Solvent-free enzymatic synthesis of fatty alkanolamides.
An environmentally benign and volume efficient process for enzymatic production of alkanolamides is described. Immobilized Candida antarctica lipase B, Novozym435, was used to catalyze the condensation of lauric acid with monoethanolamine. The reaction temperature of 90 degrees C was required to keep the reactants in a liquid state. Stepwise addition of the amine minimized problems caused by the formation of a highly viscous amine/fatty acid ion-pair. The enzyme was both very active and stable under the reaction conditions, with about half of the activity remaining after 2 weeks. The maximum amide yield obtained when using equimolar amounts of the reactants was 75%, which could be increased to 95% upon water removal. Special precautions to avoid co-distillation of the amine were required. Two different strategies to avoid the amine loss are presented.
Tufvesson
Pär
P
Department of Biotechnology, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.
Annerling
Annika
A
Hatti-Kaul
Rajni
R
Adlercreutz
Dietlind
D
D000577:Amides / Q000138:chemical synthesis*; D002175:Candida / Q000201:enzymology; D004983:Ethanolamines / Q000138:chemical synthesis* / Q000737:chemistry*; D005227:Fatty Acids / Q000138:chemical synthesis*; D005656:Fungal Proteins; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D012997:Solvents; D013501:Surface-Active Agents / Q000138:chemical synthesis*
D000577:Amides; D004983:Ethanolamines; D005227:Fatty Acids; D005656:Fungal Proteins; D012997:Solvents; D013501:Surface-Active Agents; D008049:Lipase; C431349:lipase B, Candida antarctica