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 o C. 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.

Novel Synthesis and Characterization of Vegetable Oil Derived Corrosion Inhibitors

“…Methylamine was added to react with the oil following the same steps. The products formed in both reactions were (1) [oil+ NH 4 Cl product] and (2) [oil + CH 3 NH 2 ] with same solubility properties [22].…”

Novel Route to Erucamide: Highly Selective Synthesis from Acetonitrile at Room Temperature via a Photo-Fenton Process

“…Fatty acid N-derivatives, i.e., fatty acid nitriles and fatty acid amides, are considerably important molecules in the areas of chemistry − as well as biochemistry. − These molecules are present within living cells − and bear renowned applications in industry ,,− ,− in addition to therapeutics. ,,− The reported synthetic strategies include pyrolysis of biodegradable organic matter ,,− and ammoniolysis of fatty acid precursors, ,− involving extremely high temperatures up to 700 °C. However, there is a sole example that has reported the use of low temperature instead (50 °C using fatty ester) . In the current work, an innovative method to selectively synthesize a fatty acid N-derivative (erucamide) has been reported at room temperature.…”

“…However, there is a sole example that has reported the use of low temperature instead (50 °C using fatty ester). 44 In the current work, an innovative method to selectively synthesize a fatty acid N-derivative (erucamide) has been reported at room temperature. The methodology illustrates the formation of higher homologues from a lower nitrile (MeCN) by means of C−CN activation followed by C− H activation initiated by peroxy free radicals.…”