Scale-up of pseudo solid-phase enzymatic synthesis of α-methyl glucoside acrylate

Abstract

The successful scale-up of the enzymatic synthesis of α-methyl glucoside acrylate from laboratory scale (milliliter) to pilot-scale (liter) was examined. Specifically, Candida antarctica lipase B (Novozym 435) was used as a biocatalyst to produce α-methyl glucoside acrylate via the transesterification of α-methyl glucoside (MG) with vinyl acrylate (VA) using acetone as a solvent. This is a pseudo-solid-phase synthesis; only a fraction of the α-methyl glucoside and the product are soluble in acetone. Molecular sieves were used to remove traces of water in the reaction medium and to increase enzyme stability by removing the acetaldehyde by-product. A general method was also developed to purify and recover the monoacrylate product from unreacted sugar and undesired diester by a simple crystallization and precipitation process. © 2002 Wiley Periodicals, Inc.