ONCE WOHLER REFUTED THE OLD VITAL FORCE THEORY, THERE WAS NO STOPPING THE CREATIVE INGENUITY OF THE ORGANIC CHEMISTS
UP TO
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a century before the founding of the AMERICAN CHEMICAL SOCIETY, there were very few organic compounds known. Acetic acid, alcohol, sugar, and soaps were familiar to ancient peoples, indigo and alizarin were used in dyeing by the Romans and Egyptians, and Tyrian purple by the Phoenicians, and in the sixteenth century benzoic and succinic acids were discovered. Then in the latter part of the eighteenth century, the Swedish chemist Scheele isolated several organic acids from natural sources-tartaric, lactic, hydrocyanic, citric, malic, oxalic, and gallic. He prepared mucic acid from lactose and obtained glycerol (“sweet oil”) from olive oil. Chemistry was awakening as a science and organic chemistry was arising as a vital part of it. Interest in organic compounds increased, as indicated by the isolation of a number of substances chiefly of biological origin. Lavoisier proved that many of them upon being burned gave carbon dioxide and water, which indicated that they contained carbon and hydrogen. The chemistry of carbon compounds was taking shape. I n the meantime, the strange theories of phlogiston and caloric were being disposed of. Then in 1828 Wohler prepared urea from ammonium cyanate and thus upset the theory that a “vital force” was necessary to produce organic compounds. As one writer put it, “Wohler stood upon the threshold of a new era in chemistry as he witnessed ‘the great tragedy of science, the slaying of a beautiful hypothesis by an ugly fact.’ ” Berzelius is usually credited with giving the name “organic” to these new substances, although there is evidence that von Schelling of Jena in 1798 originated the term. Berzelius fought a hopeless battle for his theory of electronegative and electropositive radicals. His theory was probably better than his evidence. Then there arose the theory of types, which was of great value in the development of the science. This concept continues to this day in what is now known as the structural theory. The idea of valence slowly developed from Dalton’s models, and in 1857 Kekul6 and Couper independently arrived a t the tetravalency of the carbon atom. A few years later, Kekul6 announced the great concept of the ring structure of benzene, and then (1874) van’t Hoff and Le Bel independently described the theory of the position of atoms in space-stereochemistry. Thus, a t the time of the founding of the AMERICAN CHEMICAL SOCIETY, organic chemists were already a t work isolating organic compounds, determining their structpres, studying their properties, and synthesizing known and new organic compounds. Chemical journals were expanding rapidly with detailed reports of their discoveries. It is no wonder that thoughtful American chemists were feeling the urge to establish their own society and their own journals. The first paper read a t the first regular meeting (May 4, 1876) of the Society after its foundation on April 6, 1876, was by Hermann Endemann, entitled “On the Determination of the Relative Effectiveness of Disinfectants.” The secretary noted that “the discussion of [the paper] closed a t a late hour, on which account the papers by P. Casamajor and I. Wale were laid over till the next meeting.” It was many years before time limits were
placed on the presentation of papers at A.C.S. meetings. At that same regular meeting there was adopted “Rule I. No vote of thanks shall be passed to any member of the Society for any paper or communication read before the Society.” In the next five meetings of the Society, June to October 1876, five papers were given on petroleum: “Kerosene Oil,” “Explosions and Method of Testing Petroleum Oil,” “Pennsylvania Petroleum,” “The Quantitative Determination of Naphtha in Crude Petroleum,” and “On Galician Ozokerite and Ceresine.” So organic chemistry got off to an auspicious start in the meetings of the Society, even though the programs might now be considered somewhat one-sided. Interest is often a product of contemporary happenings. The first paper printed in the first volume of the Journal of the American Chemical Society, 1879, related to analytical organic chemistry: “A Method for the Detection of Artificial or DextroGlucose in Cane Sugar, and the Exact Determination of Cane Sugar by the Polariscope,” by P. deP. Ricketts, Ph.D. The Crucial Years, 1876-1890. Organic