A hybrid process for chiral separation of compound-forming systems

• Published in: Chirality (New York, N.Y.) Vol. 23; no. 2; pp. 118 - 127
• Main Authors: Gou, Linzhu, Robl, Simone, Leonhard, Kai, Lorenz, Heike, Sordo, Magdalena, Butka, Annamaria, Kesselheim, Stefan, Wolff, Morris, Seidel-Morgenstern, Andreas, Schaber, Karlheinz
• Format: Journal Article
• Language: English
• Published: Hoboken Wiley Subscription Services, Inc., A Wiley Company 01.02.2011
• Subjects: carrier; Carriers; Chirality; COSMO-RS; Crystallization; enantiomers; Enrichment; Ethers - chemistry; Hybrid systems; Hydroquinones - chemistry; liquid membrane; Liquid membranes; mandelic acid; Mandelic Acids - chemistry; Mandelic Acids - isolation & purification; Mathematical models; Membranes, Artificial; Models, Chemical; pertraction; Quinidine - chemistry; Reproduction; Screening; Solubility; Stereoisomerism; Tetrahydronaphthalenes - chemistry
• ISSN: 0899-0042; 1520-636X; 1520-636X
• DOI: 10.1002/chir.20886

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.