화학공학소재연구정보센터
Enzyme and Microbial Technology, Vol.25, No.8-9, 745-752, 1999
Part I. Enzymatic synthesis of lactate and glycolate esters of fatty alcohols
Optimum conditions were determined for the esterification reactions of lactic and glycolic acids with fatty alcohols (C8-C16) in the presence of a lipase from Candida antarctica. This synthetic method gives nearly complete conversion to the desired ester in a relatively short time with high volumetric productivity. In acetonitrile the maximum yields of dodecyl lactate (95% in 48 h) and glycolate (87% in 24 h) were obtained in the presence of a desiccant and 0.28% (w/w) added water, respectively. The procedure permits one to increase substrate concentrations without significant adverse effects on the yield of lactate ester for lactic acid concentrations of 0.25 to 1 M. Similar yields of lactate ester (94-96%) were obtained for alcohol chain lengths from C8 to C16. Although esterification of lactic acid with fatty alcohols is not favored in apolar solvents (e.g. n-hexane), esterification of glycolic acid in n-hexane produces high yields of the glycolate ester (96% in 4 h). In the solvent-free system, esterification of lactic acid with a fatty alcohol requires the presence of desiccant from the beginning of the process (yield of 70% in 48 h). For the reactions of glycolic acid, a strategy in which a desiccant is added after 24 h of reaction gives the maximum yield of the glycolate ester (91%) in a shorter time (48 h of total reaction time). Alternatively, transesterification between the alcohol of interest and ethyl lactate increases the maximum yield of dodecyl lactate (87% in 24 h).