Enantioseparation of ibuprofen by supercritical fluid extraction

Péter Molnár, Edit Székely, B. Simándi, S. Keszei, Judit Lovász, E. Fogassy

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

In this work influencing factors of enantioseparation of racemic ibuprofen via partial diastereomeric salt formation with R-(+)-phenylethylamine and subsequent supercritical fluid extraction (SFE) of the unreacted enantiomers were studied. It was demonstrated that conditions for diastereomeric salt formation and sample preparation (amount of resolution agent and achiral support, quality of solvent) have deep effects on SFE and on achievable resolution efficiency (F). Optimal value of the resolution agent/racemic ibuprofen molar ratio is 0.5. Addition of achiral support improves significantly the quality of the extraction bed and reduces the extraction time, but it has negligible effect on F. Solvent effects were studied using different organic solvents (acetone, dichloromethane, ethyl alcohol, ethyl acetate, methyl alcohol, methyl ethyl ketone and tetrachloromethane) and were compared to resolution in melt and suspension. It was demonstrated that solvents have important effect on F as well as on initial dissolution rates. Among SFE control parameters only pressure has significant effect on F precluding the possibility of pure density dependence.

Original languageEnglish
Pages (from-to)384-389
Number of pages6
JournalJournal of Supercritical Fluids
Volume37
Issue number3
DOIs
Publication statusPublished - May 2006

Fingerprint

Supercritical fluids
supercritical fluids
Ibuprofen
Salts
salts
Phenethylamines
Enantiomers
Carbon Tetrachloride
Methylene Chloride
enantiomers
Dichloromethane
carbon tetrachloride
Acetone
Ketones
ketones
Organic solvents
acetone
Methanol
beds
acetates

Keywords

  • Carbon dioxide
  • Enantioseparation
  • Ibuprofen
  • Sample preparation
  • Supercritical fluid extraction

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Physics and Astronomy (miscellaneous)

Cite this

Enantioseparation of ibuprofen by supercritical fluid extraction. / Molnár, Péter; Székely, Edit; Simándi, B.; Keszei, S.; Lovász, Judit; Fogassy, E.

In: Journal of Supercritical Fluids, Vol. 37, No. 3, 05.2006, p. 384-389.

Research output: Contribution to journalArticle

Molnár, Péter ; Székely, Edit ; Simándi, B. ; Keszei, S. ; Lovász, Judit ; Fogassy, E. / Enantioseparation of ibuprofen by supercritical fluid extraction. In: Journal of Supercritical Fluids. 2006 ; Vol. 37, No. 3. pp. 384-389.
@article{d3904c8d3e7f45e1a08ae2c4bdc6b0a5,
title = "Enantioseparation of ibuprofen by supercritical fluid extraction",
abstract = "In this work influencing factors of enantioseparation of racemic ibuprofen via partial diastereomeric salt formation with R-(+)-phenylethylamine and subsequent supercritical fluid extraction (SFE) of the unreacted enantiomers were studied. It was demonstrated that conditions for diastereomeric salt formation and sample preparation (amount of resolution agent and achiral support, quality of solvent) have deep effects on SFE and on achievable resolution efficiency (F). Optimal value of the resolution agent/racemic ibuprofen molar ratio is 0.5. Addition of achiral support improves significantly the quality of the extraction bed and reduces the extraction time, but it has negligible effect on F. Solvent effects were studied using different organic solvents (acetone, dichloromethane, ethyl alcohol, ethyl acetate, methyl alcohol, methyl ethyl ketone and tetrachloromethane) and were compared to resolution in melt and suspension. It was demonstrated that solvents have important effect on F as well as on initial dissolution rates. Among SFE control parameters only pressure has significant effect on F precluding the possibility of pure density dependence.",
keywords = "Carbon dioxide, Enantioseparation, Ibuprofen, Sample preparation, Supercritical fluid extraction",
author = "P{\'e}ter Moln{\'a}r and Edit Sz{\'e}kely and B. Sim{\'a}ndi and S. Keszei and Judit Lov{\'a}sz and E. Fogassy",
year = "2006",
month = "5",
doi = "10.1016/j.supflu.2005.10.009",
language = "English",
volume = "37",
pages = "384--389",
journal = "Journal of Supercritical Fluids",
issn = "0896-8446",
publisher = "Elsevier",
number = "3",

}

TY - JOUR

T1 - Enantioseparation of ibuprofen by supercritical fluid extraction

AU - Molnár, Péter

AU - Székely, Edit

AU - Simándi, B.

AU - Keszei, S.

AU - Lovász, Judit

AU - Fogassy, E.

PY - 2006/5

Y1 - 2006/5

N2 - In this work influencing factors of enantioseparation of racemic ibuprofen via partial diastereomeric salt formation with R-(+)-phenylethylamine and subsequent supercritical fluid extraction (SFE) of the unreacted enantiomers were studied. It was demonstrated that conditions for diastereomeric salt formation and sample preparation (amount of resolution agent and achiral support, quality of solvent) have deep effects on SFE and on achievable resolution efficiency (F). Optimal value of the resolution agent/racemic ibuprofen molar ratio is 0.5. Addition of achiral support improves significantly the quality of the extraction bed and reduces the extraction time, but it has negligible effect on F. Solvent effects were studied using different organic solvents (acetone, dichloromethane, ethyl alcohol, ethyl acetate, methyl alcohol, methyl ethyl ketone and tetrachloromethane) and were compared to resolution in melt and suspension. It was demonstrated that solvents have important effect on F as well as on initial dissolution rates. Among SFE control parameters only pressure has significant effect on F precluding the possibility of pure density dependence.

AB - In this work influencing factors of enantioseparation of racemic ibuprofen via partial diastereomeric salt formation with R-(+)-phenylethylamine and subsequent supercritical fluid extraction (SFE) of the unreacted enantiomers were studied. It was demonstrated that conditions for diastereomeric salt formation and sample preparation (amount of resolution agent and achiral support, quality of solvent) have deep effects on SFE and on achievable resolution efficiency (F). Optimal value of the resolution agent/racemic ibuprofen molar ratio is 0.5. Addition of achiral support improves significantly the quality of the extraction bed and reduces the extraction time, but it has negligible effect on F. Solvent effects were studied using different organic solvents (acetone, dichloromethane, ethyl alcohol, ethyl acetate, methyl alcohol, methyl ethyl ketone and tetrachloromethane) and were compared to resolution in melt and suspension. It was demonstrated that solvents have important effect on F as well as on initial dissolution rates. Among SFE control parameters only pressure has significant effect on F precluding the possibility of pure density dependence.

KW - Carbon dioxide

KW - Enantioseparation

KW - Ibuprofen

KW - Sample preparation

KW - Supercritical fluid extraction

UR - http://www.scopus.com/inward/record.url?scp=33646083942&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33646083942&partnerID=8YFLogxK

U2 - 10.1016/j.supflu.2005.10.009

DO - 10.1016/j.supflu.2005.10.009

M3 - Article

AN - SCOPUS:33646083942

VL - 37

SP - 384

EP - 389

JO - Journal of Supercritical Fluids

JF - Journal of Supercritical Fluids

SN - 0896-8446

IS - 3

ER -