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Advisor(s)
Abstract(s)
This study presents the chiral resolution of flurbiprofen enantiomers by preparative
liquid chromatography using the simulated moving bed (SMB) technology. Flurbiprofen
enantiomers are widely used as nonsteroidal anti-inflammatory drugs, and although demonstrate
different therapeutic actions, they are still marketed as a racemic mixture. The results
presented here clearly show the importance of the selection of the proper solvent composition
for the preparative separation of flurbiprofen enantiomers. Chiral SMB separation is carried
out using a laboratory-scale unit (the FlexSMB-LSRE1) with six columns, packed with the
Chiralpak AD1 stationary phase (20 lm). Results presented include the experimental measurement
of equilibrium and kinetic data for two very different solvent compositions, a traditional
high hydrocarbon content [10%ethanol/90%n-hexane/0.01% trifluoroacetic acid (TFA)] and a
strong polar organic composition (100%ethanol/0.01%TFA). Experimental data, obtained using
the two mobile phase compositions, are used to predict and optimize the SMB operation. After
selecting 10%ethanol/90%n-hexane/0.01%TFA as the most appropriate solvent composition,
three feed concentrations of racemic flurbiprofen were considered. Using 40 g/l of racemic flurbiprofen
feed solution, the purities for both outlet streams were above 99.4%, the productivity
was 13.1 gfeed/(Lbed h), and a solvent consumption of 0.41 Lsolvent/gfeed was achieved.
Description
Keywords
Chiral separations Pharmaceutical intermediate Flurbiprofen enantiomers Preparative chiral separation Simulated moving bed chromatography
Citation
Ribeiro, António E.; Gomes, Pedro Sá; Pais, L.S.; Rodrigues, Alírio E. (2011). Chiral separation of flurbiprofen enantiomers by preparative and simulated moving bed chromatography. Chirality. ISSN 0899-0042. 23:8, p. 602-611
Publisher
Wiley-Blackwell