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RECENTinterest in Z-sorbose arises from its use in the chemical synthesis of vitamin C (Z-ascorbic acid), since it is the configuratively correct starting material for the preparation of this important substance. The successful commercial production of d-sorbitol from glucose in the past few years has provided a ready source of this essential intermediate, but the biological conversion of d-sorbitol to Z-sorbose, the only practical method available, has been somewhat difficult to accomplish. This difficulty is chiefly due to inherent disadvantages of the surface type of fermentation process which has been used in all previous studies on this problem.

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.

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