Application of supercritical fluid extraction for fractionation of enantiomers

Edit Székely, B. Simándi, Rita Illés, Péter Molnár, István Gebefügi, Ildikó Kmecz, E. Fogassy

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

A novel, organic solvent free procedure was developed for separation of enantiomers of a racemate. Partial diastereomeric complex formation of trans-2-chloro-cyclohexan-1-ol and O,O′-dibenzoyl-(2R,3R)-tartaric acid monohydrate was performed in the melt of the alcohol. The highest resolution effiency was achieved, when the unreacted alcohol (R,R-enantiomer, e.e.=43.5%, yield=45.3%) was extracted with supercritical carbon dioxide at mild conditions (100 bar, 33°C). Then in a second step the diastereomeric complex was in situ decomposed in the extractor (200 bar, 73°C) and the S,S-enantiomer (e.e.=61.6%, yield=31.9%) was also extracted. These results are much better than those achieved by conventional methods. Decomposition temperature of the complex (73°C) was much lower than that at atmospheric pressure (>100°C), which indicates a great advantage of the supercritical conditions. The raffinate of the fractionated extraction was reused for new resolutions without further treatment. Effects of the amount of resolving agent and extraction pressure and temperature of the first extraction step were studied in details.

Original languageEnglish
Pages (from-to)33-40
Number of pages8
JournalJournal of Supercritical Fluids
Volume31
Issue number1
DOIs
Publication statusPublished - Sep 2004

Fingerprint

Supercritical fluids
Enantiomers
supercritical fluids
enantiomers
Fractionation
fractionation
alcohols
Alcohols
Carbon Dioxide
Organic solvents
Atmospheric pressure
carbon dioxide
Carbon dioxide
atmospheric pressure
Decomposition
decomposition
Temperature
acids
temperature
Acids

Keywords

  • Carbon dioxide
  • Enantioseparation
  • Fractionated supercritical fluid extraction
  • Organic solvent free method
  • trans-2-Chloro-cyclohexan-1-ol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

Application of supercritical fluid extraction for fractionation of enantiomers. / Székely, Edit; Simándi, B.; Illés, Rita; Molnár, Péter; Gebefügi, István; Kmecz, Ildikó; Fogassy, E.

In: Journal of Supercritical Fluids, Vol. 31, No. 1, 09.2004, p. 33-40.

Research output: Contribution to journalArticle

Székely, Edit ; Simándi, B. ; Illés, Rita ; Molnár, Péter ; Gebefügi, István ; Kmecz, Ildikó ; Fogassy, E. / Application of supercritical fluid extraction for fractionation of enantiomers. In: Journal of Supercritical Fluids. 2004 ; Vol. 31, No. 1. pp. 33-40.
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