Enantioselective separation of ketoconazole enantiomers by membrane extraction

Wang, Zhao; Cai, Changqun; Lin, Yongtao; Bian, Yongru; Hongqin, Guo; Chen, Xiaoming

doi:10.1016/j.seppur.2011.03.013

Cited by 39 publications

(21 citation statements)

References 55 publications

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“…They generally show higher solubility in the aqueous solution and better enantiorecognition than native β-cyclodextrin for any class of enantiomers. In recent years many papers have been reported about their applications as chiral selector in various kinds of chiral separation methods, such as HPLC with chiral mobile phase additive [3-9], enantioselective liquid-liquid extraction [10,11], membrane separation [12], capillary electrophoresis [13,14], etc. In our previous studies, several aromatic carboxylic acids were enantioseparated by high speed countercurrent chromatography using HP-β-CD as a chiral selector in the two-phase solvent system, where strong chiral recognition was observed [15-18].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation

Tong

Zhang

Shen

et al. 2014

Journal of Chromatography B

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The enantioseparation of ten mandelic acid derivatives was performed by reverse phase high performance liquid chromatography with hydroxypropyl-β-cyclodextrin (HP-β-CD) or sulfobutyl ether-β-cyclodextrin (SBE-β-CD) as chiral mobile phase additives, in which inclusion complex formations between cyclodextrins and enantiomers were evaluated. The effects of various factors such as the composition of mobile phase, concentration of cyclodextrins and column temperature on retention and enantioselectivity were studied. The peak resolutions and retention time of the enantiomers were strongly affected by the pH, the organic modifier and the type of β-cyclodextrin in the mobile phase, while the concentration of buffer solution and temperature had a relatively low effect on resolutions. Enantioseparations were successfully achieved on a Shimpack CLC-ODS column (150×4.6 mm i.d., 5 μm). The mobile phase was a mixture of acetonitrile and 0.10 mol L-1 of phosphate buffer at pH 2.68 containing 20 mmol L-1 of HP-β-CD or SBE-β-CD. Semi-preparative enantioseparation of about 10 mg of α-cyclohexylmandelic acid and α-cyclopentylmandelic acid were established individually. Cyclodextrin-enantiomer complex stoichiometries as well as binding constants were investigated. Results showed that stoichiomertries for all the inclusion complex of cyclodextrin-enantiomers were 1:1.

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Section: Introductionmentioning

confidence: 99%

Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation

Tong

Zhang

Shen

et al. 2014

Journal of Chromatography B

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“…The ELLE was investigated in countercurrent flow during the past years in different devices, such as membranes and centrifugal extractors . But the high amount of required extraction stages for a complete separation demonstrates the necessity of efficient equipment with many equilibrium stages.…”

Section: Methodsmentioning

confidence: 99%

“…However, chromatography columns are inflexible for multipurpose applications and expensive depending on acquisition and cost of operation. Furthermore, there are several emerging techniques for the separation of racemic mixtures for analytical and preparative applications, such as catalyzed conversion of the racemic mixture to the pure enantiomer, membranes, capillary electrophorese, and the enantioselective liquid–liquid extraction (ELLE) . Compared to current techniques, the ELLE is a promising alternative to realize a continuous and flexible process .…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of chiral aromatic acids in process intensified liquid–liquid extraction columns

et al. 2014

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Enantioselective liquid-liquid extraction (ELLE) is a powerful alternative to common technologies for separation of racemic mixtures. The first application of ELLE for aromatic acids in liquid-liquid extraction columns is described. The ELLE is investigated experimentally and theoretically for phenylsuccinic acid (PSA) as a representative for aromatic acids. A racemic mixture of (R/S)-PSA is separated with hydroxypropyl-b-cyclodextrin as selector molecule. The ELLE obtained the highest operative selectivity (a op 5 1.8-2) for low pH-values and temperatures. Because of the low operative selectivity, a countercurrent process is necessary to separate both enantiomers completely. The countercurrent process is investigated in process intensified extraction columns (Ø in 5 15 mm) with a high number of equilibrium stages. The experiments demonstrate a good symmetric separation with an enantiomeric excess of 60% and yields of 80% for both enantiomers. Finally, the back extraction is investigated to recycle the selector molecule and increase the efficiency.

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“…77 A new process has been developed in 2011 to separate ketoconazole enantiomers using biphasic membrane extraction. 78 A hydrophobic (L-isopentyl tartrate) and a hydrophilic (sulfobutylether--cyclodextrin) chiral selector were used, reaching a selectivity of up to 1.28. The hydrophobic PVDF membrane is permeable to the ketoconazole enantiomers but non-permeable for the chiral selectors.…”

Section: Supported Liquid Membranesmentioning

confidence: 99%

Enantioseparation with liquid membranes

Gössi

Riedl

Schuur

2017

J of Chemical Tech & Biotech

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Chiral resolution of racemic products is a challenging and important task in the pharmaceutical, agrochemical, flavor, polymer and fragrances industries. One of the options for these challenging separations is to use liquid membranes. Although liquid membranes have been known for almost four decades and have been used for optical resolutions, no comprehensive review has been published about the use of this technology for enantioseparations. In this review, the various liquid membrane‐related technologies are described and compared, including bulk liquid membranes, emulsion liquid membranes, micelle‐extraction and micellar enhanced ultrafiltration, as well as supported liquid membranes. Next to technological advances, an overview of recent developments in chiral recognition chemistry in liquid–liquid equilibria is presented. The following extractant classes have recently been reported in conjunction with chiral separation: cyclodextrines, BINOL's, calixarenes, crown ethers, BINAP's, tartaric acids and ionic liquids. The use of two supported (non‐liquid) membranes with an inner loop of extract phase appears to be the most stable liquid membrane configuration, allowing for a large degree of freedom in operational conditions such as solvent to feed ratio. The library of solvents still needs broadening to make the technology more versatile and based on the variety of successes with catalytically active organometallic complexes, development of new chiral selector systems based on asymmetric catalysis literature is suggested for future selector screening studies. © 2017 Society of Chemical Industry

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Enantioselective separation of ketoconazole enantiomers by membrane extraction

Cited by 39 publications

References 55 publications

Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation

Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation

Enantioseparation of chiral aromatic acids in process intensified liquid–liquid extraction columns

Enantioseparation with liquid membranes

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