chemistry, especially abroad, was moving forward rapidly. During this period, Emil Fischer prepared hydrazines and used them t o isolate and identify sugars as osazones. He also synthesized glucose. Friedel and Crafts perfected their synthesis of aromatic derivatives. Witt formulated his chromophore-auxochrome theory of color and gave new life to the work on dyestuffs. Baeyer synthesized indigo, proclaimed his strain theory, and did an enormous amount of work on the constitution of benzene. Tilden observed the polymerization of isoprene (from turpentine) into a rubberlike material. Victor Meyer isolated thiophene and also demonstrated the stereoisomerism of nitrogen. Kjeldahl published his method of determining nitrogen in organic substances. Laar described the “continued oscillation” of a hydrogen atom between two positions in certain molecules, naming the phenomenon ‘%automerism.” Claisen worked out syntheses from acetoacetic ester. Furthermore, Ladenburg carried out the f i s t synthesis of an alkaloid, d-coniine from a-picoline, and, of industrial interest, Chardonnet produced “artificial silk” from nitrated cotton. Cross and Bevan made a similar product by their viscose process. At first, scientific accomplishments in this country were not as striking as those abroad, but American organic chemists were making substantial progress. It must be remembered that the first graduate institution in which students of chemistry could obtain advanced instruction in this country, Johns Hopkins University, was not established until 1876. Work reported in the first four volumes of the Journal of the American Chemical Society covered, in addition to a wide range of analytical and inorganic subjects, organic articles on new dyestuffs, derivatives of toluene and phenanthrene, illuminating gas from wood, thiocarbanilide, heptylene from heptane (from Pinus sabiniani), tannic acid, crystalline dextrose, bone oil, and composition of elephant’s milk. Some of the organic work of this period was published in the American Chemical Journal, which was founded in 1879, the same year as the Journal of the American Chemical Society. For ex-
H. L. Fisher, National Research Council, Washington, D. C.
289
3.,C. asher
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INDUSTRIAL AND ENGINEERING CHEMISTRY
ample, the d merican Chemical Jour.nal contained papers on the discovery of “benzoic sulfinide” (saccharin) by Remsen and Fahlberg, Chittenden’s pioneer work in physiological chemistry, Oshorne’s on cryst’alline proteins, Conestock and Kleeberg’s on nitrogen and oxygen ethers of compounds containing the grouping --r\“CO--, contributions to the chemistry of camphor by R. A. Sove?, Stieglitz‘s JT-ork on imido wters, Kohlcr’s on unsaturation. and Dakin’s principle of p-oxidation in biochemical transformations. After this journal reached its fiftiet.h volume, it was merged with the Journal o j the / l i n c ~ i c mChemical Society in 1914. Abroad, Emil Fischrr continued to make historic contributions to organic chemistry. Aft,er his rcmarkable work on the sugars, he cleared up much of the chemistry of t,he purines and then laid the foundation for the chemistry of the proteins. Thiele stated his partial valence theory and its applications. Grignard discovered the most, prolific method of synthesizing organic compounds, the Grignard rcaction. Werner proposed his coordination theory, Sabatier gave the chemical world the cat,alytic method of hydrogenation, and Walden discovered the stereochemical inversion that, carries his name. In this country, the great organic experimenter A-ef ttccomplished an enormous amount of work on the course of many chemical reactions, including t,hose to demonstrate his theory on the existenoe of divalcnt carbon. Takamine isolated adrenaline, Gomberg discovered triphenylmet,hyl and established that carbon exists in a t,rivalent form (explained more recently by the theory of resonance). Arthur Michael accomplished the fist synthesis of a glycoside (salicin) (1883) and made many investigations beariiig on the fundamental laws and theory of organic chemistry. THE S E C O N D TWENTY-FIVE YEARS OF THE A.C.S., 1901-1996
During this period, organic chemistry grew rapidly, especially after World War I. This growth can be measured, in part, by romparing the number of students who received the degree of
Vol. 43. No. 2
