N-Substituted Amides of Natural Fatty Acids

Though the reaction temperature, of course, generally depends on the employed solvent, it is within a temperature range of from—20 ° C. to near the boiling point of the solvent. The reaction is preferably carried on in an atmosphere of such an inactive gas as nitrogen, helium and the like. Thus, the amide derivatives of the objective products are obtained under relatively mild conditions in high yields and simplicity without oxidation of the reactant. 

In case of the direct reaction of the natural oil or lower alkyl ester of natural fatty acid and the amine the reaction method for producing the amide derivatives is as follows That is, about 1 mol of the said oils and 1 to 100 equivalent mols of the said amines are mixed in the absence or presence of solvents such alcohols as methanol, ethanol or the like, such aromatic hydrocarbons as benzene, toluene, xylene or the like, such halogenoalkanes as methylene chloride, chloroform, carbon tetrachloride or the like, and such alkenes or alkanes as petroleum ether, benzene, gasoline, ligroin or cyclohexane, such ethers as tetrahyrofuran, dioxane and the like, or a mixture thereof, and the mixture is subjected to the reaction in the absence or presence of catalyst amount or equimolar amount to the amine of an auxiliary agent of condensation, such as alkoholate of alkali metal, i.e. lithium, methylate, lithium ethylate, sodium methylate, sodium ethylate, potassium-t-butylate and the like, or acidic auxiliary agents, i.e. p-toluenesulfonic acid and the like, thereby to yield the amide derivatives. In this reaction, a formal alcohol may be removed from the reaction system. 

It is a matter of course that even absence of any solvents and any auxiliary agents can sufficiently accomplish the purpose. 

In case of using amines having lower boiling point, if necessary, an autoclave may be employed but in case of another amines the reaction mixture is stirred under atmospheric pressure while being heated at need, thereby easily to yield the objective amide. 

In carrying out the reaction, a mixture of respective substance is stirred at a suitable temperature of between, room temperature and 400° C. for about 3 hours to a month. 

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Seki, T. N-Substituted Amides of Natural Fatty Acids 1970 US 3,551,462 Seki, T. et al N-Substituted Octadecadienoic Acid Amides as Cholesterol Lowering Agents 1971 US 3,621,043... 

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