Engineering Aspects of the Lipase-Catalyzed Production of (R)-1-Ferrocenylethylacetate in Organic Media

Abstract

In this study we investigated aspects of the lipase-catalyzed optical resolution of 1-ferrocenylethanol by esterification. Lipase PS (Amano Pharmaceutical Co.) is the most effective enzyme, toluene the best solvent and vinyl acetate should be used as acylating agent. The water content and the temperature of the reaction system have a significant influence on the enantioselectivity and on the activity of the enzyme. In an attempt to develop a continuous reaction system, different immobilization methods and several carriers have been examined. It was found that adsorption is more favourable than covalent binding. The kinetics of the native and the immobilized enzyme have been determined. Due to strong attrition effects found in a stirred tank reactor, mechanical mixing must be avoided. Fixed bed reactors seem to be suitable for a large scale process. In a fixed bed reactor with recirculation, engineering aspects such as mass transfer have been investigated. On the basis of promising results, a continuous fixed bed reactor has been developed. For a reactor operating at a conversion of 40% and T= 30°C a space-time yield of 1.28 kg (R)-FEA/(1 d) was obtained.