1. A hybrid process for chiral separation of compound-forming systems.
- Author
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Gou L, Robl S, Leonhard K, Lorenz H, Sordo M, Butka A, Kesselheim S, Wolff M, Seidel-Morgenstern A, and Schaber K
- Subjects
- Crystallization, Membranes, Artificial, Models, Chemical, Quinidine chemistry, Solubility, Stereoisomerism, Tetrahydronaphthalenes chemistry, Ethers chemistry, Hydroquinones chemistry, Mandelic Acids chemistry, Mandelic Acids isolation & purification
- 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., (Copyright © 2010 Wiley-Liss, Inc.)
- Published
- 2011
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