Chemoenzymatic dynamic kinetic resolution of rac-1-phenylethanol in ionic liquids and ionic liquids/supercritical carbon dioxide systems.
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.
Lozano
Pedro
P
Departamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Universidad de Murcia, P.O. Box 4021, E-30100 Murcia, Spain.
De Diego
Teresa
T
Larnicol
Mickaël
M
Vaultier
Michel
M
Iborra
José L
JL
D001592:Benzyl Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002245:Carbon Dioxide / Q000737:chemistry*; D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D005656:Fungal Proteins; D052578:Ionic Liquids / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D008956:Models, Chemical; D015394:Molecular Structure; D013237:Stereoisomerism
D001592:Benzyl Alcohols; D005656:Fungal Proteins; D052578:Ionic Liquids; D002245:Carbon Dioxide; C002017:methylphenyl carbinol; D008049:Lipase; C431349:lipase B, Candida antarctica