Fast further purification of diastereomeric salts of a nonracemic acid by gas antisolvent fractionation

Márton Kőrösi, J. Madarász, Tamás Sohajda, Edit Székely

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A novel, green possibility of the further purification of the diastereomeric salt of 4-chloromandelic acid and 1-phenylethane-1-amine was developed. Gas antisolvent method using supercritical carbon dioxide was applied for the first time to precipitate the diastereomeric salts with increased purity followed by the supercritical fluid extraction of the dissolved diastereomers. The RR-salt can be purified to >99%, while fractionation-based purification of the SR-salt is limited to ~80%. The limiting initial diastereomeric excess correlates strongly with the atmospheric melting eutectic composition of the same salts, which suggests that despite the fast precipitation, the diastereomeric excess of the solid product is not kinetically determined. The efficiency of the diastereomeric enrichment is in the same range as that of the atmospheric reference experiments; however, technological advantages provided by the antisolvent precipitation method such as fast processing and dry product obtained suggest that this novel procedure is a promising alternative to the atmospheric methods.

Original languageEnglish
Pages (from-to)610-615
Number of pages6
JournalChirality
Volume29
Issue number10
DOIs
Publication statusPublished - Jan 1 2017

Keywords

  • diastereomeric salt
  • enantiomeric enrichment
  • eutectic behavior
  • melting point
  • supercritical carbon dioxide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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