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

Biotechnol Lett. 2006 Oct;28(19):1559-65. doi: 10.1007/s10529-006-9130-7. Epub 2006 Aug 10.

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 degrees 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][NTf(2)], [btma][NTf(2)] and [bmim][PF(6)]). 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzyl Alcohols / chemical synthesis*
  • Benzyl Alcohols / chemistry*
  • Carbon Dioxide / chemistry*
  • Chromatography, Supercritical Fluid / methods*
  • Fungal Proteins
  • Ionic Liquids / chemistry*
  • Kinetics
  • Lipase / chemistry*
  • Models, Chemical
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzyl Alcohols
  • Fungal Proteins
  • Ionic Liquids
  • Carbon Dioxide
  • methylphenyl carbinol
  • Lipase
  • lipase B, Candida antarctica