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Enantioseparation of mandelic acid and α-cyclohexylmandelic acid using an alcohol/salt-based aqueous two-phase system

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Abstract

An alcohol/salt-based aqueous two-phase system (ATPS) was employed for enantioseparation of (R,S)-mandelic acid (MA) and (R,S)-α-cyclohexylmandelic acid (α-CHMA). Sulfonated β-cyclodextrin (Sf-β-CD) with different degrees of substitution (DS) was considered as the chiral selector. The ethanol/(NH4)2SO4 system showed the optimal chiral recognition ability for MA. To optimize the experimental conditions, Sf-β-CD concentration, ethanol and salt concentration, temperature, and pH were studied. The recognition ability of enantiomers was mainly dependent on the type of the chiral selector but the ethanol and (NH4)2SO4 concentrations also had significant influence on the enantiomeric recognition. The maximum values of α and ee up of 1.69 and 16.3 % were obtained, respectively, for MA under the optimal conditions. A potential application of this alcohol/salt ATPS is the scale-up of chiral separation of MA.

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Authors and Affiliations

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

    Fen-Fang Li, Zhi-Jian Tan & Zhi-Feng Guo

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

    Zhi-Jian Tan

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  1. Fen-Fang Li
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  2. Zhi-Jian Tan
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  3. Zhi-Feng Guo
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Correspondence to Fen-Fang Li.

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Li, FF., Tan, ZJ. & Guo, ZF. Enantioseparation of mandelic acid and α-cyclohexylmandelic acid using an alcohol/salt-based aqueous two-phase system. Chem. Pap. 68, 1539–1545 (2014). https://doi.org/10.2478/s11696-014-0594-y

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