
+     history of chemistry; it also illustrates, in a spectacular
+     example, the growth of this science through the discovery of
+     connections between apparently unrelated phenomena, and the
+     continuous interplay between basic science and the search for
+     practical usage._
+
+     THE AUTHOR: _Eduard Farber is a research professor at American
+     University, Washington, D.C., and has been associated with the
+     Smithsonian Institution as a consultant in chemistry._
+
+
+When phosphorus was discovered, nearly three centuries ago, it was
+considered a miraculous thing. The only event that provoked a similar
+emotion was the discovery of radium more than two centuries later. The
+excitement about the _Phosphorus igneus_, Boyle's _Icy Noctiluca_, was
+slowly replaced by, or converted into, chemical research. Yet, if we
+would allow room for emotion in research, we could still be excited
+about the wondrous substance that chemical and biological work continues
+to reveal as vitally important. It is a fundamental plant nutrient, an
+essential part in nerve and brain substance, a decisive factor in muscle
+action and cell growth, and also a component in fast-acting, powerful
+poisons. The importance of phosphorus was gradually recognized and the
+means by which this took place are characteristic and similar to other
+developments in the history of science. This paper was written in order
+to summarize these various means which led to the highly complex ways of
+present research.
+
+
+
+
+The Element from Animals and Plants
+
+
+It was a little late to search for the philosophers' stone in 1669, yet
+it was in such a search that phosphorus was discovered. Wilhelm Homberg
+(1652-1715) described it in the following manner: Brand, "a man little
+known, of low birth, with a bizarre and mysterious nature in all he
+did, found this luminous matter while searching for something else. He
+was a glassmaker by profession, but he had abandoned it in order to be
+free for the pursuit of the philosophical stone with which he was
+engrossed. Having put it into his mind that the secret of the
+philosophical stone consisted in the preparation of urine, this man
+worked in all kinds of manners and for a very long time without finding
+anything. Finally, in the year 1669, after a strong distillation of
+urine, he found in the recipient a luminant matter that has since been
+called phosphorus. He showed it to some of his friends, among them
+Mister Kunkel [sic]."[1]
+
+Neither the name nor the phenomenon were really new. Organic
+phosphorescent materials were known to Aristotle, and a lithophosphorus
+was the subject of a book published in 1640, based on a discovery made
+by a shoemaker, Vicenzo Casciarolo, on a mountain-side near Bologna in
+1630.[2] Was the substance new which Brand showed to his friends? Johann
+Gottfried Leonhardi quotes a book of 1689 in which the author, Kletwich,
+claims that this phosphorus had already been known to Fernelius, the
+court physician of King Henri II of France (1154-1189).[3] To the same
+period belongs the "Ordinatio Alchid Bechil Saraceni philosophi," in
+which Ferdinand Hoefer found a distillation of urine with clay and
+carbonaceous material described, and the resulting product named
+escarbuncle.[4] It would be worth looking for this source; although
+Bechil would still remain an entirely unsuccessful predecessor, it does
+seem strange that in all the distillations of arbitrary mixtures, the
+conditions should never before 1669 have been right for the formation
+and the observation of phosphorus.
+
+[Illustration: Figure 1.--THE ALCHEMIST DISCOVERS PHOSPHORUS. A painting
+by Joseph Wright (1734-1779) of Derby, England.]
+
+For Brand's contemporaries at least, the discovery was new and exciting.
+The philosopher Gottfried Wilhelm von Leibniz (1646-1716) considered it
+important enough to devote some of his time (between his work as
+librarian in Hanover and Wolfenbuettel, his efforts to reunite the
+Protestant and the Catholic churches, and his duties as Privy Councellor
+in what we would call a Department of Justice) to a history of
+phosphorus. This friend of Huygens and Boyle tried to prove that Kunckel
+was not justified in claiming the discovery for himself.[5] Since then,
+it has been shown that Johann Kunckel (1630-1703) actually worked out
+the method which neither Brand nor his friend Kraft wanted to disclose.
+Boyle also developed a method independently, published it, and
+instructed Gottfried Hankwitz in the technique. Later on, Jean Hellot
+(1685-1765) gave a meticulous description of the details and a long
+survey of the literature.[6]
+
+[Illustration: Figure 2.--GALLEY-OVEN, 1869. The picture is a cross
+section through the front of the oven showing one of the 36 retorts, the
+receivers for the distillate, and the space in the upper story used for
+evaporating the mixture of acid solution of calcium phosphate and coal.
+(According to ANSELME PAYEN, _Precis de Chimie industrielle_, Paris,
+1849; reproduced from HUGO FLECK, _Die Fabrikation chemischer Produkte
+aus thierischen Abfaellen_, Vieweg, Braunschweig, 1862, page 80 of volume
+2, 2nd group, of P. BOLLEY'S _Handbuch der chemischen Technologie_.)]
+
+To obtain phosphorus, a good proportion of coal (regarded as a type of
+phlogiston) was added to urine, previously thickened by evaporation and
+preferably after putrefaction, and the mixture was heated to the highest
+attainable temperature. It was obvious that phlogiston entered into the
+composition of the distillation product. The question remained whether
+this product was generated _de novo_. In his research of 1743 to 1746,
+Andreas Sigismund Marggraf (1709-1782) provided the answer. He found the
+new substance in edible plant seeds, and he concluded that it enters the
+human system through the plant food, to be excreted later in the urine.
+He did not convince all the chemists with his reasoning. In 1789,
+Macquer wrote: "There are some who, even at this time, hold that the
+phosphorical ('phosphorische') acid generates itself in the animals and
+who consider this to be the 'animalistic acid.'"[7]
+
+Although Marggraf was more advanced in his arguments than these
+chemists, yet he was a child of his time. The luminescent and
+combustible, almost wax-like substance impressed him greatly. "My
+thoughts about the unexpected generation of light and fire out of water,
+fine earth, and phlogiston I reserve to describe at a later time." These
+thoughts went so far as to connect the new marvel with alchemical wonder
+tales. When Marggraf used the "essential salt of urine," also called
+_sal microcosmicum_, and admixed silver chloride ("horny silver") to it
+for the distillation of phosphorus, he expected "a partial conversion of
+silver by phlogiston and the added fine vitrifiable earth, but no trace
+of a more noble metal appeared."[8]
+
+Robert Boyle had already found that the burning of phosphorus produced
+an acid. He identified it by taste and by its influence on colored plant
+extracts serving as "indicators." Hankwitz[9] described methods for
+obtaining this acid, and Marggraf showed its chemical peculiarities.
+They did not necessarily establish phosphorus as a new element. To do
+that was not as important, at that time, as to conjecture on analogies
+with known substances. Underlying all its unique characteristics was the
+analogy of phosphorus with sulfur. Like sulfur, phosphorus can burn in
+two different ways, either slowly or more violently, and form two
+different acids. The analogy can, therefore, be extended to explain the
+results in both groups in the same way. In the process of burning, the
+combustible component is removed, and the acid originally combined with
+the combustible is set free. Whether the analogy should be pursued even
+further remained doubtful, although some suspicion lingered on for a
+while that phosphoric acid might actually be a modified sulfuric acid.
+Analogies and suspicions like these were needed to formulate new
+questions and stimulate new experiments. They are cited here for their
+important positive value in the historical development, and not for the
+purpose of showing how wrong these chemists were from our point of
+view, a point of view which they helped to create.
+
+The widespread interest in the burning of sulfur and of phosphorus,
+naturally, caught Lavoisier's attention. In his first volume of
+_Opuscules Physiques et Chimiques_ (1774), he devoted 20 pages to his
+experiments on phosphorus. He amplified them a few years later[10] when
+he attributed the combustion to a combination of phosphorus with the
+"eminently respirable" part of air. In the _Methode de Nomenclature
+Chimique_ of 1787, the column of "undecomposed substances" lists sulfur
+as the "radical sulfurique," and phosphorus, correspondingly, as the
+"radical phosphorique." The acids are now shown to be compounds of the
+"undecomposed" radicals, the complete reversion of the previous concept
+of this relationship. A part of the old analogy remained as far as the
+acids are concerned: sulfuric acid corresponds to phosphoric; sulfurous
+acid to phosphorous acid with less oxygen than in the former.[11]
+
+
+
+
+Early Uses
+
+
+In the 18th century, phosphorus was a costly material. It was produced
+mostly for display and to satisfy curiosity. Guillaume Francois Rouelle
+(1703-1770) demonstrated the process in his lectures, and, as Macquer
+reports, he "very often" succeeded in making it.[12] Robert Boyle had
+the idea of using phosphorus as a light for underwater divers.[13] A
+century later, "instant lights" were sold, with molten phosphorus as the
+"igniter," but they proved cumbersome and unreliable.[14] Because white
+phosphorus is highly poisonous, an active development of the use in
+matches occurred only after the conversion of the white modification
+into the red had been studied by Emile Kopp (1844), by Wilhelm Hittorf
+(1824-1914) and, in its practical application, by Anton Schroetter
+(1802-1875).[15]
+
+[Illustration: Figure 3.--DISTILLATION APPARATUS (1849) for refining
+crude phosphorus. The crude phosphorus is mixed with sand under hot
+water, cooled, drained, and filled into the retort. The outlet of the
+retort, at least 6 cm. in diameter, is partially immersed in the water
+contained in the bucket. A small dish, made from lead, with an iron
+handle, receives the distilled phosphorus. (From HUGO FLECK, _Die
+Fabrikation chemischer Produkte ..._ page 90.)]
