Summary
The two commercially important processes for the production of fatty alcohols (sodium reduction and hydrogenolysis) have been reviewed with respect to operations, types of alcohols obtainable, relative economics, properties and uses of the fatty alchols.
The sodium-reduction process is applicable to the reduction of saturated as well as unsaturated esters, and in the latter case the unsaturation of the raw materials is preserved in the product alcohols. Hydrogenolysis, on the other hand, produces predominantly saturated alcohols, regardless of the unsaturation of the raw materials, except in instances where special catalysts are used.
Hydrogenolysis has the advantages of cheaper raw materials, wider choice of feed stocks, and wider choice of locations whereas sodium reduction is more flexible (permits production of both saturated and unsaturated fatty alcohols), requires a lower initial investment, involves simpler operation and maintenance, and yields products of superior quality for detergent uses.
The physical and chemical properties of fatty alcohols have been reviewed briefly.
While the largest current market for fatty alcohols lies in the field of detergent preparation, the unsaturated fatty alchols and their derivatives also have many potential uses in the manufacture of such other products as lubricant additives, waxes, and wetting and emulsifying agents. Markets for these fatty alcohols depend upon the results of application research and product development.
Similar content being viewed by others
References
Kraft, F., Ber.,16, 1,714 (1883).
Bouveault, L., and Blanc, G., Compt. rend.,136, 1,676 (1903);ibid., 137, 328 (1903);ibid., Bull. Soc. Chem.,29, 787 (1903);ibid., 31, 666 (1904).
Adkins, H., and Conner, R., J. Am. Chem. Soc.,53, 1,091, 1,095 (1931).
Hansley, V. L., Ind. Eng. Chem.,39, 55 (1947).
Kastens, M. L., and Peddicord, H., ibid. 438 (1949).
Kamlet, J., (Emery Industries Inc.), U. S. Patent 2,563,044 (1951).
Henke, C. O., and Parmelee, H. M. (E. I. DuPont de Nemours and Co.), U. S. Patent 2,104,803 (1953).
Blinka, J., and Peddicord, H. J. (The Procter and Gamble Co.), U. S. Patent 2,647,932.
U. S. Patents: 1,839,974 (1932); 2,009,948 (1935); 2,079,414 (1937); 2,080,419 (1937); 2,094,127 (1937); 2,109,844 (1938); 2,127,367 (1938); 2,114,717 (1938); 2,116,552 (1938); 2,241,417 (1941); 2,340,343 (1944); 2,340,344 (1944); 2,340,687 (1944); 2,340,690 (1944); 2,340,691 (1944); 2,347,562 (1944); 2,375,495 (1945); 2,374,379 (1945); 2,389,284 (1945); 2,413,612 (1946).
British Patents: 569,923 (1945); 570,057 (1945); 582,699 (1946); 589,380 (1947); 585,219 (1947); 584,939 (1947).
French Patent 802,542 (1936).
German Patent 662,731 (1938).
Italian Patents: 430,809; 420,794 (1948).
Sinozaki, Y., and Sumi, S., J. Agr. Chem. Soc., Japan,14, 1,113 (1938);ibid., 15, 531 (1939).
Komori, S., J. Soc. Chem. Ind. Japan,41, 219 (1938);ibid., 43, 34, 122, 337, 428 (1940);ibid., 44, 740 (1941);ibid., 45, 141 (1942).
Sinozaki, Y., and Sumi, S., J. Agr. Chem. Soc., Japan,16, 23 (1940).
Iwai, J. Nippon Oil Technol. Soc.,2, No. 6, 19 (1949).
Komori, S., J. Chem. Soc., Japan, Ind. Chem. Sec.,55, 237 (1952).
Guyer, A.,et al., Helv. Chim. Acta,30, 39 (1947).
U. S. Patent 2,413,612 (1946); British Patents: 582,699 (1946); 584,939; 585,219; 589,380 (1947).
The DeNora High Pressure Hydrogenation Process for the Manufacture of Higher Alcohols, The Lummus Company, 385 Madison avenue, New York 17.
U. S. Patent 1,963,997 (1934).
Knight, H. B., Witnauer, L. P., Coleman, J. S., and Noble, W. R. Jr., Anal. Chem,24, 1331 (1952).
Stage, H., Fette u. Seifen,53, No. 11, 677 (1951).
Doss, M. P., “Properties of the Principal Fats, Fatty Oils, Waxes, Fatty Acids and Their Salts,” The Texas Company, New York (1952).
Descollognes, L., Am. Perfumer Essent. Oil Rev.,23, 237 (1928).
Prins, H. J., ibid. 68 (1917).
Prevost, R. H., Chem. Age (London)37, 269 (1937).
Redgrove, H. S., Am. Perfumer,38, No. 2, 32 (1939).
Stiepel, C., German Patent 476,261 (1925).
Jannaway, S. P., Perfumery Essent. Oil Record,30, 45 (1939).
Sedgwick, F. H., Soap, Perfumery, and Cosmetics,12, 161 (1939).
Elliot, C. J., Australian J. Pharm.,31, 111 (1950).
Gialdi, F., and Nascimbene, A., Farm. sci. e tech.,4, 166 (1949).
Halpern, A., and Zopf, L. C., J. Am. Pharm. Assoc., Sci. Ed.,36, 101 (1947).
Husten, M. J., Riedel, B. E., Murray, J. R., and Groves, G. A., Am. Profess. Pharmacist,15, 145 (1949).
Holliday, C. B., Perfumery Essent. Oil Record,34, 111 (1943).
Doubleday, C., Soap., Perfumery and Cosmetics,28, 715 (1950).
Augustin, J., Mfg. Chemist,6, 77 (1935); Soap,11, No. 5, 59 (1935).
Chem. Age (London),62, 921 (1950).
Stirton, A. J., Weil, J. M., Stawitzke, A. A., and James, S., J. Am. Oil Chemists’ Soc.,29, 198 (1952).
Schoeller, C., and Wittwer, M., (I. G. Farben) U. S. Patent 1, 970,578 (1934).
Sisley, J. P., Industrie chim. belge.,18, 225 (1953).
Gavlin, G., Swire, E. A., and Jones, S. P. Jr., Ind. Eng. Chem.,45, 2,327 (1953); Revukas, A. J., (Tide Water Associated Oil Company) U. S. Patent 2, 489,671 (1949).
Copenhaver, J. W., and Bigelow, M. H., “Acetylene and Carbon Monoxide Chemistry,” p. 55, New York, Reinhold Publishing Corporation, 1949.
Swern, Daniel, Findley, T. W., and Scanlan, T. J., J. Am. Chem. Soc.,66, 1,926 (1944).
Knight, H. B., Koos, R. E., and Swern, D., Ibid. 6,214 (1953).
Arundale, E., and Kodeska, L. A., Chem. Rev.,51, 505 (1952).
Groggins, “Unit Processes in Organic Synthesis,” 4th ed., p. 555, New York, McGraw-Hill Book Company, 1952.
Pryde, E. H., J. Am. Oil Chemists’ Soc.,28, 16 (1951).
Author information
Authors and Affiliations
About this article
Cite this article
Wilson, G.R. Fatty alcohols. J Am Oil Chem Soc 31, 564–568 (1954). https://doi.org/10.1007/BF02638573
Issue Date:
DOI: https://doi.org/10.1007/BF02638573