Fatty acid amides. IV. Reaction of fats with ammonia and amines

Abstract

SummaryConditions 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.

Plant oil-based epoxy resins from fatty diamines and epoxidized vegetable oil

“…The fatty amides typically result from the reaction of fatty acids or triglycerides with ammonia 29 or an amine with an activated fatty acid, such as fatty acyl chloride. 30 Aminated Fatty Diamide AFDA FA produce fatty amides, such as oleoyl-N-methyl-glucamide, 31 and catalyze 32 the coupling between amines and fatty acids.…”

Methods for the preparation of lysophosphatidylcholine

“…Fatty acids (Roe, Scanlan & Swern, 1949) and triglycerides (Roe, Stutman & others, 1952;Naudet, Sambuc & others, 1952) react with ethanolamine to give longchain N-2-hydroxyethylamides (ethanolamides). PC has now been found to react similarly, and under suitable conditions can be converted to PC and ethanolamide; The latter is a non-ionic surfactant and, like LPC, occurs naturally in animal tissues (Bachur, Masek & others, 1965), in bean leaves, wheat and soya beans (Wren & Merryfield, 1965) and in peas (Quarles, Clarke & Dawson, 1968).…”

Instability of an aromatic amine in fatty food and fatty food simulant: characterisation of reaction products and prediction of their toxicity

“…Several authors synthesised fatty acid amides from amines and fatty acids (Swern et al 1949;Roe, Stutzman et al 1952;Roe, Miles et al 1952). Many years after, Cravatt et al (1995) verified that similar compounds belonging to the class of fatty acid amides had pharmacological effects (Cravatt et al 1996).…”