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Chiral separation of α-cyclohexylmandelic acid enantiomers using ionic liquid/salt aqueous two-phase system

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Abstract

In this paper, an ionic liquid-based aqueous two-phase system (ILATPS) was applied to the chiral separation of α-cyclohexylmandelic acid (α-CHMA) enantiomers with hydroxypropyl-β-cyclodextrin (HP-β-CD) as the chiral selector. Several influencing parameters were investigated including the types and concentration of ionic liquids, the amount of phase-forming salt, temperature, mixing time, pH, and the content of HP-β-CD. The results showed that not all ILATPS had the ability to chirally recognise the selected enantiomers and that [C4mim]BF4/(NH4)2SO4-based ATPS possessed the best enantioseparation ability of the investigated ILATPSs. Under optimal conditions, the separation factor (α) attained 1.59 in a single-step extraction. ILATPS is much “greener” than other liquid-liquid extraction systems, showing its potential for application to the chiral separation.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China

    Lei-Lei Chen & Fen-Fang Li

  2. Institute of Bast Fibre Crops, Chinese Academy of Agricultural Sciences, Changsha, 410205, China

    Zhi-Jian Tan

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  1. Lei-Lei Chen
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  2. Fen-Fang Li
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  3. Zhi-Jian Tan
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Correspondence to Fen-Fang Li.

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Chen, LL., Li, FF. & Tan, ZJ. Chiral separation of α-cyclohexylmandelic acid enantiomers using ionic liquid/salt aqueous two-phase system. Chem. Pap. 69, 1465–1472 (2015). https://doi.org/10.1515/chempap-2015-0162

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