+
+The most exciting early use, however, was in medicine. It is not
+surprising that such a use was sought at that time. Any new material
+immediately became the hope of ailing mankind--and of striving
+inventors.[16] Phosphorus was prescribed, in liniments with fatty oils
+or as solution in alcohol and ether, for external and internal
+application. A certain Dr. Kramer found it efficient against epilepsy
+and melancholia (1730). A Professor Hartmann recommended it against
+cramps.[17] However, in the growing production of phosphorus for
+matches, the workers experienced the poisonous effects. In the plant of
+Black and Bell at Stratford, this was prevented by inhaling turpentine.
+Experiments on dogs were carried out to show that poisoning by
+phosphorus could be remedied through oil of turpentine.[18]
+
+[Illustration: Figure 4.--APPARATUS FOR CONVERTING WHITE PHOSPHORUS into
+the red allotropic form, 1851. Redistilled phosphorus is heated in the
+glass or porcelain vessel (g) which is surrounded by a sandbath (e) and
+a metal bath (b). Vessel (j) is filled with mercury and water; together
+with valve (k), it serves as a safety device. The alcohol lamp (l) keeps
+the tube warm against clogging by solidified vapors. Because of hydrogen
+phosphides, the operation, carried out at 260 deg. C., had to be watched
+very carefully. (According to Arthur Albright, 1851; reproduced from
+HUGO FLECK, _Die Fabrikation chemischer Produkte ..._, page 112.)]
+
+
+
+
+Chemical Constitution of Phosphoric Acids
+
+
+In a long article on phosphorus, Edmond Willm wrote in 1876: "For a
+century, urine was the only source from which phosphorus was obtained.
+After Gahn, in 1769, recognized the presence of phosphoric acid in
+bones, Scheele indicated the procedure for making phosphorus from
+them."[19] Actually, Gahn used at first hartshorn (_Cornu cervi
+ustum_), and Scheele doubted, until he checked it himself, that his
+esteemed friend was right. A few years later, Scheele corrected Gahn's
+assumption that the _sal microcosmicum_ was an ammonia salt; instead, it
+is "a tertiary neutral salt, consisting of _alkali minerali fixo_ (i.e.,
+sodium), _alkali volatili_, and _acido phosphori_."[20]
+
+In the years after 1770, phosphorus was discovered in bones and many
+other parts of various animals. Treatment with sulfuric acid decomposed
+these materials into a solid residue and dissolved phosphoric acid. Many
+salts of this acid were produced in crystalline form. Heat resistance
+had been considered one of the outstanding characteristics of phosphoric
+acid. Now, however, in the processes of drying and heating certain
+phosphates, it became clear that three kinds of phosphoric acids could
+be produced: _ortho_, _pyro_, and _meta_.
+
+Berzelius cited these acids as examples of compounds which are ISOMERIC.
+This word was intended to designate compounds which contain the same
+number of atoms of the same elements but combined in different manners,
+thereby explaining their different chemical properties and crystal
+forms. It was in 1830 that Berzelius propounded this companion of the
+concept, ISOMORPHISM, which was to collect all cases of equal crystal
+form in compounds in which equal numbers of atoms of different elements
+are put together in the same manner. Together, the two concepts of
+isomerism and isomorphism seemed to cover all the known exceptions from
+the simplest assumption as to specificity and chemical composition.
+
+However, only a few years later Thomas Graham (1805-1869) proved that
+the three phosphoric acids are not isomeric. He used the proportion of 2
+P to 5 O in the oxide which Berzelius had thought justified at least
+until "an example of the contrary could be sufficiently
+established."[21] Refining the techniques of Gay-Lussac (1816) and
+several other investigators, Graham characterized the three phosphoric
+acids as "a terphosphate, a biphosphate, and phosphate of water."
+Actually, this was the wrong terminology for what he meant and
+formulated as trihydrate, bihydrate, and monohydrate of phosphorus
+oxide. In his manner of writing the formulas, each dot over the symbol
+for the element was to indicate an atom of oxygen; thus, he wrote:
+
+    ...   :: ..   ...    . .
+    H^{3} P  H^{2} P and H P.[22]
+
+[Illustration: Figure 5.--OVEN FOR THE CALCINATION OF BONES, about 1870.
+"The operation is carried out in a rather high oven, such as shown....
+The fresh bones are thrown in at the top of the oven, B. First, fuel in
+chamber F is lighted, and a certain quantity of bones is burnt on the
+grid D. When these bones are burning well, the oven is gradually filled
+with bones, and the combustion maintains itself without addition of
+other fuel. A circular gallery, C, surrounds the bottom of the oven and
+carries the products of combustion into the chimney, H. The calcined
+bones are taken out at the lower opening, G, by removing the bars of
+grid B." (Translation of the description from FIGUIER, _Merveilles de
+l'industrie_, volume 3, 1874, page 537.)]
+
+[Illustration: Figure 6.--AN ADVERTISEMENT with view of plant for
+manufacturing superphosphate about 1867. (From E. T. FREEDLEY,
+_Philadelphia and its Manufacturers in 1867_, page 288.)]
+
+Graham had come to this understanding of the phosphoric acids through
+his previous studies of "Alcoates, definite compounds of Salts and
+Alcohol analogous to the Hydrates" (1831). Liebig started from analogies
+he saw with certain organic acids when he formulated the phosphoric
+acids with a constant proportion of water (aq.) and varying proportions
+of "phosphoric acid" (P) as follows:
+
+    2 P 3 aq.  phosphoric acid
+    3 P 3 aq.  pyrophosphoric acid
+    6 P 3 aq.  metaphosphoric acid.
+
+[Illustration: Figure 7.--FLORIDA HARD-ROCK PHOSPHATE MINING. (From
+Carroll D. Wright, _The Phosphate Industry of the United States_, sixth
+special report of the Commissioner of Labor, Government Printing Office,
+Washington, 1893, plate facing page 43.)]
+
+Salts are formed when a "basis," i.e., a metal oxide, replaces water.
+When potassium-acid sulfate is neutralized by sodium base, the acid-salt
+divides into Glauber's salt and potassium sulfate, which proves the
+acid-salt to be a mixture of the neutral salt with its acid. Sodium-acid
+phosphate behaves quite differently. After neutralization by a potassium
+"base" (hydroxide), the salt does not split up; a uniform
+sodium-potassium phosphate is obtained. Therefore, phosphoric acid is
+truly three-basic![23]
+
+This result has later been confirmed, but the analogy by means of which
+it had been obtained was very weak, in certain parts quite wrong.
+
+The acids from the two lower oxides of phosphorus were also considered
+as three-basic. Adolphe Wurtz (1817-1884) formulated them in 1846,
+according to the theory of chemical types:
+
+    (PO)...
+            O^{3}  phosphoric acid
+      H^{3}
+
+    (PHO)..
+            O^{2}  phosphorus acid
+       H^{2}
+
+    (PH^{2}O).
+               O   hypophosphorous acid.[24]
+           H
+
+Further proof for these constitutions was sought in the study of the
+esters formed when the acids react with alcohols.
+
+Among the analogies and generalizations by which the research on
+phosphoric acid was supported, and to the results of which it
+contributed a full share, was the new theory of acids. Not oxygen,
+Lavoisier's general acidifier, but reactive hydrogen determines the
+character of acids. In this brief survey, it seems sufficient just to
+mention this connection without describing it in detail.
+
+The study of phosphoric acids led to important new concepts in
+theoretical chemistry. The finding of polybasicity was extended to other
+acids and formed the model that helped to recognize the
+polyfunctionality in other compounds, like alcohols and amines. The
+hydrogen theory of acids was fundamental for further advance. In another
+dimension, it is particularly interesting to see that large-scale
+applications followed almost immediately and directly from the new
+theoretical insight. The first and foremost of these applications was in
+agriculture.
+
+
+
+
+Phosphates as Plant Nutrients
+
+
+One hundred years after the discovery of "cold light," the presence of
+phosphorus in plants and animals was ascertained, and its form was
+established as a compound of phosphoric acid. This knowledge had little
+practical effect until the "nature" of the acid, in its various forms,
+was explained through the work of Thomas Graham. From it, there started
+a considerable technical development.
