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Enantioseparation of 2‐(4‐chlorophenyl)succinic acid by countercurrent chromatography and investigation of injection volume on resolution
Author(s) -
Jin Yang,
Bao Honglei,
Sun Wenyu,
Sun Hengmian,
Zhao Shanshan,
Wang Xiang,
Tong Shengqiang
Publication year - 2021
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.202000860
Subject(s) - chromatography , chemistry , succinic acid , countercurrent chromatography , resolution (logic) , volume (thermodynamics) , solvent , enantiomer , high performance liquid chromatography , inflection point , tartaric acid , countercurrent exchange , quantitative analysis (chemistry) , organic chemistry , citric acid , physics , quantum mechanics , artificial intelligence , computer science , thermodynamics , geometry , mathematics
2‐(4‐Chlorophenyl)succinic acid was successfully enantioseparated by countercurrent chromatography using hydroxypropyl‐β‐cyclodextrin as chiral selector. A two‐phase solvent system composed of n ‐hexane‐ethyl acetate‐0.1 mol/L phosphate buffer with pH 2.65 (5:5:10, v/v) was selected. Enantioselective liquid–liquid extraction was used to optimize the enantioseparation conditions. Meanwhile, the influence of injection volume on resolution in countercurrent chromatography was investigated and a linear relationship between the inflection point of injection volume and sample loading was tentatively obtained. The peak resolution will decrease significantly when the injection volume over the inflection point was used. In addition, it could be found that the smaller amount of sample loading, the larger impact of injection volume on resolution could be observed, which might serve as a good reference for the selection of sample volume in enantioseparations by countercurrent chromatography. Under optimized conditions, 20 mg of 2‐(4‐chlorophenyl)succinic acid racemate dissolved in 10 mL of aqueous phase was successfully enantioseparated by countercurrent chromatography. The recovery for both of the enantiomer of (±)‐2‐(4‐chlorophenyl)succinic acid reached within 70–75% with a purity of 99.0%.