In this work we investigated the feasibility of resolution and production of chiral compounds in an enzymatic reactive distillation column. Here, the transesterification of racemic 1-phenylethanol with isopropenyl acetate was chosen as the model system. Enzyme kinetics with the enzymatic catalyst Candida antarctica lipase B immobilized on polymer beads were investigated experimentally. Based on those, a detailed model of enzymatic reactive distillation was developed and a subsequent model-based process analysis showed the achievement of high conversion rates and a full separation of the reaction products.