A hybrid process for chiral separation of compound-forming systems

Chirality. 2011 Feb;23(2):118-27. doi: 10.1002/chir.20886. Epub 2010 Sep 15.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallization
  • Ethers / chemistry*
  • Hydroquinones / chemistry*
  • Mandelic Acids / chemistry*
  • Mandelic Acids / isolation & purification*
  • Membranes, Artificial
  • Models, Chemical
  • Quinidine / chemistry
  • Solubility
  • Stereoisomerism
  • Tetrahydronaphthalenes / chemistry

Substances

  • Ethers
  • Hydroquinones
  • Mandelic Acids
  • Membranes, Artificial
  • Tetrahydronaphthalenes
  • hydroquinine-4-methyl-2-quinolylether
  • Quinidine
  • mandelic acid