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Resolution of α-cyclohexyl-mandelic acid enantiomers by two-phase (O/W) recognition chiral extraction

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Abstract

This paper presents a new chiral separation technology: two-phase (O/W) recognition chiral extraction. Distribution behavior of α-cyclohexyl-mandelic acid enantiomers was studied in the extraction system with D(L)-isobutyl tartrate in 1,2-dichloroethane organic phase and β-CD derivatives in aqueous phase, and the influence of the kind and concentration of extractant and pH on extraction performance was investigated. The experimental results indicate that two-phase (O/W) recognition chiral extraction is of strong chiral separation ability. HP-β-CD, HE-β-CD and Me-β-CD have higher recognition ability for S-CHMA than that for R-CHMA, among which HP-β-CD has the strongest ability; whereas, D-isobutyl tartrate has reversed recognition ability for them. In the extraction system containing HP-β-CD and D-isobutyl tartrate, e.e.% of S-CHMA in aqueous phase reached 27.6% by one stage extraction, and the distribution ratio for R-CHMA(k R ) and for S-CHMA(k s ) and separation factor (α) are 2.44, 0.89 and 2.49, respectively. Meanwhile, pH and concentration of extractant have great effects on chiral separation ability. Two-phase (O/W) recognition chiral extraction has great significance for preparative separation of racemic compounds.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414000, China

    Tang KeWen & Yi JianMin

  2. College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China

    Tang KeWen, Zhang GuoLi, Huang KeLong & Yi JianMin

  3. College of Pharmaceutical Science, Central South University, Changsha, 410078, China

    Li Yuanjian

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  1. Tang KeWen
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  2. Zhang GuoLi
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  3. Huang KeLong
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  4. Li Yuanjian
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  5. Yi JianMin
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Correspondence to Huang KeLong.

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Supported by the National Natural Science Foundation of China (Grant No. 20776038)

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Tang, K., Zhang, G., Huang, K. et al. Resolution of α-cyclohexyl-mandelic acid enantiomers by two-phase (O/W) recognition chiral extraction. Sci. China Ser. B-Chem. 50, 764–769 (2007). https://doi.org/10.1007/s11426-007-0053-5

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  • DOI: https://doi.org/10.1007/s11426-007-0053-5

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