Application of mixtures of tartaric acid derivatives in resolution via supercritical fluid extraction

Ildikó Kmecz, B. Simándi, Edit Székely, Judit Lovász, E. Fogassy

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Racemic N-methylamphetamine (rac-MA) was resolved with 2R,3R-tartaric acid (TA) and its derivatives (O,O′-dibenzoyl-(2R,3R)-tartaric acid monohydrate (DBTA) and O,O′-di-p-toluoyl-(2R,3R)-tartaric acid (DPTTA)), individually and using them in different combinations. After partial diastereomeric salt formation, the free enantiomers were extracted by supercritical fluid extraction using carbon dioxide as solvent. DBTA and DPTTA are efficient resolving agents for rac-MA, the best chiral separation being obtained at a molar ratio of 0.25 resolving agent to racemic compound for both resolving agents (eeE = 82.5% and eeE = 57.9%, respectively). Compared with the two other acids, TA is practically unsuitable for enantiomer separation (eeE <5%). Applying a mixture of one individually active and one ineffective acid in half the equivalent molar ratio, when the acids are in 1:1 ratio in the mixture, the resolution efficiency values obtained exceeded those obtained by using the components individually. Decreasing the molar ratio of resolving agent mixture to 0.25, at which the individual resolving agents give the best chiral separation, the obtained resolution efficiency values did not differ significantly from those expected. The outcome of the resolution process depended only on the amount of the individually active resolving agents in the mixture.

Original languageEnglish
Pages (from-to)430-433
Number of pages4
JournalChirality
Volume19
Issue number6
DOIs
Publication statusPublished - 2007

Fingerprint

Supercritical Fluid Chromatography
Supercritical fluids
Derivatives
Methamphetamine
Acids
Enantiomers
Carbon Dioxide
Salts
tartaric acid
Carbon dioxide

Keywords

  • Carbon dioxide
  • Enantiomer separation
  • Mixture of related structure resolving agents
  • Nonlinear behavior
  • Supercritical fluid extraction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Application of mixtures of tartaric acid derivatives in resolution via supercritical fluid extraction. / Kmecz, Ildikó; Simándi, B.; Székely, Edit; Lovász, Judit; Fogassy, E.

In: Chirality, Vol. 19, No. 6, 2007, p. 430-433.

Research output: Contribution to journalArticle

Kmecz, Ildikó ; Simándi, B. ; Székely, Edit ; Lovász, Judit ; Fogassy, E. / Application of mixtures of tartaric acid derivatives in resolution via supercritical fluid extraction. In: Chirality. 2007 ; Vol. 19, No. 6. pp. 430-433.
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