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-LSRE1) with six columns,
packed with the Chiralpak AD1 stationary phase (20 lm).
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 gfeed=(Lbed.hr)
and a solvent consumption of 0.78Lsolvent=gfeed. 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.
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.
