Resolution of racemic trans-2-methyl-1-cyclohexanol by lipase-catalysed transesterification in a membrane reactor

A kinetic resolution of trans-2-methyl-1-cyclohexanol with transesterification was studied using a membrane reactor. The highest enantioselectivity was observed for the reaction with vinyl acetate in an n-hexane solution, which was catalysed by lipase from Pseudomonas sp. It was also found that the use of both native lipase and that immobilised in a polyamide hollow-fibre membrane leads to conversion of the (1R;2R)-enantiomer. However, the catalytic activity of the immobilised lipase was equal to 27% of that of the native one. Operating conditions for the membrane reactor, such as the kind of solvent, amount of water, temperature, and concentrations of substrates, were examined and optimised. Under the optimum conditions, the kinetics of the process are characterised by the constants of the Michaelis–Menten equation, KM and Vmax, being as high as 1.702×10−2 M and 3.903×10−4 mol/h mg, respectively.