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Chemoenzymatic dynamic kinetic resolution of rac-1-phenylethanol in ionic liquids and ionic liquids/supercritical carbon dioxide systems

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Abstract

Continuous dynamic kinetic resolution processes in different ionic liquid/supercritical carbon dioxide biphasic systems were carried out by simultaneously using both immobilized Candida antarctica lipase B (Novozym 435) and silica modified with benzenosulfonic acid (SCX) catalysts at 40°C and 10 MPa. SCX was seen to act as an efficient heterogeneous chemical catalyst for the racemization of (S)-1-phenylethanol in different ionic liquid media ([emim][NTf2], [btma][NTf2] and [bmim][PF6]). Coating both chemical and enzymatic catalysts with ILs greatly improved the efficiency of the process, providing a good yield (76%) of (R)-1-phenylethyl propionate product with excellent enantioselectivity (ee = 91–98%) in continuous operation.

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Acknowledgements

This work was partially supported by the CICYT CTQ2005-01571/PPQ grant. We thank Ms. C. Saez for her technical assistance and Mr. R. Martínez from Novozymes España, S.A. for the gift of enzymes. M.␣Larnicol is an Erasmus student from the University of Rennes-1. France.

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Authors and Affiliations

  1. Departamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, P.O. Box 4021, E-30100, Murcia, Spain

    Pedro Lozano, Teresa De Diego, Mickaël Larnicol & José L. Iborra

  2. Université de Rennes-1, Institut de Chimie, UMR-CNRS 6510, , Campus de Beaulieu, Av. Général Leclerc, F-35042, Rennes, France

    Michel Vaultier

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  1. Pedro Lozano
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  2. Teresa De Diego
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  3. Mickaël Larnicol
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  4. Michel Vaultier
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  5. José L. Iborra
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Correspondence to José L. Iborra.

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Lozano, P., De Diego, T., Larnicol, M. et al. Chemoenzymatic dynamic kinetic resolution of rac-1-phenylethanol in ionic liquids and ionic liquids/supercritical carbon dioxide systems. Biotechnol Lett 28, 1559–1565 (2006). https://doi.org/10.1007/s10529-006-9130-7

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  • DOI: https://doi.org/10.1007/s10529-006-9130-7

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