Resolution of α-cyclohexyl-mandelic acid enantiomers by two-phase (O/W) recognition chiral extraction |
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Authors: | TANG KeWen ZHANG GuoLi HUANG KeLong LI Yuanjian YI JianMin |
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Institution: | 1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414000, China;College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China 2. College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China 3. College of Pharmaceutical Science, Central South University, Changsha 410078, China |
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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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Keywords: | two-phase(W/O) recognition chiral extraction |
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