Ph.l>. In the four years 1898 to 1901, 113 students were aiwrtied this degree in chemistry, and of these only 9 were in orgaiiir chemistry, an average of 2.25 a year. However, in the s o h i d year 1925-26, 256 student,s were awarded this degree in c~ht~mistry, and of these 98 were in organic chemistry. When Sviititt Arrhenius was awarded his doctor’s degxe at Uppsala in 1884, a laurel wreath was placed on his head and a cannon boomed the advent of another doctor of philosophy. If this custom had becn followed in this country when organic and other chemish ~verc being turned out in large quantities as doctors of philosophy, Boine of our universities at, graduation time would have been noisy places, indeed. The chemistry departments oi prominent universities were improving or building new laboratories, and students with graduate training had little difficulty in obtaiqing positions as teachers or research chemists in industry. Organic chemists were doing a great deal of research i i i the synthesis of compounds and some mere even criticized for “just filling up Beilstein.” However, these Beilstein synthetic conipounds very soon became of wonderful service, as organic and physical chemists applied the principles of physical chenlist.ry to obtain an understanding of type reactions and to determine the structure of compounds and their rates of reaction. Industrial organic chemistry was expanding rapidly, and organic chemists helped much to bring compounds out of the test-tube stage into the plant, especially during the war when German supplies were cut off. Dyestuffs, pharmaceuticals, cosmetics, solvents, photographic chemicals, compounds for the rubber and paint and vwnish industries-all were in grea,t demand during World War. I. Organic chemistry boomed. In this country, chemists had depended almost entirely on &rmany for their supplies, especially organic chemicals. When the war halted these shipments, C. G. Derick of the Department of Organic Chemistry a t the University of Illinois organized a vacation class in 1916 to prepare organic chemicals in somewhat, larger quantities than those ordinarily synthesized in the regular laboratory courses. The chemicals prepared in this way were used by the department the following year. He left university work shortly afterwards, and Roger Adams, his successor, took over and enlarged the work and thus helped many organic chemists at, Illinois and other institutions. In order to make the chemicals available to a wider group, a central clearinghouse was needed, and E. E. Reid and the writer were appointed by the Division of Organic Chemistry as a committee of two to find a solution to the problem. While they were beginning their work and visit,iiip possible interested companies, C. E. K. Mees of the Eastman Kodak Co. announced at a meeting of the division in 1918 that his company had decided to hegin the preparation of organic chemicals, to purify chemicals obtained from industrial chemical. companies, and to supply the American market. This service was of great benefit to organic research workers and has continued i o the present time. Out of the work a t the University of Illinois grew the publication of detailed practical methoda of preparing organic compounds, f i s t in a series of pamphlets, then in those exceedingly useful annual volumes of “Organic Syntheses.” Again, let us take a look a t the work of organic chemistma abroad. Harries discovered the ozonides and their value as a means of locating double bonds. By this method, E-Iarries unraveled the chemical nature of the rubber hydrocarbon. At the Eighth International Congress of Applied Chemistry in New York in 1912, Perkin discussed, with demonstrations, the work of English chemists on the synthesis of rubberlike products from butadiene and isoprene. In 1915 Ostromislensky published his famous work on the synthesis of butadiene and isoprene and their polymerization to synthetic rubbers. Willstatter did his notable. work on the constitution of chlorophyll and the anthocynris; P. Ehrlich prepared salvarsan; Pregl performed his important
