Lipase Catalysis in Ionic Liquids and Supercritical Carbon Dioxide at 150 °C

Abstract

Free and immobilized Candida antarctica lipase B dispersed in ionic liquids (1-ethyl-3-methylimidazolium bistriflimide and 1-buthyl-3-methylimidazolium bistriflimide) were used as catalyst for the continuous kinetic resolution of rac-1-phenylethanol in supercritical carbon dioxide at 120 and 150 degrees C and 10 MPa. Excellent activity, stability and enantioselectivity levels were recorded in continuous operation.

Immobilization of Proteins in Poly-Styrene-Divinylbenzene Matrices: Functional Properties and Applications

“…These systems were employed as biocatalyst for the kinetic resolution of rac-1-phenylethanol in supercritical CO 2 at 150°C and 10 MPa under a continuous regime. The enzyme showed excellent activity, stability and enantioselectivity under continuous operation [76].…”

“…One pioneer example of the use of ionic liquids combined with supercritical fluids was demonstrated for the lipase B from C. antarctica [76]. The free and immobilized forms of the lipase were dispersed in different ionic liquids (1-ethyl-3-methylimidazolium bistriflimide and 1-butyl-3-methylimidazolium bistriflimide).…”

Application of Ionic Liquids in Biocatalysis

“…The protective effect of ILs towards enzyme deactivation by temperature or CO 2 was demonstrated by the observed increase in synthetic activity of the enzyme when it was assayed in the presence of IL. Studies based on enzymatic kinetic resolution of rac-1-phenylethanol with vinyl propionate performed in SC CO 2 /ILs biphasic systems have been reported (Lozano et al, 2006;Lozano et al, 2003). Both free and immobilized CALB were able to catalyze specifically the synthesis of (R)-1-phenylethyl propionate in SC CO 2 /ILs biphasic systems, and excellent activity, stability and enantioselectivity levels were recorded.…”

“…Both free and immobilized CALB were able to catalyze specifically the synthesis of (R)-1-phenylethyl propionate in SC CO 2 /ILs biphasic systems, and excellent activity, stability and enantioselectivity levels were recorded. The suitability of CALB to catalyze the stereoselective transesterification of (R)-1-phenylethanol from the racemic mixture has been widely demonstrated (Lozano et al, 2004;Lozano et al, 2003;Eckstein et al, 2002;Suan & Sarmidi, 2004). When continuous dynamic kinetic resolution (DKR) was performed in SC CO 2 /IL biphasic media with simultaneous presence of immobilized CALB the improvement of DKR process was observed.…”

“…Since most of the organic compounds are soluble in SC CO 2 , with the high solubility of SC CO 2 in ILs, these products are transferred from the IL to the supercritical phase ). Recent researches have demonstrated the possibility to carry out integral green biocatalytic processes by combining SC CO 2 and ILs with enzymes (Lozano et al, 2003;Lozano et al, 2004;Lozano et al, 2007a;Miyawaki & Tatsuno, 2008;Knez, 2009;Fan & Qian, 2010), because their different miscibilities produce the two-phase systems that show an exceptional ability to carry out both the biotransformation and the products extraction steps simultaneously. In our studies, ILs were used as reaction media for lipase-catalyzed kinetic resolution of (R,S)-1-phenylethanol with vinyl acetate.…”