Resolution of ibuprofen with primary amine carbamates in supercritical carbon dioxide

László Lőrincz, Zsolt Hovonyecz, J. Madarász, Erzsébet Varga, Edit Székely

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Three new, successful resolving agents, namely (S)-2-phenylglycinol, (R)-1-phenylethanaminium (R)-(1-phenylethyl) carbamate and (S)-2-hydroxy-1-phenylethanaminium (S)-(2-hydroxy-1-phenylethyl) carbamate of ibuprofen are presented. The carbamate salts are stable white crystals, they can be easily stored and handled. All salt forming resolution were performed in supercritical carbon dioxide as the only solvent. The enantioseparations were efficient (approx. 50 % enantiomeric purities, < 90 % yields in the crystalline phase) and robust. Unlike previous experiences with primary amine resolving agents, the diastereomeric salt formations and resolutions were competed in short times, even within one hour suggesting that the carbamates are intermediates of the salt formation reaction.

Original languageEnglish
Pages (from-to)312-317
Number of pages6
JournalPeriodica Polytechnica Chemical Engineering
Volume63
Issue number2
DOIs
Publication statusPublished - Jan 1 2019

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Carbamates
Ibuprofen
Carbon Dioxide
Amines
Carbon dioxide
Salts
Crystalline materials
Crystals

Keywords

  • Activation
  • Carbamate
  • Chiral
  • Chiral separation
  • Salt formation
  • Supercritical carbon dioxide

ASJC Scopus subject areas

  • Chemical Engineering(all)

Cite this

Resolution of ibuprofen with primary amine carbamates in supercritical carbon dioxide. / Lőrincz, László; Hovonyecz, Zsolt; Madarász, J.; Varga, Erzsébet; Székely, Edit.

In: Periodica Polytechnica Chemical Engineering, Vol. 63, No. 2, 01.01.2019, p. 312-317.

Research output: Contribution to journalArticle

Lőrincz, László ; Hovonyecz, Zsolt ; Madarász, J. ; Varga, Erzsébet ; Székely, Edit. / Resolution of ibuprofen with primary amine carbamates in supercritical carbon dioxide. In: Periodica Polytechnica Chemical Engineering. 2019 ; Vol. 63, No. 2. pp. 312-317.
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