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iervice for organic chemists by perfecting methods of micromalysis; Ruzicka and also Butenandt synthesized hormones; Haworth formulated sugars as chiefly 8-oxides or pyranose derivatives; Ruzicka synthesized multimembered carbon rings; and Harington synthesized thyroxin, which had been isolated ten years before by Kendall in this country. And in this country, P. A. Levene at the Rockefeller Institute for Medical Research solved the riddle of the nucleic acids (the Brst paper on organic chemistry heard by the writer, in New York, 1910) and other biologically important substances; Marston T. Bogert at Columbia University synthesized many substances in the fields of nitrogen heterocycles, dyestuffs, and terpenes; Treat B. Johnson at Yale University similarly synthesized numerous compounds in the pyrimidine and purine fields; C. S. Hudson of the Bureau of Chemistry of the U. S. Department of Agriculture announced his rules of isorotation, outlined the configuration of sugars (including a- and p-isomers), and synthesized many sugar derivatives; E. P. Kohler of Harvard University advanced the theoretical understanding of addition reactions; W. A. Noyes of the University of Illinois worked on the problem of positive and negative valences; and Julius Stieglitz of the ZJniversity of Chicago not only contributed to our knowledge of molecular rearrangements but also applied physicochemical methods to the solution of other problems in organic chemistry. S. P. Mulliken of Massachusetts Institute of Technology brought out remarkable books on the identification of organic compounds. This series has had a usefulness and influence f a r greater than originally expected. In 1915 W. L. Bragg came to America from England and gave lectures on the structure of compounds as determined by x-ray analysis. His lectures and demonstrations were particularly interesting because they confirmed many conclusions previously reached by organic chemists, especially with regard to the cyclic structure of crystalline benzene and naphthalene. Division of Organic Chemistry. Up to and through the thirtieth meeting of the Society held in Providence, R. I., June 21 to 23, 1904, there were only general sessions a t each A.C.S. meeting. I n other words, there was only one program which occupied one or more sessions. Many members were becoming restive: an industrial chemist was not interested in listening to papers on biological, organic, or physical chemistry, and vice versa. At the meeting of the Council a t Providence, it was moved that “it is the sense of the Council that a t the Philadelphia meeting the Society should meet in part in general session and in part in sections.” Therefore, a t the Philadelphia meeting, December 28 to 31, 1904, according to the record in the Proceedings, there was a general session and then “the general session adjourned and the Society met in sections a t 11:30 A.M. and again at 2:30 P.M.” Papers were presented in five sections-Physical Chemistry ; Agricultural, Sanitary, and Physiological Chemistry; Industrial Chemistry; Inorganic Chemistry; and Organic Chemistry. James F. Norris was chairman of the Organic Section. The practice of meeting in sections evidently was successful, because the Society continued to meet in general session followed by sectional sessions. The chairmen of these Organic Sections were Marston T. Bogert, Buffalo, June 22 to 24, 1905; Charles F. Mabery, New Orleans, December 29 to January 2, 1905-06; G . €3. Frankforter, Ithaca, June 28 to 30, 1906; A. S. Wheeler, New York, December 27 to 31, 1906; J. Bishop Tingle, Toronto, June 27 to 29, 1907; Julius Stieglitz, Chicago, December 31 to January 3, 1907-08; Wm. McPherson, New Haven, June 30 to July 2, 1908; and S. F. Acree, Baltimore, December 29 to January 1, 1908-09. At the meeting of the Organic Section, December 30, 1908, it was voted to petition the Council of the Society for a Division of Organic Chemistry. The Council having granted this petition, the division was given a temporary organization, December 31, by the election for one year of a chairman, Richard S. Curtiss, and a vice chairman and secretary, Ralph H. McKee. The
Corner of Baekeland’s laboratory in Yonkers, N . Y . , complete with distillation apparatus, pots, and pans (1910)
Modern organic laboratory at Reltsville Research Center, where chernist i s at work on new insecticide
The intricacies of present-day organic chemicals manufacture are illustrated by Merclc’s ribojlavin plant 291
Division of Organic Chemistry met officially as dimion a t the Detroit meeting of the Society, June 29 to July 2, 1909. At the same time President Whitney appointed J. F. Norris, S.P. Mulliken, and Wm. McPherson as a committee to report on the constitutionality of the bylaws of the division, and these were shortly afterward passed by the Council. At this point, it is debirable to quote from Secretary Parsuns’ history of the divisions in the Golden Jubilee Number of the Jozcrna 1.
