314 IV. WAXES, HIGHER ALCOHOLS, ETC. 



to a recent French report, ^'^ oleyl alcohol in 95% purity can be produced 

 by a modification of the above procedure. Sodium amalgam has been 

 recommended as the reduction agent. ^* 



Another highly successful commercial method for the synthesis of the 

 higher alcohols is the use of high-pressure catalytic processes as developed 

 both in Europe^^"^^ and in the United States.^* ~^^ The catalysts employed 

 include copper chromite,™ nickel or copper carbonate, ^^ or copper or chro- 

 mium oxides,^ ^ while the pressures range between 100 and 220 atmospheres 

 at temperatures of 200-300 °C. The catalysts ordinarily employed for 

 hydrogenation of the ethylenic bonds in the hydrogenation of fats, namely 

 nickel or cobalt, are unsatisfactory for the production of alcohols, since 

 hydrocarbons are the final products. High-pressure hydrogenation is 

 presumably the result of the independent discoveries made almost simul- 

 taneously by a large number of different workers. ^^•'''"^^ The first com- 

 mercial application of this process^^ was by the Deutsche-Hydrierwerke, 

 A.-G., at Berlin-Charlottenburg in 1927. In the United States,^8.79 the 

 method has been used by the E. I. du Pont de Nemours & Company, Inc., 

 since 1933. 



Prins^" obtained better yields of alcohols by a modification of the Bou- 

 veault-Blanc procedure. This involves the solution of the ester in ether 

 and placing the ethereal solution over aqueous sodium acetate. Sodium 

 strips and acetic acid are dropped in slowly while the ether layer is main- 

 s' Anonymous, Bull. mens. inst. technique eludes, recherches corps gras, No. 9, 3-9 

 (1947). Cited by M. L. Kastens and H. Peddicord, Ind. Eng. Chem., 41, 446 (1949). 

 6^ S. Shikata and Y. Inoue, U. S. Patent No. 2,263,195 (Nov. 18, 1941). 

 « A. F. Kertress, /. Soc. Dyers Colourists, 1,8, 7-9 (1932). 



66 W. Nermann, Z. angew. Chem., 44, 714-717 (1931). 



67 W. Schrauth, O. Schenck, and K. Stickdorn, Ber., B64, 1314-1318 (1931). 



68 R. Adams and C. S. Marvel, Univ. III. Bull., 20 [8], 54 (1922). Cited by M. L. 

 Kastens and H. Peddicord, Ind. Eng. Chem., 41, 438 (1949). 



69 H. Adkins and R. Cramer, J. Am. Chem. Soc, 52, 4349-4358 (1930). 

 ™ H. Adkins and R. Conner, J. Am. Chem. Soc., 53, 1091-1095 (1931). 



'1 H. Adkins and K. Folkers, /. Am. Chem. Soc, 53, 1095-1097 (1931). K. Folkers 

 and H. Adkins, ibid., 54, 1145-1154 (1932). H. Adkins, B. Wojcik, and L. W. Covert. 

 ibid., 55, 1669-1676 (1933). 



" H. Adkins, Reactions of Hydrogen, Univ. Wisconsin Press, Madison, 1937, p. 97. 



" R. Oda, J. Soc. Chem. Ind. Japan, 35, suppl., 349-352 (1932); Chem. Al)st., 26, 

 5544 (1932). 



"» O. Schmidt, Ber., B64, 2051-2053 (1931). 



'5 W. Schrauth, Ber., B65, 93-95 (1935). 



'6 S. Ueno and S. Ueda, J. Soc. Chem. Ind. Japan, 38, suppl., 482-486 (1935); Chem. 

 Absl.,29, 8371 (1935). 



" M. Briscoe, Chem. Trade J., 90, 76-78 (1932). 



™ W. A. Lazier. U. S. Patent Nos. 1,746,783 (Feb. 11, 1930); 1,839,974 (Jan. 5, 1932); 

 1,964,000 (June 26, 1934); 1,984,884 (Dec. 18, 1934); 2,079,414 (May 4, 1937); 2,109,- 

 844 (Mar. 1, 1938). 



" P. L. Salzberg, U. S. Patent Nos. 2,089,433 (Aug. 10, 1937); 2,129,507 (Sept. 6, 

 1938). 



8" IT, J. Prins, Bee trav. chim.., 42, 1 050-1 052 (1923). 



