Supercritical Fluid Extraction, a Novel Method for Production of Enantiomers

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Abstract

Extraction of 25 different binary mixtures of racemic acids [2-(4-isobutylphenyl)propionic acid, cis-and trans-chrysanthemic, and -permetric acid] and various chiral bases with supercritical carbon dioxide permitted the conclusion that molecular chiral differentiation in a supercritical fluid is more efficient than in conventional solvents. In the majority of cases, however, complete separation could not be achieved. In five cases, remarkable partial resolutions were realized (30-75% ee) and resolution was possible on a preparative scale. The pair cis-chrysanthemic acid and (S)-(+)-2-(benzylamino)-1-butanol was studied in detail. Pressure, temperature, time, as well as the molar ratio of base and acid had a marked influence on the quantity and quality of the products. Increasing pressure or decreasing temperature resulted in higher ee values. (-)-cis-Chrysanthemic acid in 99% ee was obtained from the raffinate in a single extraction step. Multiple extractions produced the (+)-cis-acid in 90% ee.

Original languageEnglish
Pages (from-to)4390-4394
Number of pages5
JournalJournal of Organic Chemistry
Volume62
Issue number13
DOIs
Publication statusPublished - Jan 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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