Research worker at the iMellon Institute delves into a complex problem in organic chemistry
Shell Chemical’s giant synthetic glycerol plant ut Houston, Tex., uses petroleum gas as raw material
I n no country but our own have the pure and applied chriiiicai scientists been able to work together in one organization with mutual appreciation and without serious jealousies. This is one of the chief s6crets of the success of the AMERICAN. CaI:iiI(xb SOCIETY, which was brought about through the wise foresight oi President Bogert, who clearly foresaw that the Society was likclg to disintegrate unless some method was devised by which specialists in various branches of chemistry might gather t o g d i e r in essentially autonomous meetings. Accordingly, he inaugurated the divisional system, establishing first the Division of Industrial and Engineering Chemistry, followed gradually by others No wiser step has been taken in the dociety’s development than the organization of the divisional system. More Chemistry. Beforr leaving this second 25-year period, it would be well to mention a few more advances in chcmistr~ that occurred during that interval. War chemicals, spwifirailv mustard gas, were developed and put into large scale production Two other compounds, chlorodihydrophenarszine (adamsite) and chlorovinyldichloroarsine (lewisite), were developed by arid named after two university professors, Roger Adams and W. 1,ce Lewis. It seems odd that it fell to the lot of two gentlemen of the classroom to develop two such obnoxious war chemicals, but “C’est la guerre.” It was also in this general period that Thomas Midgley, Jr., who was trained as a civil engineer, discovered the use of tetraethyllead as an antiknock compound. This chemical is important riot only because of its effectiveness but also because after over 25 years it Btill is paramount in its field and evidently has no cornpetition. Its discovery was the result of a highly systematic search for organometallic compounds that are derivatives of elements in a particular part of the periodic system. J. B. Conant determined oxidation-reduction potentials, especially in the quinone group, and studied the relation between structure and the rate of reaction of certain organic compounds. R. R. Renshaw increased our knowledge of organic oniuni compounds. F. C. Whitmore prepared organomercuric compounds. and Henry Gilman improved methods of using the Grignard reaction. G. N. Lewis paid a real tribute to the work of organic chemists when he wrote, “Structural organic chemistry, although developed without mathematics, except of the most elementary sort, is one of the very greatest of scientific achievements.. . It is this system of structural chemistry that served chiefly as my bask n-hen I advanced my theory of valence.” Irving Langniuir developed Lewis’ theory further emphasizing the importance of electron octets in the basic mechanism of chemical reactions. Langmuir also demonstrated the physical condition of long-chain acids and soaps on the surface of water with the hydrophilic carboxyl and the corresponding salt in the water and the hydrocarbon chains extending outward from the surface in a monomolecular layer, the thickness of which corresponds to the number of carbon atoms in the chain. T H E T H I R D W E N T Y - F I V E Y E A R S OF THE A.C.S.,
192&1951
Organic chemistry covers many fields, and naturally i t became the mother of several offspring which evolved into divisions of the Society. These are the Divisions of Biological, Cellulose, Gas and Fuel, High Polymer, Industrial and Engineering (in part), Medicinal, Paint, Varnish and Plastics, Petroleum, Rubber, and Sugar Chemistry. Accordingly, the nanies of many investigatori-
A portion of the ethylene unit at the Jeferson Chemical Co. near Port Neches, Tex. 292
February 1951
INDUSTRIAL AND ENGINEERING CHEMISTRY
293
and their work are found in the histories of these special branches known for the study of compounds. Many a mess went down instead of in this history of the mother science. the sink or into the waste jar because it seemed too difficult to Science is considered to be impersonal by some people, but to handle. As time went on and organic chemistry came into its the writer it is very personal. Who can think of induced electric o m in this country, chemists turned toward some of the ‘kegcurrents without thinking of Faraday, of the law of gravitation lected” chemicals and also to such cheap raw materials as natural without Newton, of penicillin without Fleming, of triphenylgas and petroleum, alcohol, and other products of fermentation. methyl without Gombexg? It is difficult, therefore, to discuss Thus aliphatic chemistry grew and later far overshadowed arothe advancements in chemistry witlrout a t least mentioning the matic chemistry. chemists who made them. However, it must be said that in the National Symposium of Organic Chemistry. At the beginpast 25 years there have been many changes in scientific methods ning of this third 25-year period, American organic chemists beand in the methods of sciengan - to feel that they wanted tists. Now laboratory work more time for meetings than Officers of the Division of Organic Chemistry, 1910-1951 was provided a t the two is done much more than ever in groups. Modern apparanational meetings of the SoYear Chairman Secretary tus and group efforts have ciety for the discussion of made it possible to produce 1910 E. C. Franklin R. H. McKee papers and organic problems wonderful results in a short 1911 G. B. Frankforter William J. Hale in general. To fill this need, time. Cooperation is the 1912 Treat B. Johnson William 5. Hale the National Symposium of watchword. A biochemist 1913 Treat B. Johnson William J. Hale Organic Chemistry was orB. F. Allen C. G. Derick in Hungary, Szent-Gyorgi, 1914 ganized. The first meeting C. G. Derick was held in Rochester, N. Y., isolates a very large and 1915 B. F. Allen unheard-of amount of vita1916 C. G. Derick Harry L. Fisher December 29 to 31, 1925, min C and generously sends 1917 J. R. Bailey under the chairmanship of Harry L. Fisher 1918 William J. Hale i t to an organic chemist in Harry L. Fisher Marston T. Bogert. About L. W. Jones England, Haworth, who, with 1919 Harry L. Fisher 175 members were present. the assistance of a group of 1920 E. E. Reid Roger Adams The meeting was so successful H. T. Clarke trained amciates, determines 1921 Roger Adams that the symposia were con1922 H. T. Clarke Frank C. Whitmore tinued every other year a t its structure and then synthesizes i t a l l in the matter of months.
