Lipase-Catalyzed Transesterification of (R,S)-1-Phenylethanol in SC CO2 and in SC CO2/Ionic Liquid Systems

Muzafera Paljevac, Željko Knez and Maja Habulin*

University of Maribor, Faculty of Chemistry and Chemical Engineering,
Laboratory for separation processes and product design, Smetanova 17, SI-2000 Maribor, Slovenia
* Corresponding author: E-mail:;
Tel.: +38622294462, Fax.: +38622527774

Commercial immobilized lipase B from Candida antarctica (CALB) was successfully applied to catalyzing the transesterification of (R,S)-1-phenylethanol in supercritical carbon dioxide and in supercritical carbon dioxide/ionic liquid biphasic system. Firstly, the variables affecting the performance of CALB in transesterification reactions in supercritical carbon dioxide, such as CALB concentration, temperature and pressure, were studied. An increase in the conversion and in the reaction rate was observed as the CALB/substrate ratio, temperature and pressure, were increased from 4.3 to 19.9, from 40 °C to 80 °C and from 8 MPa to 10 MPa, respectively. Further increase in temperature from 80 °C to 120 °C and pressure from 10 MPa to 30 MPa resulted in lower conversion and lower initial reaction rate. Furthermore, different vinyl esters were used as acyl donors for CALB-catalyzed transesterification of (R,S)-1-phenylethanol in supercritical carbon dioxide. The highest initial reaction rate was attained with vinyl butyrate, although 50% conversion was attained faster when vinyl acetate was used as acyl donor. Secondly, in transesterification of (R,S)-1-phenylethanol, performed in supercritical carbon dioxide/ionic liquid biphasic system, influence of concentration of 1-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4] was studied. The addition of 50 mmol (70% w/w reaction mixture) of [bmim][BF4] to the reaction system gave the best result in terms of transesterification rate.

Keywords: Candida antarctica lipase B, transesterification, (R,S)-1-phenylethanol, vinyl acetate, supercritical carbon dioxide, ionic liquids