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Kinetics of enantioselective liquid-liquid extraction of phenylglycine enantiomers using a BINAP-copper complex as chiral selector

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Abstract

Kinetic study of reactive extraction of phenylglycine (PhgH) racemate with S-BINAP ((S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene)-copper complex (BINAP-Cu) as the chiral selector was performed in a modified Lewis cell. The theory of extraction accompanied by a chemical reaction was applied to achieve insightful understanding of the extraction process. The effects of agitation speed, interface area, pH value of the aqueous phase, initial concentration of PhgH racemate, and initial concentration of BINAP-Cu on the specific rate of extraction were investigated. An extraction course was simulated based on the rate equations. The forward rate constants of 3.14 × 10−5 m3.4 mol−0.7 s−1 for R-PhgH and 4.03 × 10−5 m3.4 mol−0.7 s−1 for S-PhgH, respectively, were found. The modeled extraction course was in good agreement with the experimental one.

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Authors and Affiliations

  1. Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, 414006, China

    Pan-Liang Zhang, Ke-Wen Tang & Jian-Min Yi

  2. College of Chemistry, Xiangtan University, Xiangtan, 411105, China

    Jing-Jing Luo, Ke-Wen Tang & Jian-Min Yi

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  1. Pan-Liang Zhang
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Correspondence to Ke-Wen Tang.

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Zhang, PL., Luo, JJ., Tang, KW. et al. Kinetics of enantioselective liquid-liquid extraction of phenylglycine enantiomers using a BINAP-copper complex as chiral selector. Chem. Pap. 68, 1317–1324 (2014). https://doi.org/10.2478/s11696-014-0571-5

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