Pseudomonas cepacia lipase catalyzed esterification and transesterification of 3-(furan-2-yl) propanoic acid/ethyl ester: A comparison in ionic liquids vs hexane

A comparison of the Pseudomonas cepacia lipase (lipase PS) catalyzed esterification of 3-(furan-2-yl) propanoic acid and transesterification of ethyl 3-(furan-2-yl) propanoate with six straight chain alcohols (propanol to octanol) in ionic liquids and hexane was carried out. The ionic liquids selected, [Bmim]BF4, [Bmim]PF6, and [Bmim]Tf2N, consisted of an identical cation and different anions. This is the first report on the biocatalyzed synthesis of these esters. In all the media, lipase PS catalyzed esterification of 3-(furan-2-yl) propanoic acid resulted in high yields of the esters compared to the transesterification of ethyl 3-(furan-2-yl) propanoate. [Bmim]Tf2N proved to be the best; yielding 98–67% of the product by lipase PS catalyzed esterification. The lipase PS–[Bmim]Tf2N and lipase PS–[Bmim]PF6 mixture was recycled five times without any decrease in the yields of the products and was found to be operationally stable up to 10 months at room temperature.