+
+At about that time (1833), the Duke of Richmond proved that the
+fertilizing value of bones resided not in the gelatin, nor in the
+calcium, but in the phosphoric acid. Thus, he confirmed what Theodore de
+Saussure had said in 1804, that "we have no reason to believe" that
+plants can exist without phosphorus. Unknowingly at first, the farmer
+had supplied this element by means of the organic fertilizers he used:
+manure, excrements, bones, and horns. Now, with the value of phosphorus
+known, a search began for mineral phosphates to be applied as
+fertilizers. Jean Baptiste Boussingault (1802-1887), an agricultural
+chemist in Lyons, traveled to Peru to see the guano deposits. Garcilaso
+de la Vega (ca. 1540 to ca. 1616) noted in his history of Peru (1604)
+that guano was used by the Incas as a fertilizer. Two hundred years
+later, Alexander von Humboldt revived this knowledge, and Humphry Davy
+wrote about the benefits of guano to the soil. Yet, the application of
+this fertilizer developed only slowly, until Justus Liebig sang its
+praise. Imports into England rose and far exceeded those into France
+where, between 1857 and 1867, about 50,000 tons were annually received.
+
+The other great advance in the use of phosphatic plant nutrients started
+with Liebig's recommendation (1840) to treat bones with sulfuric acid
+for solubilization. This idea was not entirely new; since 1832, a
+production of a "superphosphate" from bones and sulfuric acid had been
+in progress at Prague. At Rothamsted in 1842, John Bennet Lawes
+obtained a patent on the manufacture of superphosphate. Other
+manufactures in England followed and were successful, although James
+Muspratt (1793-1886) at Newton lost much time and "some thousands of
+pounds" on Liebig's idea of a "mineral manure."
+
+[Illustration: Figure 8.--FLORIDA LAND-PEBBLE PHOSPHATE MINING. (From
+Carroll D. Wright, _The Phosphate Industry of the United States ..._,
+plate facing page 58.)]
+
+It was difficult enough to establish the efficacy of bones and
+artificially produced phosphates in promoting the growth of plants under
+special conditions of soils and climate; therefore, the question as to
+the action of phosphates in the growing plant was not even seriously
+formulated at that time. The beneficial effects were obvious enough to
+increase the use of phosphates as plant nutrients and to call for new
+sources of supply. Active developments of phosphate mining and treating
+started in South Carolina in 1867, and in Florida in 1888.[25]
+
+In a reciprocal action, more phosphate application to soils stimulated
+increasing research on the conditions and reactions obtaining in the
+complex and varying compositions called soil. The findings of
+bacteriologists made it clear that physics and chemistry had to be
+amplified by biology for a real understanding of fertilizer effects.
+After 1900, for example, Julius Stoklasa (1857-1936) pointed out that
+bacterial action in soil solubilizes water-insoluble phosphates and
+makes them available to the plants.[26]
+
+[Illustration: Figure 9.--FLORIDA RIVER-PEBBLE PHOSPHATE MINING. (From
+Carroll D. Wright, _The Phosphate Industry of the United States ..._,
+plate facing page 64.)]
+
+The insight into the importance of phosphorus in organisms, especially
+since Liebig's time, is reflected in the work of Friedrich Nietzsche
+(1844-1900). This "re-valuator of all values" who modestly said of
+himself: "I am dynamite!" once explained the human temperaments as
+caused by the inorganic salts they contain: "The differences in
+temperament are perhaps caused more by the different distribution and
+quantities of the inorganic salts than by everything else. Bilious
+people have too little sodium sulfate, the melancholics are lacking in
+potassium sulfate and phosphate; too little calcium phosphate in the
+phlegmatics. Courageous natures have an excess of iron phosphate." (See
+volume 12 of _Nietzsche's Works_, edit. Naumann-Kroener, Leipzig, 1886.)
+In this strange association of inorganic salts with human temperaments,
+the role of iron phosphate as a producer of courage is particularly
+interesting. What would a modern philosopher conclude if he followed the
+development of insight into the composition and function of complex
+phosphate compounds in organisms?
+
+
+
+
+From Inorganic to Organic Phosphates
+
+
+By the middle of the 19th century, the source of phosphorus in natural
+phosphates and the chemistry of its oxidation products had been
+established. The main difficulty that had to be overcome was that these
+oxidation products existed in so many forms, not only several stages of
+oxidation, but, in addition, aggregations and condensations of the
+phosphoric acids. Once the fundamental chemistry of these acids was
+elucidated, the attention of chemists and physiologists turned to the
+task of finding the actual state in which phosphorus compounds were
+present in the organisms. It had been a great advance when it had been
+shown that plants need phosphates in their soil. This led to the next
+question concerning the materials in the body of the plant for which
+phosphates were being used and into which they were incorporated.
+Similarly, the knowledge that animals attain their phosphates from the
+digested plant food called, in the next step of scientific inquiry, for
+information on the nature of phosphates produced from this source.
+
+The method used in this inquiry was to subject anatomically separated
+parts of the organisms to chemical separations. The means for such
+separations had to be more gentle than the strong heat and destructive
+chemicals that had been considered adequate up to then. The
+interpretation of the new results naturally relied on the general
+advance of chemistry, the development of new methods for isolating
+substances of little stability, of new concepts concerning the
+arrangements of atoms in the molecules, and of new apparatus to measure
+their rates of change.
+
+In the system of chemistry, as it developed in the first half of the
+19th century, the new development can be characterized as the turn from
+inorganic to organic phosphates, from the substance of minerals and
+strong chemical interactions to the components in which phosphate groups
+remained combined with carbon-containing substances.
+
+[Illustration: Figure 10.--ELECTRIC FURNACE FOR PRODUCING ELEMENTAL
+PHOSPHORUS, invented by Thomas Parker of Newbridge, England, and
+assigned to The Electric Construction Corporation of the same place. The
+drawing is part of United States patent 482,586 (September 13, 1892).
+The furnace was patented in England on October 29, 1889 (no. 17,060); in
+France on June 23, 1890 (no. 206,566); in Germany on June 17, 1890 (no.
+55,700); and in Italy on October 23, 1890 (no. 431). The following
+explanation is cited from the U.S. patent:
+
+Figure 1 [shown here] is a vertical section of the furnace, and Fig. 2
+is a diagram to illustrate the means for regulating the electro-motive
+force or quantity of current across the furnace.
+
+F is the furnace containing the charge to be treated. It has an
+inlet-hopper at _a_, with slides AA, by which the charge can be admitted
+without opening communication between the interior of the furnace and
+the outer air.
+
+B is a screw conveyer by which the charge is pushed forward into the
+furnace.
+
+_c'c'_ are the electrodes, consisting of blocks or cylinders or the like
+of carbon fixed in metal socket-pieces _c c_, to which the
+electric-circuit wires _d_ from the dynamo D are affixed. The current,
+as aforesaid, may be either continuous or alternating. _c^{2}c^{2}_ are
+rods of metal or carbon, which are used to establish the electric
+circuit through the furnace, the said rods being inserted into holes in
+conductors _c^{3}_ (in contact with the socket-pieces _c_) and in the
+furnace, as shown.
+
+_g_ is the outlet for the gas or vapor, _h_ the slag-tap hole, and _x_
+the opening for manipulating the charge, the said openings being closed
+by clay or otherwise when the furnace is at work.
+
+I use coke or other form of carbon in the charge between the electrodes
+_c'_, the said coke being in contact with the said electrodes, so that
+complete incandescence is insured.
+
+A means for varying the electro-motive force or quantity of current
+across the furnace with the varying resistance of the charge is
+illustrated by the diagram, Fig. 2. _c' c^{2}_ indicate the electrodes
+in the furnace, as in Fig. 1, and D is the dynamo and T its terminals. E
+represents the exciting-circuit. R R are resistances, and R S is the
+resistance-switch, which is operated to put in more or less resistance
+at R as the resistance of the charge in the furnace lessens or
+increases. This switch may be automatically operated, and a suitable
+arrangement for the purpose is a current-regulator such as is described
+in the specification of English Letters Patent No. 14,504, of September
+14, 1889, granted to William Henry Douglas and Thomas Hugh Parker.]
+
+[Illustration:
+
+  T. PARKER.
+  ELECTRICAL FURNACE.
+
+  Patented Sept. 13, 1892.
+
+  FIG. 1.]
+
+[Illustration: FIG. 2.
+
+  _Inventor
+  Thomas Parker_
+
+  _By his attorneys
+  Howson and Howson_
+
+  _Witnesses:
+  George Baumann
+  John Revell_]
+
+[Illustration: Figure 11.--DIPPING OF MATCHSTICKS in France, about 1870.
+The frame which holds the matches so that one end protrudes at the
+bottom, is lowered over a pan containing molten sulfur. The
+sulfur-covered matches are then dropped into a phosphorous paste. See
+figure 12. (From FIGUIER, _Merveilles de l'industrie_, volume 3, 1874,
+page 575.)]
+
+
+
+
+Phosphatides and Phosphagens
+
+
+The important phosphorus compounds in organisms are much more complex
+than the simple salts, to which Nietzsche attributed such influence on
+man's character. Long before he wrote, it was known that phosphoric acid
+combines not only with inorganic bases to form salts, but with alcohols
+to form esters. In the middle of the 19th century, Theophile Juste
+Pelouze (1807-1867) extended this knowledge to an ester of glycerol.
