BACKGROUND Enzymatic reactive distillation (ERD) is a biocatalyzed process, in which enzymes are immobilized in catalytic packing. The combination of enzymatic reaction and thermal separation helps to overcome chemical reaction and phase equilibrium limitations. Processing of chiral molecules, in particular, can benefit from ERD application, which might lead to more eco‐efficient processing of these valuable chemicals. Therefore an integrated approach to evaluate this technology is followed. RESULTS To evaluate ERD the transesterification of racemic (R/S)‐1‐phenylethanol (RPE/SPE) to (R)‐phenylethyl acetate (PEA) catalyzed by Candida antarctica lipase B (EC: 3.1.1.3) is investigated with regard to kinetics and physical property data, which provide a basis for the modeling of an ERD process. Furthermore, ERD experiments show a selective conversion of RPE to PEA, which is predicted by the established ERD model with high accuracy. CONCLUSION The ERD experiments demonstrate the feasibility of chiral processing for the transesterification by means of ERD and a validated ERD model is developed, allowing for a conceptual evaluation of ERD. This provides the basis for a future comparison of ERD with benchmark processes that will reveal the economic potential of ERD processes. © 2017 Society of Chemical Industry