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Equilibrium Studies on Enantioselective Liquid-Liquid Amino Acid Extraction Using a Cinchona Alkaloid Extractant

Schuur, B., Winkelman, J. G. M. & Heeres, H. J., 17-Dec-2008, In : Industrial and Engineering Chemistry Research. 47, 24, p. 10027-10033 7 p.

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The enantioselective extraction of aqueous 3,5-dinitrobenzoyl-R,S-leucine (A(R,S)) by a cinchona alkaloid extractant (C) in 1,2-dichloroethane was studied at room temperature (294 K) in a batch system for a range of intake concentrations (10(-4)-10(-3) mol/L) and pH values (3.8-6.6). The experimental data were described by a reactive extraction model with a homogeneous organic phase reaction of A(R,S) with C. Important parameters of this model were determined experimentally. The acid dissociation constant, K(a), of A(R,S) was (1.92 +/- 0.07) x 10(-4) mol/L. The physical distribution coefficient of A(R,S) between the organic and aqueous phase was 8.04 +/- 0.39. The equilibrium constants of the organic phase complexation reaction were (9.31 +/- 0.76) x 104 L/mol and (2.71 +/- 0.76) x 10(4) L/mol for the S- and R-enantiomers, respectively. With these parameters an optimum performance factor, PF, of 0.19 was predicted. The PF was independent of the pH provided that pH >> pK(a). The model was verified experimentally with excellent results (+/- 7.9%).

Original languageEnglish
Pages (from-to)10027-10033
Number of pages7
JournalIndustrial and Engineering Chemistry Research
Volume47
Issue number24
Publication statusPublished - 17-Dec-2008

    Keywords

  • ENANTIO-SELECTIVE EXTRACTION, CHIRAL SEPARATION, REACTIVE EXTRACTION, DERIVATIVES, PARTITION, ALCOHOLS, ION, ENANTIOSEPARATION, CHROMATOGRAPHY, RECOGNITION

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