+This proved to be significant in several respects. Glycerol had been
+shown by Michel Chevreul (1786-1889) as the substance in fats that is
+released in the process of soap boiling, when the fatty acids are
+converted into their salts. That it has the nature of an alcohol had
+been demonstrated by Marcellin Berthelot. Instead of one "alcoholic"
+hydroxyl group, OH, like ethanol (the alcohol of fermentation), or two
+hydroxyl groups (like ethylene glycol), glycerol contains three such
+groups. It was the only "natural" alcohol known at that time. That this
+alcohol would combine with phosphoric acid could be predicted, but that
+the ester, as obtained by Pelouze, still contained free acidic functions
+and formed a water-soluble barium salt was a new experience.
+
+[Illustration: Figure 12.--PAN FOR DIPPING MATCHSTICKS into phosphorus
+paste, about 1870. The letters on the picture are: A, matches; B, water
+bath; C, frame; D, plate; E, phosphorus paste; F, oven. The phosphorus
+paste of Boettger, 1842, contained 10 phosphorus, 25 antimony sulfide,
+12.5 manganese dioxide, 15 gelatin. According to Figuier (page 579), R.
+Wagner substituted lead dioxide for the manganese dioxide. (From
+FIGUIER, volume 3, 1874, page 576.)]
+
+
+ALCOHOLIC FERMENTATION
+
+  (C_{6}H_{10}O_{5})_{_n_}   C_{6}H_{12}O_{6}      C_{6}H_{12}O_{6}
+      glycogen                  glucose                 fructose
+         ^|                        ^|                      ^|
+         || H_{3}PO_{4}            || <-- ATP              || <--ATP
+         |v                        |v                      |v
+      ---------------+          ------+
+   H--C--OPO_{3}H_{2}|       H--C--OH |              H _{2}C--OH
+      |              |          |     |                    |
+   H--C--OH          |       H--C--OH |                    C--(OH)--+
+      |              |          |     |                    |        |
+  HO--C--H           O <==> HO--C--H  O   <=======>    HO--C--H     |
+      |              |          |     |                    |        O
+   H--C--OH          |       H--C--OH |                 H--C--OH    |
+      |              |          |     |                    |        |
+   H--C--------------+       H--C-----+                 H--C--------+
+      |                         |                          |
+      CH_{2}OH             H_{2}C--OPO_{3}H_{2}+ADP   H_{2}C--OPO_{3}H_{2}+ADP
+
+  glucose-1-phosphate        glucose-6-phosphate        fructose-6-phosphate
+  (Cori-ester)               (Robison-ester)            (Neuberg-ester)
+                                                          ^   |
+                                                          |   | <-- ATP
+                                                     +----|   |
+                                                     | +------|
+                                                     | |
+                                                     | v
+                                             H_{2}C--OPO_{3}H_{2}
+                                                  |
+                                                  C(OH)--+
+                                                  |      |
+                                              HO--C--H   |
+                 fructose-1,6-diphosphate         |      O
+                  (Harden-Young-ester)         H--C--OH  |
+                                                  |      |
+                                               H--C------+
+                                                  |
+                                             H_{2}C--OPO_{3}H_{2} + ADP
+                                                  ^|
+                                                  ||  O
+                                                  || //
+                             CH_{2}OPO_{3}H_{2}   || CH
+                             |                    |v |  3-phosphoglycer-aldehyde
+  dihydroxyacetone-phosphate C=O   <=============>   CHOH  (Fischer-ester)
+                             |                       |
+                             CH_{2}OH                CH_{2}OPO_{3}H_{2}
+                                                    ||  + coenzyme + H_{3}PO_{4}
+                                                  O=C--OPO_{3}H_{2}
+                                                    |
+          1,3-diphosphoglyceric acid                CHOH + dihydro-coenzyme
+           (Negelein-ester)                         |
+                                                    CH_{2}OPO_{3}H
+                                                   ^|
+                                           ADP --> ||
+                                                   || O
+                                                   |v//
+                                                    C--OH
+                                                    |      +---+
+             3-phosphoglyceric acid                 CHOH + |ATP|
+               (Nilsson-ester)                      |      +---+
+                                                    CH_{2}OPO_{3}H_{2}
+                                                   ^|
+                                                   |v
+                                                    COOH
+             2-phosphoglyceric acid                 |
+                                                    CHOPO_{3}H_{2}
+                                                    |
+                                                    CH_{2}OH
+                                                   ^|
+                                                   |v
+                                                    COOH
+                                                    |
+                 phosphopyruvic acid                COPO_{3}H_{2}
+                  (enol-)                          ||
+                                                    CH_2
+                                           ADP --> ||
+                                                    COOH
+                  +------+                          |     +---+
+                  |CO_{2}| + CH_3CHO    <--------   C=O + |ATP|
+                  +------+   acetaldehyde           |     +---+
+                  carbon    |                       CH_{3}
+                  dioxide   | + dihydro-coenzyme  pyruvic acid
+                            |
+                            v
+                     +----------------+
+                     | CH_{3}CH_{2}OH | + coenzyme
+                     +----------------+
+                      ethyl alcohol
+
+[Illustration: Figure 13.--SURVEY OF ALCOHOLIC FERMENTATION, 1951. The
+"well-known scheme of alcoholic fermentation" according to Albert Jan
+Kluyver (1888-1956), presented before the Society of Chemical Industry
+in the Royal Institution, March 7, 1951. In _Chemistry & Industry_,
+1952, page 136 ff., Kluyver restates that "... the fermentation of one
+molecule of glucose is indissolubly connected with the formation of two
+molecules of adenosine triphosphate (ATP) out of two molecules of
+adenosine diphosphate (ADP)."]
+
+Shortly after this experience had been gained, it became valuable for
+understanding the chemical nature of a new substance extracted from a
+natural organ. This substance was named lecithin by its discoverer,
+Nicolas Theodore Gobley[27] (1811-1876), because he obtained it from egg
+yolk (in Greek, _lekidos_). He used ether and alcohol for this
+extraction. Had he used water and mineral acid instead, he would not
+have found lecithin, but only its components. As Gobley and, slightly
+later, Oscar Liebreich (1839-1908), subjected lecithin to treatment with
+boiling water and acid, they separated it into three parts. One of them
+was the glycerophosphoric acid of Pelouze, the second was the well-known
+stearic acid of Chevreul, but the third was somewhat mysterious. This
+third substance was the same as one previously noticed when nerves had
+been subjected to an extraction by boiling water and acid and,
+therefore, called nerve-substance or neurine. Adolf Friedrich Strecker
+(1822-1871) established the identity of this neurine with a product he
+had extracted from bile and which went under the name of choline.
+Adolphe Wurtz (1817-1884) succeeded in synthesizing this substance from
+ethylene oxide, CH_2.O.CH_2 and trimethylamine N(CH_3)_3.[28] Thus, all
+three parts were identified, and Strecker put them together to construct
+a chemical formula for lecithin, glycerophosphoric acid combined with a
+fatty acid and with choline (a hydrate of neurine).
+
+                        { OH       }
+                      N { (CH_3)_3 } Choline
+                        { C_2H_4O  }
+
+
+    C_18H_33O_2 }               HO }
+                }                  } PO
+    C_16H_31O_2 }          C_3H_5O }
+
+    Fatty Acids        Glycerophosphate
+          \--------v-------/
+               Lecithin
+          according to Strecker
+
+This formula was not quite correct. Richard Willstaetter showed that an
+internal neutralization takes place between the amino group and the free
+acidic residue. This is expressed in his lecithin formula of 1918.
+
+    CH_{2}.O.R
+    |
+    CH_{2}.O.R_2
+    |
+    |           O.CH_{2}.CH_{2}
+    |          /          \
+    CH_{2}.O--P=O         N(CH_{3})_{3}
+               \          /
+                \---O----/
+
+[Illustration: Lecithin (1918)]
+
+When the aim was to distill elementary phosphorus out of an organic
+material, it did not matter whether this was fresh or putrified. For
+obtaining lecithin out of egg yolk and similar materials, it was
+essential to use it in fresh condition. Otherwise, enzymes would have
+decomposed it. Through more recent work, four enzymes have been
+separated, which act specifically in decomposing lecithin. Enzyme A
+removes one fatty acid and leaves a complex residue, called
+lysolecithin, intact. Enzyme B attacks this residue and splits off the
+remaining fatty acid group from it, enzyme C liberates only the choline
+from lecithin, and enzyme D opens lecithin at the ester bond between
+glycerol and phosphoric acid. This is shown in the following diagram.
+
+    ENZYMATIC SPLITTING OF LECITHINS
+
+    ENZYME SUBSTRATE     PRODUCTS
+
+    A      Lecithin      Lysolecithin and fatty
+                           acids.
+
+    B      Lysolecithin  Glycero-phospho-choline
+                           and fatty acids.
+
+    C      Lecithin      Phosphatidic acid and
+                           choline.
