A chemo-enzymatic process for sequential kinetic resolution of (R,S)-2-octanol under microwave irradiation |
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| Institution: | 1. Key Laboratory for Molecular Enzymology and Engineering of Ministry of Education, Jilin University, Changchun 130023, PR China;2. Department of Chemical Technology and Applied Chemistry, College of Chemistry, Jilin University, Changchun 130023, PR China;1. Dipartimento di Ingegneria Chimica Materiali Ambiente, Sapienza Università Di Roma, Via Eudossiana 18, 00184 Roma, Italy;2. ENEA, Italian National Agency for New Technologies, Energy and Sustainable Economic Development, Via Anguillarese 301, 00123 Rome, Italy;1. Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, CA 92697-2025, USA;2. City Hope Comprehensive Cancer Center, Beckman Research Institute, Department of Molecular Medicine, 1500 E. Duarte Road, Duarte, CA 91010, USA;1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, Zhejiang, PR China;2. College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, PR China |
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| Abstract: | A combination of the enzymatic resolution and chemical racemization for the heterogeneous sequential kinetic resolution (SKR) was employed to resolve (R,S)-2-octanol under microwave irradiation. Mesoporous molecular sieves SBA-15, alumina and strong basic styrene anion exchange resin were screened and selected as the optimum supports to immobilize the lipase from Pseudomonas sp. (PSL), oxidant-Chromium trioxide (CrO3) and reductant-Sodium borohydride (NaBH4), respectively. The immobilized catalysts exhibited good reusability: it remained 90%, 72% and 80% of their initial activities after five reuses for the immobilized lipase, the immobilized oxidant and the immobilized reductant, respectively. Further, the E values of the immobilized PSL was increased from 23 under conventional heating to 40 under microwave irradiation in resolution of (R,S)-2-octanol. The immobilized catalysts were then used in SKR of (R,S)-2-octanol under microwave irradiation after optimizing the reaction media. Under the optimum conditions, (R)-2-octanol acetate was obtained at 99% enantiomeric excess with 84% yield in 2 h. |
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