Abstract
Monomeric fatty acids derived from the alkali treatment of linseed oil at temperatures above 200C contain cyclic (1,2-disubstituted cyclohexadiene) and straight-chain fatty acids. Hydrogenation converts cyclic to liquid, saturated cyclic acids that can be recovered in a pure state by crystallization. During hydrogenation (palladium catalyst) some of the unsaturated cyclic acids form aromatic fatty acids by loss of hydrogen and under some conditions are not subsequently hydrogenated. It was necessary to establish conditions for complete hydrogenation since color and oxidative stability at high temperature are inversely related to aromatic content. Previously, the preparation of cyclic acids free of aromatic acids was by hydrogenation in the presence of a high concentration of acetic acid. A further study of reaction variables established conditions to make saturated cyclic fatty acids free of aromatic without acetic acid. Factors favoring the elimination of aromatic acids include a high catalyst concentration, high temperature and pressure, good hydrogen dispersion in the liquid and good agitation.
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References
Beal, R. E. (Secretary of Agriculture), U. S. 3,005,840 (1961).
Black, L. T., and R. A. Eisenhauer, JAOCS40, 272–274 (1963).
DeJarlais, W. J., and H. M. Teeter, Ibid.39, 421–424 (1962).
Eisenhauer, R. A., R. E. Beal and E. L. Griffin, Ibid.40, 129–131 (1963).
Eisenhauer, R. A., R. E. Beal and E. L. Griffin, Ibid.41, 60–63 (1964).
Friedrich, J. P., Anal. Chem.33, 974 (1961).
Friedrich, J. P., and R. E. Beal, Ibid.39, 528–533 (1962).
Friedrich, J. P., E. W. Bell and R. E. Beal, Ibid.89, 9 (1962).
Friedrich, J. P., E. W. Bell and L. E. Gast, Abstr. papers, AOCS 54th Annual Meeting, Atlanta, Ga., 1963, Abstr. C-2.
Friedrich, J. P., J. C. Palmer, E. W. Bell and J. C. Cowan, JAOCS40, 584–587 (1963).
Friedrich, J. P., H. M. Teeter, J. C. Cowan and G. E. McManis, Ibid.38, 329 (1961).
Miller, W. R., H. M. Teeter, A. W. Schwab and J. C. Cowan, Ibid.39, 173–176 (1962).
Scholfield, C. R., and J. C. Cowan, Ibid.36, 631 (1959).
Scholfield, C. R., J. C. Cowan and J. P. Friedrich (Secretary of Agriculture), U. S. 3,041,360 (1962).
Scholfield, C. R., J. C. Cowan and J. P. Friedrich (Secretary of Agriculture), U. S. 3,119,850 (1964).
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No. Utiliz. Res. Dev. Div., ARS, USDA.
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Eisenhauer, R.A., Beal, R.E., Black, L.T. et al. Cyclic fatty acids: Removal of aromatic acids formed during hydrogenation. J Am Oil Chem Soc 43, 515–518 (1966). https://doi.org/10.1007/BF02641279
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DOI: https://doi.org/10.1007/BF02641279