ENZYMATIC-SYNTHESIS OF GLYCAMIDE SURFACTANTS BY AMIDIFICATION REACTION

The condensation of a secondary amine (N-methyl-glucamine) with oleic acid was selected as a reaction model to study the production of glyca mide surfactants by enzymatic amidification. Reactions catalyzed by im mobilized lipase from Candida antarctica were carried out in 2-methyl- 2-butanol. The acido-basic conditions (through the N-methyl-glucamine/ oleic acid ratio) control the chemoselectivity of the reaction allowin g the synthesis of either amide, ester or amide-ester. At 90 degrees C and with a N-methyl-glucamine/acid ratio of 1, a 100% conversion yiel d with 97% of amide synthesis was obtained in less than 50 hours. The process was applied to the preparation of a range of amides using vari ous amines and acyl donors. This process is the first that describes s uccessful amide bond synthesis from a hydroxylated secondary amine and fatty acid or fatty acid ester. (C) 1997 Elsevier Science Ltd.