Enzymatic synthesis of glycamide surfactants by amidification reaction
1997; Elsevier BV; Volume: 53; Issue: 14 Linguagem: Inglês
10.1016/s0040-4020(97)00181-6
ISSN1464-5416
AutoresThierry Maugard, Magali Remaud‐Siméon, Dominique Pétré, Pierre Monsan,
Tópico(s)Hemoglobin structure and function
ResumoThe condensation of a secondary amine (N-methyl-glucamine) with oleic acid was selected as a reaction model to study the production of glycamide surfactants by enzymatic amidification. Reactions catalyzed by immobilized 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 allowing the synthesis of either amide, ester or amide-ester. At 90°C and with a N-methyl-glucamine / acid ratio of 1, a 100% conversion yield 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 various amines and acyl donors. This process is the first that describes successful amide bond synthesis from a hydroxylated secondary amine and fatty acid or fatty acid ester.
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