1923 1924
Frank C. Whitmore R. R. Renshaw
R. R . Renshaw
What are some of these differences in laboratory apparatus and methods? Even
1925 1926 1927 1928
J. A. Nieuwland Marston T. Bogert
Frank Frank Frank Frank
J. A. Nieuwland C. Whitmore C. Whitmore C. Whitmore C. Whitmore
about the same time until the ninth program in 1941, after which no more were held until 1947 because of the war. After the first program, the speakers a t the symposia were chosen by ballot from lists proposed by the membership of the division and its executive committee. Usually about fifteen papers were presented. Attendance quickly doubled and then almost trebled, reaching 488 a t the ninth meeting. The tenth symposium was held in Boston, June 12 to 14, 1947, and the eleventh in Madison, Wis., June 20 to 22, 1949. It seems worth while t o mention some of the papers given a t these symposia because they indicate the type of chemical work carried out and the fields of the authors. Several Nichols and Willard Gibbs medalists were also among those who gave papers.
F. B. Dains William Lloyd Evans half a century ago, there was no borosilicate labora1929 E. C. Franklin Frank C. Whitmore Arthur C. J. Whitmore Hill 1930 Frank tory glassware, no or very little silica apparatus, no 1931 James B. Conant Arthur J. Hill glass equipment with stand1932 Homer Adkins Arthur J. Hill 1933 C. S. Marvel ard-taper ground-glass joints, Arthur J. Hill 1934 Claude S. Hudson no simple cheap vacuum Arthur J. Hill 1935 Arthur J. Hill pumps, no molecular stills, Ralph L. Shriner Ralph L. Shriner no stainless steel, no pH 1936 Henry Gilman 1937 L. C. Raiford Ralph L. Shriner meters, no this, no that. 1938 Lyndon F. Small Ralph L. Shriner Microanalytical methods 1939 Werner E. Bachmann Ralph L. Shriner were not yet devised to speed 1940 Cliff S. Hamilton Arthur C. Cope up work on very small quantities of material. There were 1941 Nathan L. Drake Arthur C. Cope 1942 Lee I. Smith Arthur C. Cope practially no machines for Arthur C. Cope 1943 Louis F. Fieser making rapid calculations. 1944 Ralph L. Shriner Arthur C. Cope How then can all the S. M. McElvain Ralph W. Bost 1945 chemical achievements of S.M. McElvain Ralph W. Bost 1946 the past 25 years be appraised 1947 Arthur C. Cope Ralph W. Bost and how recorded in the brief 1948 Paul D. Bartlett Ralph W. Bost space allotted? The problem 1949 William G. Young Ralph W. Bost is difficult. About all the 1950 Ralph W. Bost Nelson J. Leonard writer can’do is to make a Nelson J. Leonard 1951 William S. Johnson survey and try to pick out what appears to him to be the Wallace H. Carothers. “Polymerization, with Special Reference to the