Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen

Abstract

Supported ionic liquid phase (SILP) was used as a carrier for lipase from Aspergillus oryzae (LAO) and used as a biocatalyst for enantiomeric resolution of racemic ibuprofen via esterification leading to (S) -(+)-ibuprofen ester. Using native form of lipase, outstanding results were achieved, obtaining (S) -(+)-ibuprofen propyl ester with enantiomeric excess ( ee ) of 99.9% and high conversion of racemic ibuprofen after 24 h ( α = 34 . 8 % ) and respectively ee = 99.9% with α = 45 . 2 % after 48 h. Several hybrid materials composited with silica and metal-based oxides including magnesium, calcium, and zirconia were evaluated as supports for LAO with various surface characteristics. The selected ionic liquid 1-methyl-3-(triethoxysilylpropyl)imidazolium bis(trifluoromethylsulfonyl)imide was immobilized via the covalent bound onto the surface of solid material and in the second step LAO was anchored. Optimized results in enantiomeric resolution of racemic ibuprofen (35.23% conversion of rac -ibuprofen after 7 days with 95% ee of ester) were obtained for SILP biocatalyst based on MgO ⋅ SiO 2 (1:1) (ionic liquid loading 6.79%, enzyme loading 3.96%). This is proposed as a generic approach to tailoring supported ionic liquids phase biocatalysts for industrially-relevant reactions, to generate both environmentally and economically sustainable processes. • Aspergillus oryzae lipase was used in enantiomeric resolution of racemic ibuprofen. • Free enzyme showed over 45% reaction yield and 99.9% enantiomeric excess after 48 h. • Supported ionic liquid phase with lipase was used to improve system feasibility. • Modification of surface with ionic liquid enabled efficient immobilization of enzyme. • High reaction rate and enantioselectivity were maintained in the reusability test.