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Enantioselective Partitioning of Racemic Ibuprofen in a Biphasic Recognition Chiral Extraction System
Author(s) -
Tang Kewen,
Song Litao,
Pan Yang,
Jiang Xinyu,
Miao Jiabing
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090026
Subject(s) - chemistry , enantiomer , tartrate , enantioselective synthesis , extraction (chemistry) , ibuprofen , aqueous solution , cyclodextrin , aqueous two phase system , chromatography , phase (matter) , derivative (finance) , organic chemistry , combinatorial chemistry , catalysis , medicine , pharmacology , financial economics , economics
Enantioselective partitioning of ibuprofen enantiomers in a biphasic recognition chiral extraction system was studied. A combination of hydrophobic L ‐isobutyl tartrate in organic phase and hydrophilic β ‐cyclodextrin derivative in aqueous phase is necessary to establish a biphasic recognition chiral extraction system. The studies performed involve an enantioselective extraction in a biphasic system, where ibuprofen enantiomers form four complexes with the β ‐cyclodextrin derivative in aqueous phase and the D ( L )‐isobutyl tartrate in organic phase, respectively. In these biphasic resolutions, the types and the concentrations of the extractants, pH and temperature all exert a considerable influence on the biphasic recognition process. Good enantioselectivities for ibuprofen enantiomers were obtained at pH≦2.5 and a ratio of 2:1 of [ L ‐isobutyl tartrate] to [HP‐ β ‐CD]. Biphasic recognition chiral extraction is of strong chiral separation ability, and may be very helpful to optimize the extraction systems and realize the large‐scale production of enantiomers.