+
+    D      Lecithin      Phosphoryl choline and
+                           diglyceride.
+
+Several fatty acids can be present in lecithin from various sources:
+palmitic and oleic acid, besides the stearic acid which at first had
+been thought the only one involved. In another group of extracts from
+brain or nerve tissue, amino-ethanol H_{2}NCH_{2}CH_{2}OH is found
+instead of the choline of lecithin. The variations include the alcohol,
+to which the fatty acids and choline phosphate are attached, for
+example, glycerol can be replaced by the so-called meat-sugar, inositol,
+which has six hydroxyl groups in its hexagon-shaped molecule
+C_{6}H_{6}(OH)_{6}.
+
+[Illustration: Figure 14.--EDUARD BUCHNER (1860-1917) received the Nobel
+Prize in Chemistry for his discovery of cell-free fermentation, the
+first step in finding the role of phosphate in fermentations (1907).]
+
+The generally similar behavior of these phosphate-and fat-containing
+substances was emphasized by Ludwig Thudichum (1829-1901). He coined the
+name phosphatides for this group of substances from seeds and
+nerves.[29] His work on the phosphates in brain substance aroused
+particular interest. When William Crookes drew his highly imaginative
+picture of an "evolution" of the chemical elements, he put into it
+"phosphorus for the brain, salt for the sea, clay for the solid
+earth...."[30] But phosphatides occur in many places of organisms, in
+bacteria, in leaves and roots of plants, in fat and tissues of animals.
+And where phosphatides are found, there are also enzymes that
+specifically act on them. They are called phosphatases to imply that
+they split the phosphatides. In addition, enzymes are present, which
+transfer phosphate groups from one compound to another. They are more
+abundant in seeds of high fat content than in the more starch-containing
+seeds, but even potatoes and orange juice have phosphatases.[31]
+
+Thus, from phosphatides, phosphoric acid is generated, and they could
+also be called phosphagens. Since 1926, however, the name phosphagens
+has been reserved for a group of organic substances that release their
+phosphoric acid very readily. The link between phosphorus and carbon is
+provided by oxygen in the phosphatides, by nitrogen in the phosphagens.
+In vertebrates, the basis for the phosphoric acid is creatine, whereas
+invertebrates have arginine instead.
+
+      H    OH                   OH
+      |   /                    /
+      N--P=O              NH--P=O
+     /    \              /     \
+    C=NH   OH           C=NH    OH
+     \                   \
+      N--CH_{2}COOH       NH
+      |                   |
+      CH_{3}              CH_{2}
+                          |
+    Creatine phosphate    CH_{2}
+                          |
+                          CH_{2}
+                          |
+                          CHNH_{2}
+                          |
+                          COOH
+
+                       Arginine phosphate
+
+
+
+
+Nuclein and Nucleic Acids
+
+
+All parts of an organism are essential for life. Only with this in mind
+does it make sense to say that the most important part of the cell is
+its nucleus. From the nuclei of cells in pus and in salmon sperm, Johann
+Friedrich Miescher (1811-1887) obtained a peculiar kind of substance,
+which he named nuclein (1868). Its phosphate content was easily
+discovered, but to find the exact proportions and the nature of the
+other components required special methods of separation from
+phosphatides and other proteins. It was difficult to develop such
+methods at a time when little was known about the properties, and
+particularly the stability, of a nuclein. For preparing nuclein from
+yeast cells, Felix Hoppe-Seyler (1825-1895) described the following
+details: Yeast is dispersed in water to extract soluble materials, like
+salts or sugars. After a few hours, the insoluble material is separated,
+washed once more with water, and then extracted with a very dilute
+solution of sodium hydroxide. The slightly alkaline solution, freed from
+insoluble residues, is slowly added to a weak hydrochloric acid. A
+precipitate forms which is separated by filtration, washed with dilute
+acid, then with cold alcohol, and finally extracted by boiling alcohol.
+The dried residue is the nuclein.[32] It contains six percent
+phosphorus. A little more washing with water, a slightly longer
+treatment with acid or alcohol gives products of lower phosphorus
+content. Many experimental variations were necessary to establish the
+procedure that leads to purification without alteration of the natural
+substance.
+
+This was also true for the methods of chemical degradation, carried out
+in order to find the components of nucleins in their highest state of
+natural complexity. It was learned for example, that the special kind of
+carbohydrate present in nucleins was very susceptible to change under
+the conditions of hydrolysis by acids. Phoebus Aaron Theodor Levine
+(1869-1940), therefore, used the digestion by a living organism. With E.
+S. London, he introduced a solution of nucleic acid into, e.g., the
+gastrointestinal segment of a dog through a gastric fistula and withdrew
+the product of digestion through an intestinal fistula. Fortunately, the
+products obtained in such degradations were not new in themselves. The
+carbohydrate in this nucleic acid proved to be identical with D-ribose,
+which Emil Fischer had artificially made from arabinose and named ribose
+to indicate this relationship (1891). The nitrogenous products of the
+degradation were identical with substances previously prepared in the
+long study of uric acid. In the course of this study, Emil Fischer
+established uric acid and a number of its derivatives as having the
+elementary skeleton of what he called "pure uric acid," abbreviated to
+purine. Out of Adolf Baeyer's work on barbituric acid came the knowledge
+of pyrimidine and its derivatives.
+
+[Illustration: Figure 15.--ALBRECHT KOSSEL (1853-1927) received the
+Nobel Prize in Medicine and Physiology in 1910 for his work on nucleic
+substances, which contain a high proportion of phosphorus. The chemical
+bonds of this phosphorus in the molecules of nucleic substances were
+determined in later work. (_Photo courtesy National Library of Medicine,
+Washington, D.C._)]
+
+From these findings, together with what Oswald Schmiedeberg (1838-1921)
+had established concerning the presence of four phosphate groups in the
+molecule (1899), Robert Feulgen (1884-1955) constructed the following
+scheme of a nucleic acid. Feulgen's formula of 1918 is:
+
+    Phosphoric acid--Carbohydrate--Guanine
+    Phosphoric acid--Carbohydrate--Cytosine
+    Phosphoric acid--Carbohydrate--Thymine
+    Phosphoric acid--Carbohydrate--Adenine
+
+Of the four basic components on the right, thymine occurs in the nucleic
+acid from the thymus gland. Yeast contains uracil instead. The
+difference between these two bases is one methyl group: thymine is a
+5-methyluracil. In all of these basic substances, the structure of urea
+
+      NH_{2}
+     /
+    C=O
+     \
+      NH_{2}
+
+is involved, and they form pairs of oxidized and reduced states:
+
+         PURINE              PYRIMIDINE
+
+     (reduced) Adenine + (oxidized) Thymine
+    (oxidized) Guanine + (reduced)  Cytosine
+
+       3N = CH4
+        |   |
+    2H--C   CH5
+        ||  ||
+        1N--CH6
+
+    Pyrimidine
+
+       1N==CH6
+        |  |    H
+        |  |  7/          N==C--NH_{2}
+    2H--C  C--N           |  |
+        || ||5 \       H--C  C--NH
+        || ||   \         || ||  \
+        || ||    CH8      || ||   CH
+        || ||   //        || ||  //
+        3N--C--N          N--C--N
+            4  9
+                         Adenine
+         Purine
+
+           HN--C=O
+            |  |
+    NH_{2}--C  C--NH       N==C--NH_{2}  H--N--C=O
+            || ||  \       |  |             |  |
+            || ||   CH   O=C  C--H        O=C  CH
+            || ||  //      |  ||            |  ||
+            N--C--N     H--N--CH           HN--CH
+
+         Guanine         Cytosine         Uracil
+
+  The carbohydrate is ribose or deoxyribose.
+
+        CHO            CHO
+        |              |
+     H--C--OH      HO--C--H
+        |              |
+    HO--C--H       HO--C--H
+        |              |
+    HO--C--H       HO--C--H
+        |              |
+        CH_{2}OH       CH_{2}OH
+
+    Arabinose      L-Ribose
+
+       Fischer and Piloty, 1891
+
+     H
+      \(1)/-----O-----\(4) (5)
+        C              CH--CH_{2}OH
+      /   \(2)     (3)/
+    HO     CH_{2}--HC(OH)
+
+            Deoxyribose
+
+The exact position of phosphoric acid was established after long work
+and verified by synthesis.[33]
+
+A compound of adenine, ribose, and phosphoric acid was found in yeast,
+blood, and in skeletal muscle of mammals. From 100 grams of such muscle,
+0.35-0.40 grams of this compound were isolated. If the muscle is at
+rest, the compound contains three molecules of phosphoric acid, linked
+through oxygen atoms. It was named adenosine triphosphate or
+adenyltriphosphoric acid,[34] usually abbreviated by the symbol ATP. It
+releases one phosphoric acid group very easily and goes over in the
+diphosphate, ADP, but it can also lose 2 P-groups as pyrophosphoric acid
+and leave the monophosphate, AMP.
