Production of l-menthyl acetate through kinetic resolution by Candida cylindracea lipase: effects of alkaloids as additives
(2018) Research on Chemical Intermediates : an international journal — Vol. 44, n° 11, p. 6847-6860 (2018)
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- Authors
Merabet-Khelassi, Mounia 
Aribi-Zouioueche, Louisa
- Abstract
- Enzymatic transesterification of dl-menthol with vinyl acetate in tert-Butyl methyl ether (TBME) catalyzed by Candida cylindracea lipase (CCL) was carried out in the presence of cinchona alkaloid as additive. The effects of various reaction parameters, such as lipase nature and loading, acylating agent, molecular sieves, solvents and various additives, on the reactivity as well as on the enantioselectivity were investigated. A significant improvement of CCL reactivity has been recorded after using cinchona alkaloid as additive in TBME. A high enantiomeric ratio (E = 80) was achieved when 30 mol% of quinidine was added, and l-(-)-menthyl acetate was obtained with 93% optical purity and 49% conversion. This process was easily applied to gram-scale quantities, using commercially inexpensive lipase, providing high yield optically active menthol under mild experimental conditions.
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Citations
Belkacemi, F. Z., Merabet-Khelassi, M., Aribi-Zouioueche, L., & Riant, O. (2018). Production of l-menthyl acetate through kinetic resolution by Candida cylindracea lipase: effects of alkaloids as additives. Research on Chemical Intermediates : an international journal, 44(11), 6847-6860. https://doi.org/10.1007/s11164-018-3525-7 (Original work published 2018)