EDWARD FARBER Washington, D. C.
Tm
birthday of glycol is March 24, 1856, the day when Adolphe Wurtz (1817-84) first prepared it (1). He converted ethylene into its iodide, which Faraday had discovered, and mixed it with two equivalents of silver acetate. A rather violent reaction occurred, and among its products was the new substance. Wurtz had predicted its existence as the missing link between alcohol and glycerine, which M. Berthelot had shown to he a three-atom alcohol (3). The basis for an explanation was the theory of types. Alexander W. Williamson (1824-1904) had found this theory so helpful that he said, "In the theory of types we owe to M. Dumas an idea which has already been the vehicle of many an important discovery in science" (5). The composition of organic substances was thus derived from simple and multiple molecules of water. Wurtz used the atomic weights of six for carbon and eight for oxygen when he wrote as follo~m:
C2H40 ethylene oxide
neurine base
cal with the natural one (7). The reactions which Adolf Baeyer had found with natural neurine also orcurred with the synthetized substance. Thus, the original discovery of the predicted twoatom alcohol had led Wurtz into a wide field which extended from the inorganic to the biochemical. Yet it took a long time before chemical industry became interested in this field. At the beginning of the first World War, Friedrich Bergius (1884-1949) advocated the creation of an industrial ethylene chemistry, hut this was received with great scepticism. The scarcity of glycerine during the war stimulated a small production of glycol as a replacement. Th. Goldschmidt A. G. put it on the market for use in cosmetics. Otherwise in 1919, glycol was still only listed as arawmaterial"for scientificpreparations and therapeutically valuable substances" (8). alcohol nlvrerine -alseal . -. At that time, however, work on glycol and ethylene He combined the first part of the name glycerine nith oxide had been started by George 0. Curme, Jr., a t the the last of alcohol to name his new substance. He Mellon Institute, and in 1925, Carbide and Carbon proved its constitution by oxidation to glycolic and Chemicals Company, a division of Union Carbide and oxalic acids, and built up the series of homologues: Carbon, put the first American glycol on the market. propyl-, hutyl-, and amyl-glycol (1857-58). He could Ethylene oxide, made by direct oxidation of ethylene then explain the nature of "the oil of the Dutch chem- which Wurtz had thought impossible, made its debut ists" (1795). It was a chloride that bore the same re- in 1931. Now the production of ethylene oxide is estilationship to glycol as the long known ethyl chloride mated a t 425,000 tons in 1955, with many companies did to ethyl alcohol (4). c6ntrihuting to the large production of glycols, mainly The reaction of the "Dutch oil" with potassium hy- ethylene glycol. The antifreeze market consumed droxide gave him ethylene oxide, a highly reactive iso- about 200,000 tons of this glycol in 1954, and about mer of acetaldehyde. With water, ethylene oxide forms 50,000 tons of the oxide mere converted into nonionic not only glycol, hut also di-ethylenic alcohol and the surfactants (9). corresponding tri- and tetra-ethylenic alcohols. This was of great general interest to Wurtz. Several years LITERATURE CITED before, he had published a study on "A series of or(1) WWRTZ, A., Compt. m d . , 43, 199 (1856); see A. W., VON ganic alcalies, homologues of ammonia" (5). I n it he HOFMANN, Z U EPinne~ung ~ an uorangerangene Freunde, 3 , described methyl- and ethyl-amide as the homologues of 349 (1888). ammonia, the "hydramide." I n ethylene oxide he (2) BERTHELOT, M., Compt. rend., 37, 348 (1853). A. W.. C h m . Soe. London.. 4.. 354 (1852. from . . WILLIAMSON. found another "link" t o inorganic chemistry. The (3) ~hem.'~azet& of 1851). poly-ethylenic alcohols (poly-ethylene-glycols) are an- (4) W the U R Top. ~ cit., 45, 228 (1857). alogues t o the poly-silicates and poly-stannates! (5) Ibid., 28, 223 (1849); see LEICESTER, HENRYM., AND HER"There is but one chemistry" (6). BERT S. KLICKSTEIN, "A Source Book in Chemistry," McGraw-Hill Book Co., Ino., New York, 1952, p. 362. Ethylene oxide also combined with ammonia and amines, leading him back to his old preoccupation with (6) WWTZ, Chem. Soc. London, 15,406 (1862). Ibid., Compt. rend., 66, 772 (1868). "organic alcalies." Of particular interest among these (7) (8) ULLMANN, F., EnzyklopMze, 6, 290 (1919). mas neurine. The artificial neurine which he obtained (8) JOSLIN, R. M., AND A. B. STEELE,Chear. Eny. News, 33, 5311 (1955). from ethylene oxide and trimethylamine proved identi-
