Chiral resolution of racemic cyclopropanecarboxylic acids in supercritical carbon dioxide

Dánie Varga, György Bánsághi, Jorge Agustín Martínez Pérez, Sándor Miskolczi, L. Hegedûs, B. Simándi, Edit Székely

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The chiral resolution of two racemic cyclopropanecarboxylic acids with the resolving agents (S)-2-(N-benzylamino)butan-1-ol and (R)-1-phenylethanamine was investigated. The resolutions were based on diastereomer salt crystallization in supercritical carbon dioxide. Unreacted compounds were removed by an extraction step. Experiments were performed in a continuously stirred tank reactor and good enantioselectivities were obtained in a single step. Pressure, temperature, and density were found to strongly affect both the optical purity and the selectivity of the resolutions. The crystal structures of the formed diastereomer salts were also studied via X-ray diffraction.

Original languageEnglish
Pages (from-to)1885-1890
Number of pages6
JournalChemical Engineering and Technology
Volume37
Issue number11
DOIs
Publication statusPublished - Nov 1 2014

Fingerprint

Carbon Dioxide
Carbon dioxide
Salts
Acids
Enantioselectivity
Crystallization
Crystal structure
X ray diffraction
Experiments
Temperature
cyclopropanecarboxylic acid
1-phenethylamine

Keywords

  • Chiral resolution
  • Diastereomer salt formation
  • Enantiomer separation
  • Supercritical carbon dioxide

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)
  • Industrial and Manufacturing Engineering

Cite this

Chiral resolution of racemic cyclopropanecarboxylic acids in supercritical carbon dioxide. / Varga, Dánie; Bánsághi, György; Pérez, Jorge Agustín Martínez; Miskolczi, Sándor; Hegedûs, L.; Simándi, B.; Székely, Edit.

In: Chemical Engineering and Technology, Vol. 37, No. 11, 01.11.2014, p. 1885-1890.

Research output: Contribution to journalArticle

Varga, Dánie ; Bánsághi, György ; Pérez, Jorge Agustín Martínez ; Miskolczi, Sándor ; Hegedûs, L. ; Simándi, B. ; Székely, Edit. / Chiral resolution of racemic cyclopropanecarboxylic acids in supercritical carbon dioxide. In: Chemical Engineering and Technology. 2014 ; Vol. 37, No. 11. pp. 1885-1890.
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