+
+     N==C--NH_{2}
+     |  |
+    HC  C--N     +----O----+
+     || ||  \\   |         |
+     || ||   CH  |  OH  OH |  H       OH
+     || ||  /    |  |   |  |  |      /
+     N--C--N-----C--C---C--C--C--O--P=O
+                 |  |   |  |  |      \
+                 H  H   H  H  H       OH
+    \---------/\---------------/\--------/
+      Adenine      D-Ribose      Phosphoric
+                                   acid
+
+This change of ATP was considered to be the main source of energy in
+muscle contraction by Otto Meyerhof.[35] The corresponding derivatives
+of guanine, cytosine, and uracil were also found, and they are active in
+the temporary transfer of phosphoric acid groups in biological
+processes.
+
+Thus, the study of organic phosphates progressed from the comparatively
+simple esters connected with fatty substances of organisms to the
+proteins and the nuclear substances of the cell. The proportional amount
+of phosphorus in the former was larger than in the latter; the actual
+importance and function in the life of organisms, however, is not
+measured by the quantity but determined by the special nature of the
+compounds.
+
+[Illustration: Figure 16.--OTTO MEYERHOF (1884-1951) received one-half
+of the Nobel Prize in Medicine and Physiology in 1922 for his discovery
+of the metabolism of lactic acid in muscle, which involves the action of
+phosphates, especially adenosine duophosphates. (_Photo courtesy
+National Library of Medicine, Washington, D.C._)]
+
+[Illustration: Figure 17.--ARTHUR HARDEN (1865-1940), left, AND HANS A.
+S. VON EULER-CHELPIN (b. 1875), right, shared the Nobel Prize in
+Chemistry in 1929. Harden received it for his research in fermentation,
+which showed the influence of phosphate, particularly the formation of a
+hexose diphosphate. Euler-Chelpin received his award for his research in
+fermentation. He found coenzyme A which is a nucleotide containing
+phosphoric acid.]
+
+[Illustration: Figure 18.--GEORGE DE HEVESY (b. 1885) received the Nobel
+Prize in Chemistry in 1943 for his research with isotopic tracer
+elements, particularly radiophosphorus of weight 32 (ordinary phosphorus
+is 31).]
+
+[Illustration: Figure 19.--CARL F. CORI (b. 1896) AND HIS WIFE, GERTY T.
+CORI (1896-1957) received part of the Nobel Prize in Medicine and
+Physiology in 1947 for their study on glycogen conversion. In the course
+of this study, they identified glucose 1-phosphate, now usually referred
+to as "Cori ester," and its function in the glycogen cycle. (_Photo
+courtesy National Library of Medicine, Washington, D.C._)]
+
+The study of this function is the newest phase in the history of
+phosphorus and represents the culmination of the previous efforts. This
+newest phase developed out of an accidental discovery concerning one of
+the oldest organic-chemical industries, the production of alcohol by the
+fermentative action of yeast on sugar. A transition of carbohydrates
+through phosphate compounds to the end products of the fermentation
+process was found, and it gradually proved to be a kind of model for a
+host of biological processes.
+
+Specific phosphates were thus found to be indispensable for life. In
+reverse, the wrong kind of phosphates can destroy life. As a result, an
+important part of the new phase in phosphorus history consisted in the
+study--and use--of antibiotic phosphorus compounds.
+
+
+
+
+Phosphates in Biological Processes
+
+
+The first indication that phosphorus is important for life came from the
+experience that plants take it up from the substances in the soil. They
+incorporate it in their body substance. What makes phosphorus so
+important that they cannot grow without it? The next insight was that
+animals acquire it from their plant food. It is then found in bones, in
+fat and nerve tissue, in all cells and particularly in the cell nuclei.
+What are its functions there?
+
+The answers to such questions were developed from the study of a
+long-known process, the conversion of carbohydrates into carbon dioxide
+and alcohol by yeast. It started with Eduard Buchner's discovery of
+1890, that fermentation is produced by a preparation from yeast in which
+all living cells have been removed. When yeast is dead-ground and
+pressed out, the juice still has the ability to produce fermentation.
+
+It is strange, but in many ways characteristic for the process of
+science, that the "riddle" of phosphorus in life was solved by first
+eliminating life. In such "lifeless" fermentations, Arthur Harden found
+that the conversion of sugar begins with the formation of a hexose
+phosphate (1904). The "ferment" of yeast, called zymase, proved to be a
+composite of several enzymes. Hans von Euler-Chelpin isolated one part
+of zymase, which remains active even after heating its solution to the
+boiling point. From 1 kilogram of yeast, he obtained 20 milligrams of
+this heat-stable enzyme, which he called cozymase and identified as a
+nucleotide composed of a purine, a sugar, and phosphoric acid.[36] In
+the years between the two World Wars, zymase was further resolved into
+more enzymes, one of them the coenzyme I, which was shown to be ADP
+connected with another molecule of ribose attached to the amide of
+nicotinic acid, or diphosphopyridine nucleotide:
+
+       ^                           NH_{2}
+      / \\                         |
+     /   \\                    N   ^
+     ||   |-CONH_{2}          //\ / \\
+     ||   |                   |  ||  N
+     \   //                   |  ||  |
+       N_{+}                  N--+   |
+       |                      |   \//
+       |                      |    N
+    H--C------+            H--C------+
+       |      |               |      |
+    H--C--OH  |            H--C--OH  |
+       |      O               |      O
+    H--C--OH  |            H--C--OH  |
+       |      |               |      |
+    H--C------+   O     O  H--C------+
+       |          ||    ||    |
+       CH_{2}--O--P--O--P--O--CH_{2}
+                  |     |
+                  O-    OH
+
+                 Coenzyme I
+
+[Illustration: Figure 20.--FRITZ A. LIPMANN (b. 1899) shared with Hans
+Adolf Krebs the Nobel Prize in Medicine and Physiology in 1953 for his
+work on coenzyme A. He discovered acetyl phosphate as the substance in
+bacteria, which transfers phosphate to adenylic acid.]
+
+[Illustration: Figure 21.--ALEXANDER R. TODD (b. 1907) received the
+Nobel Prize in Chemistry in 1957 for his research on nucleotides. He
+determined the position of the phosphate groups in the molecule and
+confirmed it by synthesis of dinucleotide phosphates.]
+
+Its function is connected with the transfer of hydrogen between
+intermediates formed through phosphate-transferring enzymes.
+Fermentation proceeds by a cascade of processes, in which phosphate
+groups swing back and forth, and equilibria between ATP with ADP play a
+major role.
+
+Many of the enzymes are closely related to vitamins. Thus, cocarboxylase
+A, which takes part in the separation of carbon dioxide from an
+intermediate fermentation product, is the phosphate of vitamin B_{1}.
+Others of the B vitamins contain phosphate groups, for example those of
+the B_{2} and B_{6} group, and in B_{12}, one lonely phosphate forms a
+bridge in the large molecule that contains one atom of cobalt:
+C_{63}H_{90}N_{14}O_{14}PCo. The formation of vitamin A from carotine
+occurs under the influence of ATP.
+
+The first stages in fermentation are like those in respiration, which
+ends with carbon dioxide and water. These two are the materials for the
+reverse process in photosynthesis. When light is absorbed by the
+chlorophyll of green plants, one of the initial reactions is a transfer
+of hydrogen from water to a triphosphopyridine nucleotide, which later
+acts to reduce the carbon dioxide. Under the influence of ATP,
+phosphoglyceric acid is synthesized and further built up by way of
+carbohydrate phosphates to hexose sugars and finally to starch. In many
+starchy fruits, a small proportion of phosphate remains attached to the
+end product.
+
+The synthesis of proteins is under the control of deoxyribonucleic acid
+or ribonucleic acid, abbreviated by the symbols DNA and RNA. The genes
+in the nucleus are parts of a giant DNA molecule. RNA is a universal
+constituent of all living cells. Where protein synthesis is intense, the
+content in RNA is high. Thus, the spinning glands of silkworms are
+extraordinarily rich in RNA.[37]
+
+In his research on the radioactive isotope P^32, George de Hevesy gained
+some insight into the surprising mobility of phosphates in organisms: "A
+phosphate radical taken up with the food may first participate in the
+phosphorylation of glucose in the intestinal mucose, soon afterwards
+pass into the circulation as free phosphate, enter a red corpuscle,
+become incorporated with an adenosine triphosphoric-acid molecule,
+participate in a glycolytic process going on in the corpuscle, return to
+circulation, penetrate into the liver cells, participate in the
+formation of a phosphatide molecule, after a short interval enter the
+circulation in this form, penetrate into the spleen, and leave this
+organ after some time as a constituent of a lymphocyte. We may meet the
+phosphate radical again as a constituent of the plasma, from which it
+may find its way into the skeleton."[38] Much has been added in the last
+30 years to complete this picture in many details and to extend it to
+other biochemical processes, including even the changes of the pigments
+in the retina in the visual process, or in the conversion of chemical
+energy to light by bacteria and insects.
