Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium

• Published in: Process biochemistry (1991) Vol. 47; no. 3; pp. 496 - 502
• Main Authors: Yadav, Ganapati D., Devendran, Saravanan
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.03.2012
• Subjects: Acetates; Alcohols; carboxylic ester hydrolases; Catalysts; catalytic activity; Cinnamyl acetate; Cosmetics; flavor; industry; ingredients; Lipase; Novozym 435; odors; Organic media; reaction kinetics; regression analysis; solvents; Synthesis; Ternary complex mechanism; toluene; Transesterification; Vinyl acetate; Ternary complex mechanism; Transesterification; Novozym 435; Organic media; Cinnamyl acetate
• ISSN: 1359-5113; 1873-3298
• DOI: 10.1016/j.procbio.2011.12.008

► Lipase catalyzed cinnamyl acetate synthesis from cinnamyl alcohol and vinyl acetate. ► Candida Antarctica B supported polyacrylic resin (Novozym 435) is the best. ► With 1:2mol ratio of alcohol to acetate at 40°C, conversion of 96% in 1h is obtained. ► Cinnamyl alcohol deactivates the enzyme at high concentration. ► Reaction follows the ternary complex mechanism. Cinnamyl acetate is used as flavor and fragrance ingredient in food and cosmetic industries. This work focuses on the synthesis of cinnamyl acetate via lipase catalyzed transesterification of cinnamyl alcohol with vinyl acetate in non-aqueous medium. Among the different immobilized lipases employed, Novozym 435 was found to be the best catalyst in toluene as solvent. The effects of various parameters were studied systematically. With a mole ratio of 1:2 of cinnamyl alcohol to vinyl acetate and 10mg catalyst, 96% conversion was obtained in 1h at 40°C. The ternary complex mechanism with inhibition by cinnamyl alcohol was found to fit the data well. The kinetics of the reaction was studied by using non-linear regression analysis. Enzymatic synthesis of cinnamyl acetate is an efficient process vis-à-vis chemical catalysis.