Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid-liquid extraction.

Abstract:

:Flurbiprofen is a kind of nonsteroidal anti-inflammatory drug, which has been widely used in clinic for treatment of rheumatoid arthritis and osteoarthritis. It has been reported that S-flurbiprofen shows good performance on clinic anti-inflammatory treatment, while R-enantiomer almost has no pharmacological activities. It has important practical values to obtain optically pure S-flurbiprofen. In this work, chiral ionic liquids, which have good structural designability and chiral recognize ability, were selected as the extraction selector by the assistance of quantum chemistry calculations. The distribution behaviors of flurbiprofen enantiomers were investigated in the extraction system, which was composed of organic solvent and aqueous phase containing chiral ionic liquid. The results show that maximum enantioselectivity up to 1.20 was attained at pH 2.0, 25°C using 1,2-dichloroethane as organic solvent, 1-butyl-3-methylimidazole L-tryptophan ([Bmim][L-trp]) as chiral selector. The racemic flurbiprofen initial concentration was 0.2 mmol L-1 , and [Bmim][L-trp] concentration was 0.02 mol L-1 . Furthermore, the recycle of chiral ionic liquids has been achieved by reverse extraction process of the aqueous phase with chiral selector, which is significant for industrial application of chiral ionic liquids and scale-up of the extraction process.

journal_name

Chirality

journal_title

Chirality

authors

Cui X,Ding Q,Shan RN,He CH,Wu KJ

doi

10.1002/chir.23071

subject

Has Abstract

pub_date

2019-06-01 00:00:00

pages

457-467

issue

6

eissn

0899-0042

issn

1520-636X

journal_volume

31

pub_type

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