Polyesters.” high spots of the American scene. These will appear differently t o C. S. Marvel. “Hexa-Substituted Ethanes Containing Acetydifferent people, and the author will be criticized whatever malene Groups” and “Some Reactions of Vinylacetylene and the terial he chooses. Also, the selection will depend partly on his Synthetic Rubber program.” fallibility as a human being and upon the course of his life and F. C. Whitmore. “Intramolecular Rearrangements” and “The contacts. Mechanism of the Polymerization of Olefins.” E. C. Britton. “The Hydrolysis of Aromatic Compounds.” In the first 25 years of the Society, organic chemistry was conL.- F. Fieser. “Phenanthrene Derivatives Related to Natural arocerned laraelv with benzene and its derivatives-namelv. - Yroducts. matic chemistry. Some of the types studied had complicated Vincent du Vigneaud. “The Hormones Challenging the orstructures, but, because they usually crystallized well and could be ganic Chemist.” readily purified, they lent themselves to the processes then R. R. Williams. “Chemistry of Thiamine.” “
I
(1931), “Organic Chemistry in Biological Problems” ; Ed%a d C. Franklin (1932), “Ammonia System of Compounds”; Richard Willstiitter (1933), “Modern Enzyme Chemistry”; Roger Adam< (1936), ‘Catalysis and Stereochemistry of Diphenyl Derivatives”, Robert R. Williams (1938), “Vitamin B?’; Vladimir N. Ipatieff (1940), “Catalysis and High Pressure Synthesis”; Edward A. Doisy (1941),‘‘Hormones and Vitamin E(”; Thomas Midglry, Jr. (1942), “Tetraethyllead and Fluoro Compounds”; George. 0. Curme, Jr. (1944), “Synthetic Aliphatic Chemicals”; Frank C Whitmore (1945), “Molecular Rearrangements”, Wendell M. Stanley (1947), “Chemical Studies on Viruses”; Carl S Marvel (1950), “Polymer Chemistry.” From programs of the Organic Division the following irtdicatn~ the progress of our science in this country. The order ih chiefl\ chronological. R. H. Kienle. “The Polyhydric Alcohol-Polyhydric Acid Reaction. I. Glycerol-Phthalic Anhydride.” T. Midgley, Jr., and A. L. Henne. “Organic Fluorides aa Refrigerants.” One of these was demonstrated with the characteristically superb showmanship of the senior author. F. 0. Rice. “The Thermal Decomposition of Organic Coinpounds into Free Radicals.” H. T. Clarke. “Vitamin BI. The Sulfur-Containing Moiety I ’ L. G. S. Brooker. “Cyanin Dyes.” R. C. Elderfield and W. A. Jacobs. “The Structure of the Cardiac liglucones.” M. S. Kharasch. ‘ I ‘Normal’ and ‘Abnormal’ Addit,ions of HBr to Ethylene Derivatives.” Lee Irvin Smith. “Studies on Vitamin E, the Structure and Synthesis of a-Tocopherol.” Roger J. Williams. “Present Status of the Chemistry of Pantothenic Acid.”
