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A hybrid process for chiral separation of compound‐forming systems
Authors:Linzhu Gou  Simone Robl  Kai Leonhard  Heike Lorenz  Magdalena Sordo  Annamaria Butka  Stefan Kesselheim  Morris Wolff  Andreas Seidel‐Morgenstern  Karlheinz Schaber
Affiliation:1. Max Planck Institute for Dynamics of Complex Technical Systems, Physical and Chemical Foundations of Process Engineering, D‐39106 Magdeburg, Germany;2. Karlsruhe Institute for Technology (KIT), Institute for Technical Thermodynamics and Refrigeration (ITTK),76131 Karlsruhe, Germany;3. RWTH Aachen, Chair for Technical Thermodynamics, 52062 Aachen, Germany;4. Engineering Thermodynamics, Process & Energy Department, 2628 CA Delft, Netherlands;5. Otto‐von‐Guericke‐University, Department of Chemical Engineering, D‐39106 Magdeburg, Germany
Abstract:
The resolution of chiral compound‐forming systems using hybrid processes was discussed recently. The concept is of large relevance as these systems form the majority of chiral substances. In this study, a novel hybrid process is presented, which combines pertraction and subsequent preferential crystallization and is applicable for the resolution of such systems. A supported liquid membrane applied in a pertraction process provides enantiomeric enrichment. This membrane contains a solution of a chiral compound acting as a selective carrier for one of the enantiomers. Screening of a large number of liquid membranes and potential carriers using the conductor‐like screening model for realistic solvation method led to the identification of several promising carriers, which were tested experimentally in several pertraction runs aiming to yield enriched (+)‐(S)‐mandelic acid (MA) solutions from racemic feed solutions. The most promising system consisted of tetrahydronaphthalene as liquid membrane and hydroquinine‐4‐methyl‐2‐quinolylether (HMQ) as chiral carrier achieving enantiomeric excesses of 15% in average. The successful production of (+)‐(S)‐MA with a purity above 96% from enriched solutions by subsequent preferential crystallization proved the applicability of the hybrid process. Chirality, 2011. © 2010 Wiley‐Liss, Inc.
Keywords:enantiomers  liquid membrane  pertraction  carrier  COSMO‐RS  crystallization  solubility  mandelic acid
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