Cui, X, Ding, Q, Shan, R-N et al. (2 more authors) (2019) Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid‐liquid extraction. Chirality, 31 (6). pp. 457-467. ISSN 0899-0042
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2019 Wiley Periodicals, Inc. This is the peer reviewed version of the following article: Cui, X, Ding, Q, Shan, R‐N, He, C‐H, Wu, K‐J. Enantioseparation of flurbiprofen enantiomers using chiral ionic liquids by liquid‐liquid extraction. Chirality. 2019; 31: 457– 467, which has been published in final form at https://doi.org/10.1002/chir.23071. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. Uploaded in accordance with the publisher's self-archiving policy. |
Keywords: | amino acid ionic liquid; chiral separation; flurbiprofen; liquid‐liquid extraction; reverse extraction |
Dates: |
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Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Engineering & Physical Sciences (Leeds) > School of Chemical & Process Engineering (Leeds) |
Depositing User: | Symplectic Publications |
Date Deposited: | 31 May 2019 13:24 |
Last Modified: | 07 May 2020 00:39 |
Status: | Published |
Publisher: | Wiley |
Identification Number: | 10.1002/chir.23071 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:146714 |