Chiral Separation of Ketoprofen Enantiomers by Preparative and Simulated Moving Bed Chromatography

The pharmaceutical industry is now directed to the market of more safety and efficient drugs, based on single enantiomers. Ketoprofen, still used as a racemic pharmaceutical drug, belongs to the profens class, one of the most representative of the non-steroidal anti-inflammatory drugs. This work pre...

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Bibliographic Details
Published in:Separation science and technology 2011-07, Vol.46 (11), p.1726-1739
Main Authors: Ribeiro, António E., Gomes, Pedro Sá, Pais, Luís S., Rodrigues, Alírio E.
Format: Article
Language:English
Subjects:
Anti-inflammatory agents
Chromatography
Comparative analysis
Comparative studies
Drugs
Elution
Enantiomers
Ethanol
Ethyl alcohol
Hydrocarbons
Inflammation
Ketoprofen
n-Hexane
Nonsteroidal anti-inflammatory drugs
Optimization
Pharmaceutical industry
Pharmaceuticals
preparative chiral separation
Separation
simulated moving bed chromatography
solvent composition
Solvents
Stationary phase
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Summary:The pharmaceutical industry is now directed to the market of more safety and efficient drugs, based on single enantiomers. Ketoprofen, still used as a racemic pharmaceutical drug, belongs to the profens class, one of the most representative of the non-steroidal anti-inflammatory drugs. This work presents the chiral separation of ketoprofen enantiomers by simulated moving bed technology, using a laboratory scale unit (the FlexSMB-LSRE®) with six columns, packed with the Chiralpak AD® stationary phase (20 μm). A comparative study between a mobile phase composed of a traditional high hydrocarbon content (10%ethanol/90%n-hexane/0.01%TFA) and a strong polar organic composition (100%ethanol/0.01%TFA) is presented. The study includes the measurement of the adsorption isotherms, elution, and frontal chromatography experiments, carried out on a SMB column for both compositions. The results obtained allowed the prediction and optimization of the SMB operation. Using pure ethanol as solvent and a racemic feed concentration of 40 g/L, purities above 98.6% on both outlet streams were obtained, with a productivity of 3.84 g feed /(L bed .hr) and a solvent consumption of 0.78 L solvent /g feed . The results obtained in the experimental separation of ketoprofen enantiomers by SMB chromatography indicates that pure ethanol presents better performances than the classic high hydrocarbon content composition.
ISSN:0149-6395
1520-5754
DOI:10.1080/01496395.2011.582070