Ultrasound-assisted enzymatic synthesis of xylitol fatty acid esters in solvent-free conditions

Abstract

A commercial immobilized lipase was successfully used for the synthesis of five xylityl acyl esters by means of the esterification of free fatty acids (caprylic, capric, lauric and myristic, respectively) with xylitol under solvent-free conditions. Ultrasound-assistance was shown to be a key tool to overcome the handicap imposed by both the mutual immiscibility of fatty acids and xylitol substrates, and the semisolid character of the initial reaction mixtures. In such semisolid systems, ultrasonic irradiation may enable the transport of substrate molecules to the enzyme catalytic-site, leading to the efficient synthesis of xylityl fatty ester (e.g. up to 95% yield after 90 min at 40ºC), with xylityl monoacyl ester and xylitol diacyl ester appearing as the main products (>96%), assessed by HPLC and NMR analyses. The separation of products was carried out by heating and simple centrifugation of the reaction medium, which was possible due to different densities of the resulting fractions.