Chiral resolution of racemic ibuprofen ester in an enzymatic membrane reactor

Abstract

In the present study, the production of ( S)-ibuprofen acid is reported using lipase-catalyzed hydrolysis reaction in a hollow fiber membrane reactor, as an efficient and cleaner route to obtain single-enantiomer compound. The performance of an enzymatic membrane reactor (EMR) was evaluated by varying operating temperature, organic phase flow rate, aqueous phase flow rate and enzyme loadings. The optimal operating conditions: temperature of 40 °C, pH 8 at EMR residence time ( τ org) of 10.87 h (organic inlet flow rate of 80 mL/min) with enzyme loading of 1.78 g/m 2 on the spongy layer of membrane were obtained. The kinetic resolution yielded an E value of 13, 31% ee S and 85% ee P. Both substrate and product purity were achieved by recovering the less reactive substrate in the organic stream while enhancing the optical purity of the desired product in the aqueous stream. The EMR system was modeled by incorporating Michaelis–Menten kinetics and treating the system as a continuous flow stirred tank reactor (CSTR). The simulated results agreed well with the experimental data.