Supported ionic liquid phase facilitated catalysis with lipase from Aspergillus oryzae for enhance enantiomeric resolution of racemic ibuprofen
Creators
- 1. Department of Chemical Organic Technology and Petrochemistry, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, Poland
- 2. Institute of Chemical Technology and Engineering, Faculty of Chemical Technology, Poznan University of Technology, Berdychowo 4, PL-60965 Poznan, Poland
- 3. Institute for Engineering of Polymer Materials and Dyes, Lukasiewicz Research Network, Sklodowskiej-Curie 55, PL-87100 Torun, Poland
Description
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⋅ SiO2 (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.
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Additional details
Funding
- National Science Centre
- Projektowalne ciekłe związki kompleksowe metali jako katalizatory modelowych procesów chemicznych i elektrochemicznych UMO-2020/39/B/ST8/00693