Abstract
The hydrogenated samples were analyzed by ultraviolet specconditions produced mostly nonselective hydrogenation. The variables of catalyst, catalyst concentration, solvent, temperature, and pressure have very little effect on the selectivity. Large differences were found in the relative reactivities of the three double bonds in methyl linoleate. It appears that the initial reaction strongly favors the 12 position assuming a limited amount of shifting of double bonds during hydrogenation. The solvent has an appreciable effect on this selectivity, but the other variables have only minor effects.
The hydrogenated samples were analyzed by ultraviolet spectroscopy. Efforts to identify the location of the double bonds by oxidative methods were unsatisfactory. Preliminary studies on the possible use of nuclear spin resonance as analytical method in fatty acid analysis look promising.
Similar content being viewed by others
References
Bailey, A.E., J. Am Oil Chemists’ Soc.,26, 644–648 (1949).
Bailey, A.E., and Fisher, G. S., Oil and Soap.,23, 14–18 (1946).
Bauer, and Ermann, Chem. Umschau,37, 241 (1930).
Beadle, B. W., Oil and Soap.,23, 140–145 (1946).
Begemann, P.H., Keppler, J.G., and Boekenoogen, H.A., Rec. Trav. Chim.,69, 439–456 (1950).
Boelhouwer, C., Gerckens, J., Lie, Ong Tian, and Waterman, H.I., J. Am. Oil Chemists’ Soc.,30, 59–61 (1953).
Feuge, R.O., Cousins, E.R., Fore, S.P., Du Pre, E.F., and O’Connor, R.T., J. Am. Oil Chemists’ Soc.,30, 454–460 (1953).
Frampton, V.L., Edwards, J.D., and Henze, H.R., J. Am. Chem. Soc.,73, 4432–4434 (1951).
Hilditch, and Vidyarthi, Proc. Roy. Soc. (London),122A, 563 (1929).
Jones, E.P., and Stolp, J.A., J. Am. Oil Chemists’ Soc.,35, 71–76 (1958).
Lemieux, R.U. and von Rudloff, E., Can. J. Chem.,33, 1701–1709 (1955).
Lemon, H.W., Can. J. Res.,22F, 191 (1944).
Lemon, H.W., Can. J. Res.,25F, 34 (1947).
Lindlar, vonH., Helv. Chim. Acta.,35, 446–450 (1952).
McCutchan, J.W., Org. Syntheses, Collective Vol.3, 531 (1955).
Mitchell, J.H. Jr., Kraybill, H.R., and Zscheile, F.P., Ind. Eng. Chem.,15, 1–3 (1953).
Official and Tentative Methods of the American Oil Chemists’ Society, Tentative Method Cd 7-48.
Rebello, D., and Daubert, B.F., J. Am. Oil Chemists’ Soc.,28, 177–182 (1951).
Rebello, D., and Daubert, B.F., J. Am. Oil Chemists’ Soc.,28, 183–185 (1951).
van der Veen, H., Chem. Umschau, Felte, Oels, Wachse und Harzze,88, 89 (1931).
Author information
Authors and Affiliations
Additional information
A report of work done under contract to the United States Department of Agriculture, authorized by the Research and Marketing Act. The contract was supervised by the Northern Utilization Research and Development Division.
About this article
Cite this article
Willard, J.G., Martinez, M.L. The selective hydrogenation of linolenic acid. J Am Oil Chem Soc 38, 282–286 (1961). https://doi.org/10.1007/BF02638427
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02638427