Department of Agriculture pilot plant at Peoria, Ill., testing new processes for making alcohol ,from f a r m products E. A. Doisy. “Vitamin IC. Assay, Isolation, Constitution, and Synthetic Compounds.” Rudolph Schoenheimer. “Chemical Reactions of Constituents of Kormal Animals Studied with Isotopes.” Karl Folkers. “Chemistry of Vitamin Be.” At the Organic Symposium in Rochester, 1936, announcement was made that the division would sponsor a new publication, Journal of Organic Chemistry. A few words more about the Orgaiiir Division. At the beginning, each secretary held office for two years, then there was one three-year period, and a four-year period, and starting with 1925 the secretaries have been elected to serve for five years each. Chairmen of meetings always had difficulties in keeping some speakers from taking too much time. The officers of the division attempted to solve the problem by the use of an alarm clock, set to give a 2- or &minute warning. It helped, but did not always solve the problem. Sieuwland, who worhed in acetylene chemistry and often had explosions in his laboratory, never got used to the alarm, when he n-as secretary. He always jumped a t the sound, even when he was looking a t the face of the clock. Later, scheduled programs did solve the problem of overtime speakers. The first joint session of the division with other A.C.S. divisions was held a t Milwaukee, September 5 to 9, 1938. There were several joint sessions with the High Polymer Forum, beginning a t Atlantic City, April 8 to 16, 1946, and through the Kew York meeting, September 15 to 19, 1947. At Chicago, April 19 to 23, 1948, there was one double meeting of the division-that is, two concurrent sessions; another double meeting a t Atlantic) City, September 18 to 23, 1949; four concurrent seesions a t Philadelphia, April 9 to 13, 1950; and five concurrent sessions a t Chicago September 3 to 8, 1950. At this last mccting, 165 papers were read-the largest number on record. Nichols Medalists. Ten organir rbemists received Xchols medal awards, 1926-50: Roger hdanis (1927) for his work on “Acids of Chaulmoogra Oil”; he also did much work on a platinum catalyst for hydrogenation, 2nd on alkaloids, eipecially those of marihuana and hashish; J. B. Conant (1932), “Chemistry of Chlorophyll”; J. A. Nieuwland 11935), “Basic Research on Unsaturated Hydrocarbons”; Frank C Whitmore (1937). “Metallo-organic Compounds, and Polymerization”; P. A. Levene (1938), “Optical Activity”; John &I. Selson (1940), “Oxidases and Crystalline Tyrosinase;” C. S. Marvel (1944), “Polymers of SOz-OIefins and Vinyl Polymerization”; Vincent duVigneaud (1945), “Biotin”; William M. Stanley (1946). “Chemistry of Viruses”; and Oskar Wintersteiner ( I 950), “Steroid Hormones and Antibiotics.” Willard Gibbs Medalists. Twelve American and t!To foreign organic chemists received Willard Gibbs medal awards, 1926-50: Sir James C. Irvine (1926), “Structure of Carbohydrates”; Claude S. Hudson (1929), “Researches on Sugars”; P. A. Levene
Mention is also made of hydrogenation and hydrogenolysib with Raney nickel and copper chromite catalysts by Homer Adkins, study of allylic rearrangements by A. C. Cope, the nitration of aliphatic hydrocarbons by H. B. Haw, and the synthesis of quinotoxine by R. B. Woodward, who thus completed the long-awaitjed synthesis of the famous alkaloid, quinine. Using heavy oxygen, Harold Urey established the Course of esterification, showing that the oxygen in the water formed comes from the hydroxyl in the carboxyl group, a mechanism that had been indicated by li;. F: Reid long before in his work on mercaptans and thio acids. W. E. Bachmann synthesized phenanthrene compounds and related substances. Paul D. Bartlett used physicochemical methods in studies of organic reactions, including rearrangements, and the polvmerization of allylic compounds. R. C. Fuson studied vinylation. C. D. Hurd pyrolyzed organic compounds and indicated the course of decomposition. John R. Johnson synthesized antibiotics and highly unsaturated compounds. 8 M. McElvain made manv ketene acetals. A. A. Morton pointed out the relative acidities of hydrocarbons by reactions of their sodium derivatives and discovered a catalytic method of polymerizing diene hydrocarbons to rubberlike products. Syntheses from carbon monoxide and hydrogen, cracking of hydrocarbons, alkylation and isomerization of hydrocarbona (V. N. Ipatieff), polymerization of several types of organic winpounds, and the great synthetic rubber program, sulfa drugs, antimalarials, the use of isotopes in ferreting out the mechanism of organic reactions, hydrogen bonding, resonance, ultraviolet and infrared absorption phenomena and their interpretations the list of wonderful accomplishments goes on and on. In a way, it brings to mind a statement said to have been made by Gmi.lin when he was trying to complete his chemical dictionary. He wrote to Liebig in frustration: “For heaven’s sake, please stop your work until I get my dictionary published.” However, there is no stopping and there is no end. The writer likes to think of a remark made by P. A. Levrne at the close of a lecture on the chemistry of the sphingomyelins. “When we know all about the structure of all the substances in the human body and how they react, then there will still remain the riddle of life itself.” 294
