A Novel Synthetic Route to Fatty Amides in Non-aqueous Reaction of Fatty Esters with Ammonium Salts and Methyl Amine

Abstract

Fatty amides have been widely produced by the reaction of ammonia and amines with fatty acids. Fatty amide formation from fatty esters (i.e. the ester-ammonia route) is not widely applied because it does not have much practical value. There are no reported cases of these fatty esters being used directly in amide production. When, however, a fatty ester is to be employed in the production of an amide, the ester is first stripped to the fatty acid. The methods of synthesis employing even the simple esters require in most cases harsh reaction conditions. In this work, a fatty ester (groundnut oil) was hydrolyzed using sodium hydroxide in acetone and reacted in-situ with ammonium chloride and methyl amine at 50 oC. Conversions of more than 80% were obtained in a reaction time of 60 minutes beyond which the reaction attained equilibrium with reversal to starting material. IR, GC/MS and GC-FID analyses of the product samples revealed the presence of amides, ammonium salts, simple as well as mixed anhydrides of fatty acids.