Simultaneous kinetic resolution of chiral propylene oxide and propylene glycol in a continuous reactive distillation column

Abstract Traditionally kinetic resolutions are conducted by batch processing to recover one of the desired enantiomers of the racemate, while the product formed by the resolution is discarded due to its low purity. However, chiral materials are economically valuable and simultaneously conducting the reaction and separation, using reactive distillation, allows for both a reactant enantiomer and a product enantiomer to be recovered in high enantiomeric excess and yield. A feasible design of a continuous reactive distillation column is presented which performs a simultaneous kinetic resolution of racemic propylene oxide to produce both enantiomerically-pure propylene oxide and propylene glycol.

[1]  Rajamani Krishna,et al.  Modelling reactive distillation , 2000 .

[2]  Michael F. Doherty,et al.  Design method for kinetically controlled, staged reactive distillation columns , 1998 .

[3]  Stephen Stinson,et al.  CHIRAL DRUG MARKET SHOWS SIGNS OF MATURITY , 1997 .

[4]  Eric N. Jacobsen,et al.  Polymer-Supported Chiral Co(Salen) Complexes: Synthetic Applications and Mechanistic Investigations in the Hydrolytic Kinetic Resolution of Terminal Epoxides , 1999 .

[5]  M. Doherty,et al.  Vapor-liquid phase equilibrium in systems with multiple chemical reactions , 1995 .

[6]  M. Tokunaga,et al.  Asymmetric catalysis with water: efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis. , 1997, Science.

[7]  G. Mestroni,et al.  Asymmetric hydrogen transfer reactions from propan-2-ol to ketones catalyzed by Ir(I) derivatives with chiral Schiff bases , 1987 .

[8]  Stephen Stinson,et al.  CUSTOM CHEMICALS: Relationships between companies that produce chemicals to special order and their clients become closer, as some 'virtual' firms contract out most activities , 1997 .

[9]  R. Sheldon.  Chirotechnology: Industrial Synthesis of Optically Active Compounds , 1993 .

[10]  James M. Douglas,et al.  Conceptual Design of Chemical Processes , 1988 .

[11]  Stephen Stinson.  DELVING INTO DENDRIMERS , 1997 .

[12]  Stephen Stinson,et al.  PROTECTING GROUPS : NEW WAYS ON AND OFF , 1997 .

[13]  Shih-Hsiung Wu,et al.  Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems , 1987 .

[14]  John J. McKetta,et al.  Encyclopedia of Chemical Processing and Design , 1976 .