Effect of co-solvents in the enantioselective esterification of (R/S)-ibuprofen with ethanol

Abstract

The commercial biocatalyst Novozym 435 was used for the kinetic resolution of (R/S)-ibuprofen by esterification with short chain alcohols (ethanol, 1-propanol and 2-propanol) in the absence of organic co-solvent. The best performance enzymatic was obtained by employing ethanol as reagent and solvent. Due to deleterious effect of this alcohol on the integrity of commercial biocatalyst previously reported are used different organic co-solvents (isooctane, n-hexane, carbon tetrachloride, ethyl acetate, acetonitrile and tetrahydrofuran) that allowed to reduce the volume of ethanol to be used. Thus, was evaluated the effect of the chemical nature of the co-solvent on enantioselective esterification of (R/S)-ibuprofen with ethanol. The results show that the best performance was obtained with the reaction system without co-solvent added, importantly for their sustainability and eco-compatibility. Also demonstrated the need to take into account multiple physic-chemical properties of the solvents to analyze their effects on biocatalysis.