Summary
Conditions have been worked out for the quantitative conversion of oleo oil, olive oil, castor oil, and tobacco seed oil to amides and glycerol by reaction with liquid ammonia under pressure. Similarly methyl oleate has been converted to oleamide in excellent yield. The reaction of aqueous ammonia with methyl oleate, however, gives a maximum yield of isolated oleamide of only 50%, apparently because of competition between hydrolytic and ammonolytic reactions.
N-(2-hydroxyethyl)- and N-(n-dodecyl) amides have also been prepared by the reaction of oleo oil with monoethanolamine andn-dodecylamine, respectively, at atmospheric pressure. Particularly significant is the quantitative conversion of oleo oil to N-(2-hydroxyethyl) amides by refluxing with monoethanolamine for only 15 minutes. The conversion to N-(n-dodecyl) amides however required three hours heating at 230° C. withn-dodecylamine, and conversion to unsubstituted amides required six hours heating at 170°C. under pressure with liquid ammonia.
Crystallization of the amides obtained from the various fats yielded oleamide (purity, 92%) from olive oil, ricinoleamide (purity, >95%) from castor oil, and N-(2-hydroxyethyl) oleamide (purity, 90%) from oleo oil. Little fractionation was accomplished with the amides of tobacco seed oil however. In the fractionation of the unsubstituted and N-(n-dodecyl) amides from oleo oil, fractions which were predominantly saturated and monounsaturated were obtained readily, but no greater purification could be effected by recrystallization.
Unsubstituted and N-(2-hydroxyethyl) amides were readily converted to the corresponding free acids by refluxing for two hours with constant boiling (approximately 20%) aqueous hydrochloric acid.
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The previous paper in this series is reference 14.
One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.
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Roe, E.T., Stutzman, J.M., Scanlan, J.T. et al. Fatty acid amides. IV. Reaction of fats with ammonia and amines. J Am Oil Chem Soc 29, 18–22 (1952). https://doi.org/10.1007/BF02640174
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DOI: https://doi.org/10.1007/BF02640174