+
+
+
+
+Medicines and Poisons
+
+
+In the delicate balance of these processes, disturbances may occur which
+can be remedied by specific phosphate-containing medicines. Thus,
+adenosine phosphate has been recommended in cases of angina pectoris
+and marketed under trade names like sarkolyt, or in compounds named
+angiolysine. A considerable number of physiologically active organic
+phosphates can be found in the patent literature.[39] Yeast itself is
+considered to be a valuable food additive.
+
+On the other hand, there are phosphate compounds that act as poisons.
+One group of such compounds was discovered in 1929 by W. Lange, who
+wrote: "Of interest is the strong action of mono-fluorophosphate esters
+on the human body--the effect is produced by very small quantities."[40]
+Diisopropyl fluorophosphate has since become a potential agent for
+chemical warfare. It inactivates an enzyme which controls the
+transmission of nerve impulses to muscle, acetylcholine esterase.
+
+Organic esters of phosphoric acids are used as insecticides. The
+hexa-ethylester of tetraphosphoric acid, prepared by Gerhard Schrader by
+heating triethylphosphate with phosphorus oxychloride,[41] actually
+contains tetraethylpyrophosphate (TEPP) among others. Bayer's Dipterex,
+the dimethyl ester of 2,2,2-trichloro-1-hydroxyethyl-phosphonate, has
+been modified to dimethyl-2,2-dichlorovinyl-phosphate and is especially
+active against the oriental fruit fly.[42]
+
+[Illustration: Figure 22.--ARTHUR KORNBERG (b. 1918) AND SEVERO OCHOA
+(b. 1905) shared the Nobel Prize in Medicine and Physiology in 1959.
+Kornberg received it for research on the biological synthesis of
+deoxyribonucleic acid. In particular, he found that four triphosphate
+components and a small amount of the end product as a "template" had to
+be present for the enzymatic synthesis. Ochoa received his share of the
+prize for research in ribonucleic acid and deoxyribonucleic acid. In
+particular, Ochoa synthesized polyribonucleotides and used the
+radioactive isotope, P^{32}. The synthetic polyribonucleotides were
+found to resemble the natural substances in all essentials.]
+
+        Cl H  O
+        |  | || OCH_{3}
+        |  | ||/
+    Cl--C--C--P             Bayer's L 13/59
+        |  |   \              (Dipterex)
+        |  |    OCH_{3}
+        Cl OH
+
+    (CH_{3})_{2}N O     O  N(CH_{3})_{2}
+                 \||    ||/
+                  P--O--P                  Schradan
+                 /       \
+    (CH_{3})_{2}N         N(CH_{3})_{2}
+
+         Octamethylpyrophosphoramide
+
+[Illustration: Figure 23.--MELVIN CALVIN (b. 1911) received the Nobel
+Prize in Chemistry in 1961 for his research in photosynthesis, in which
+he specified the function of phosphoglyceric acid as an intermediate in
+the synthesis of carbohydrates from carbon dioxide and water by green
+plants.]
+
+The story of phosphorus, which began 300 years ago, has acquired new
+importance in this century. Many scientists have contributed to it: 13
+of them have received Nobel Prizes for work directly bearing on the
+chemical and biological importance of phosphorus compounds. In
+chronological order, they are: Eduard Buchner, Albrecht Kossel, Otto
+Meyerhof, Arthur Harden, Hans von Euler-Chelpin, George de Hevesy, Carl
+F. Cori, Gerty T. Cori, Fritz Lipmann, Lord Alexander Todd, Arthur
+Kornberg, Severo Ochoa, and Melvin Calvin. The developers of industrial
+production and commercial utilization of phosphate compounds have had
+other rewards.
+
+Some impression of the continuing growth in this field[43] can be gained
+from the following data.
+
+PHOSPHATE ROCK
+
+annually "sold or used by producer" in the United States in million long
+tons (2,240 lbs.)
+
+    1880    0.2
+    1890    0.5
+    1900    1.5
+    1910    2.655
+    1920    4.104
+    1930    3.926
+    1940    4.003
+    1945    5.807
+    1950   11.114
+    1955   12.265
+    1955   (world: about 56)
+    1960   17.202
+    1962   19.060
+
+Sources: U.S. Bureau of the Census. _Historical Statistics of the United
+States 1789-1945_ (1949); _Statistical Abstract of the United States._
+
+ELEMENTAL PHOSPHORUS
+
+annually produced in the United States in short tons (2,000 lbs.)
+
+    1939     43,000
+    1944     85,679
+    1950    153,233
+    1956    312,200
+    1958    335,750
+    1959    366,350
+    1960    409,096
+    1961    430,617
+    1962    451,970
+
+Source: U.S. Department of Commerce.
+
+
+
+
+FOOTNOTES:
+
+
+[1] WILHELM HOMBERG, _Memoires Academie, 1666-1699_ (Paris, 1730), vol.
+10, under date of April 30, 1692, pp. 57-61.
+
+[2] FORTUNIO LICETUS, _Lithiophosphorus sive de lapide Bononiensi_
+(Venice, 1640).
+
+[3] Cited in PETER JOSEPH MACQUER _Chymisches Woerterbuch_, 2nd ed.
+(Leipzig: Weidmann, 1789), vol. 4, p. 508, footnote "c" as "Kletwich (de
+phosph. liqu. et solid. 1689, Thes. II)."
+
+[4] FERDINAND HOEFER, _Histoire de la Chimie_ (Paris, 1843), vol. 1, p.
+339.
+
+[5] G. W. VON LEIBNIZ, _Memoires Academie_ (Paris, 1682); _Akademie der
+Wissenschaften, Miscellanea Berolinensia_ (Berlin, 1710), vol. 1, p. 91.
+
+[6] JEAN HELLOT, _Memoires Academie 1737_ (Paris, 1766), under date of
+November 13, 1737, pp. 342-378.
+
+[7] MACQUER, op. cit. (footnote 3), p. 551.
+
+[8] A. S. MARGGRAF, _Akademie der Wissenschaften, Miscellanea
+Berolinensia_ (Berlin, 1743), vol. 7, 342 ff.; see also WILHELM OSTWALD
+_Klassiker der Exakten Naturwissenschaften_ (Leipzig: Engelmann, 1913),
+no. 187.
+
+[9] G. HANCKEWITZ, [Hankwitz], _Philosophical Transactions of the Royal
+Society of London_, 1724-1734, abridged (London, 1809), vol. 7, pp.
+596-602.
+
+[10] ANTOINE LAURENT LAVOISIER, "Sur la Combustion du Phosphore de
+Kunckel, Et sur la nature de l'acide qui resulte de cette Combustion,"
+_Memoires Academie 1777_, (Paris, 1780), pp. 65-78.
+
+[11] GUYTON DE MORVEAU and others, _Methode de Nomenclature Chimique_,
+Proposee par MM. de Morveau, Lavoisier, Bertholet, & de Fourcroy (Paris,
+1787), plate 9.
+
+[12] MACQUER, op. cit. (footnote 3), p. 513.
+
+[13] MARIE BOAS, _Robert Boyle and Seventeenth Century Chemistry_ (New
+York: Cambridge University Press, 1958), p. 226; see also WYNDHAM MILES,
+"The History of Dr. Brand's Phosphorus Elementarus," _Armed Forces
+Chemical Journal_ (November-December 1958), p. 25.
+
+[14] ARCHIBALD CLOW and NAN L. CLOW, _The Chemical Revolution_ (London:
+Batchworth Press, 1952), p. 451.
+
+[15] EMILE KOPP, _Comptes-rendus hebdomadaires des Seances de l'Academie
+des Sciences, Paris_ (1844), vol. 18, p. 871; WILHELM HITTORF, _Annalen
+der Chemie und Pharmazie_, suppl. to vol. 4, p. 37; ANTON SCHROeTTER,
+_Annales de Chimie et de Physique_, series 3, vol. 24 (1848), p. 406;
+see also Schroetter's report on "Phosphor und Zuendwaaren" in A. W. VON
+HOFMANN, _Bericht ueber die Entwicklung der Chemischen Industrie_
+(Braunschweig: Vieweg, 1875), pp. 219-246.
+
+[16] R. GLAUBER, _Furni Novi Philosphici_ (Amsterdam, 1649), vol. 2, pp.
+12 ff.
+
+[17] HERMANN SCHELENZ, _Geschichte der Pharmazie_ (Berlin: Springer,
+1904), p. 598.
+
+[18] J. PERSONNE, _Comptes-rendus ..._, Paris (1869), vol. 68, pp.
+543-546.
+
+[19] A. WURTZ, _Dictionnaire de Chimie_ (Paris, 1876), vol. 2, part 2,
+p. 951.
+
+[20] KARL W. SCHEELE, _Nachgelassene Briefe und Aufzeichnungen_, edit.
+A. E. Nordenskioeld (Stockholm: Norstedt, 1892), pp. 38, 144.
+
+[21] J. J. BERZELIUS, _Lehrbuch_, transl. F. Woehler (Dresden, 1827),
+vol. 3, part 1, p. 96.
+
+[22] THOMAS GRAHAM, _Philosophical Transactions of the Royal Society of
+London_ (1833), pp. 253-284.
+
+[23] JUSTUS LIEBIG'S _Annalen der Pharmacie_ (1838), vol. 26, p. 113 ff.
+
+[24] A. WURTZ, _Annales de Chimie et de Physique_, series 3, vol. 16
+(1846), p. 190.
+
+[25] CARROLL D. WRIGHT, _The Phosphate Industry in the United States_,
+sixth special report of the Commissioner of Labor (Washington, 1893).
+
+[26] J. STOKLASA, _Biochemischer Kreislauf des Phosphat-Ions im Boden,
+Centralblatt fuer Bakteriologie ..._ (Jena: Fischer, March 22, 1911),
+vol. 29, nos. 15-19.
+
+[27] N. T. GOBLEY, _Comptes-rendus_ ..., Paris (1845), vol. 21, p. 718.
+
+[28] A. WURTZ, _Comptes-rendus_ ..., Paris (1868), vol. 66, p. 772.
+
+[29] L. THUDICHUM, _Die chemische Constitution des Gehirns des Menschen
+und der Tiere_ (1901); see also H. WITTCOFF, THE PHOSPHATIDES (New York:
+Reinhold, 1951).
+
+[30] WILLIAM CROOKES, _British Association for the Advancement of
+Science, Reports_ (1887), sec. B, p. 573.
+
+[31] J. E. COURTOIS and A. LINO, _Progress in the Chemistry of Organic
+Natural Products_, edit. L. Zechmeister (Vienna: Springer Verlag, 1961),
+vol. 19, p. 316-373.
+
+[32] A. WURT, _Dictionnaire de Chimie_, supp. part 2, [n.d.] p. 1087; A.
+KOSSEL, _Zeitschrift fuer physiologische Chemie_, series 3 (1879), p.
+284.
+
+[33] ALEXANDER TODD, _Les Prix Nobel en 1957_ (Stockholm).
+
+[34] HANS VON EULER-CHELPIN, _Les Prix Nobel en 1929_ (Stockholm).
+
+[35] O. MEYERHOF and E. LUNDSGAARD, _Naturwissenschaften_ (Berlin,
+1930), vol. 18, pp. 330, 787.
+
+[36] K. LOHMANN, _Naturwissenschaften_ (Berlin, 1929), vol. 17, p. 624;
+C. H. FISKE and Y. SUBBAROW, _Science_ (Washington, 1929), vol. 70, p.
+381 f.
+
+[37] J. BRACHET, _Scientia, Revista di Scienza_ (1960), vol. 95, p. 119.
+
+[38] GEORGE DE HEVESY, _Les Prix Nobel en 1940_ (Stockholm). See also
+EDUARD FARBER, _Nobel Prize Winners in Chemistry_, 2nd ed. (New York:
+Schuman, 1963), p. 179.
+
+[39] See, e.g., _Chemical Week_, vol. 77 (September 3, 1955), p. 79 f.;
+J. BOLLE, _Chimie et Industrie_ (1960), vol. 83, p. 252.
+
+[40] W. LANGE, _Berichte der Deutschen Chemischen Gesellschaft_ (Berlin,
+1929), vol. 62, p. 793; vol. 65 (1932), p. 1598.
+
+[41] GERHARD SCHRADER, U.S. patent 2,336,302 of 1943 (priority in
+Germany, 1938); S. A. HALL and M. JACOBSON, _Industrial and Engineering
+Chemistry_ (1943), vol. 40, p. 694.
+
+[42] A. M. MATTSEN and others, _Journal of Agriculture and Food
+Chemistry_ (1955), vol. 3, p. 319.
+
+[43] JOHN B. VAN WAZER, _Phosphorus and its Compounds_, 2 vols.
+(vol. 1, _Chemistry_; vol. 2 _Technology, Biological Functions and
+Applications_, New York: Interscience, 1958, 1961.
+
+       *       *       *       *       *
+
+U.S. GOVERNMENT PRINTING OFFICE: 1965
+
+For sale by the Superintendent of Documents, U.S. Government Printing
+Office Washington, D.C. 20402--Price 25 cents
+
+
+
+
+INDEX
+
+
+Aristotle, 179
+
+
+Baeyer, Adolf, 193
+
+Bechil, Achild, 179
+
+Berthelot, Marcellin, 189
+
+Berzelius, Joens Jakob, 182
+
+Black and Bell, plant at Stratford, 182
+
+Boussingault, Jean Baptiste, 185
+
+Boyle, Robert, 178, 179
+
+Brand, H., 178, 179
+
+Buchner, Hans, 197, 200
+
+
+Calvin, Melvin, 200
+
+Casciarolo, Vicenzo, 179
+
+Chevreul, Michel, 189
+
+Cori, Carl F., 200
+
+Cori, Gerti T., 200
+
+Crookes, William, 192
+
+
+Davy, Sir Humphry, 185
+
+De Hevesy, George, 198, 200
+
+De la Vega, Garcilaso, 185
+
+De Saussure, Theodore, 185
+
+
+Euler-Chelpin, Hans von, 197, 200
+
+
+Fernelius, Jean, 179
+
+Feulgen, Robert, 193
+
+Fischer, Emil, 193
+
+
+Gahn, Johann Gottlieb, 182
+
+Gay-Lussac, Joseph Louis, 182
+
+Gobley, Nicolas Theodore, 191
+
+Graham, Thomas, 182, 183, 185
+
+
+Hankwitz, Gottfried, 180
+
+Harden, Arthur, 197, 200
+
+Hartmann, Immanuel Peter, 181
+
+Hellot, Jean, 180
+
+Henry II, King of France, 179
+
+Hittorf, Wilhelm, 181
+
+Hoefer, Ferdinand, 179
+
+Holmberg, Wilhelm, 178
+
+Hoppe-Seyler, Felix, 193
+
+Humboldt, Alexander von, 185
+
+Huygens, Christiaan, 179
+
+
+Incas, 185
+
+
+Kletwich, Johann Christopher, 179
+
+Koppe, Emile, 181
+
+Kornberg, Arthur, 200
+
+Kossel, Albrecht, 200
+
+Kraft, Johann Daniel, 179
+
+Kramer, Dr. ----, 181
+
+Kunckel, Johann, 179
+
+
+Lange, W., 199
+
+Lavoisier, Antoine Laurent, 181, 185
+
+Laws, John Bennet, 186
+
+Leibnitz, Gottfried Wilhelm von, 179
+
+Lennox, Charles, third Duke of Richmond, 185
+
+Leonhardi, Johann Gottfried, 179
+
+Levine, Phoebus Aaron Theodor, 193
+
+Liebig, Justus, 183, 185, 186
+
+Liebreich, Oscar, 191
+
+Lipmann, Fritz, 200
+
+London, E. S., 193
+
+
+Macquer, Peter Joseph, 180
+
+Marggraf, Andreas Sigismund, 180
+
+Meyerhof, Otto, 194, 200
+
+Miescher, Johann Friedrich, 192
+
+Muspratt, James, 186
+
+
+Nietzsche, Friedrich, 186, 187, 189
+
+
+Ochoa, Severo, 200
+
+
+Pelouze, Theophile Juste, 189
+
+
+Rouelle, Guillaume Francois, 181
+
+
+Scheele, Karl W., 182
+
+Schmiedeberg, Oswald, 193
+
+Schrader, Gerhard, 199
+
+Schroetter, Anton, 181
+
+Stoklasa, Julius, 186
+
+Strecker, Adolf Friedrich, 191
+
+
+Thudichum, Ludwig, 192
+
+Todd, Lord Alexander, 200
+
+
+Willm, Edmond, 182
+
+Willstaetter, Richard, 191
+
+Wurtz, Adolphe, 185, 191
+
+
+
+
+Transcriber's Notes
+
+
+The following typographical errors have been corrected:
+
+    Page 180 "_Abfaellen_, Vieweg, Braunschweig," - had "Viewig".
+    Page 188 "wires _d_ from the dynamo D" - had "dynano".
+    Page 191 "phosphate are attached, for example," - had "attached, For".
+    Page 192 "But phosphatides occur" - had "phosphatide soccur".
+    Page 193 "the nucleic acid from the thymus" - had "nucleidic".
+    Page 199 "acetylcholine esterase." - had "acetylcholin".
+    Page 200 "George de Hevesy, Carl F. Cori," - comma added after Hevesy.
+    Footnote [39] "See, e.g., _Chemical Week_, vol. 77" - had "See. e.g."
+    Index Entry: "Gahn, Johann Gottlieb, 182" - had "Gaehn"
+
+The spelling of "Bertholet" [Claude Louis Berthollet] is as given on the
+original title page of the work referenced in this paper.
+
+Inconsistent hyphenation of chemical names has been retained.
+
+
+
+
+
+End of the Project Gutenberg EBook of History of Phosphorus, by Eduard Farber
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