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Enantioselective extraction of mandelic acid enantiomers by L-dipentyl tartrate and β-cyclodextrin as binary chiral selectors

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Abstract

A new binary chiral selector system effective for the enantioselective extraction of racemic mandelic acid is presented. While L-dipentyl tartrate and β-cyclodextrin had a very low enantioselectivity as single selectors, a preferential extraction of D-mandelic acid to the organic phase was found in the binary selector system. Using decanol as organic solvent and pH of a phoshate buffer equal to 2.3, the distribution coefficients of D-and L-mandelic acids as high as 14.9 and 7.0, respectively, and the enantioselectivity value of 2.1 were found at optimum concentration of β-cyclodextrin.

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References

  1. Lacour, J., Goujon-Ginglinger, C., Torche-Haldimann, S., and Jodry, J. J., Angew. Chem., Int. Ed. Engl. 39, 3695 (2000).

    Article  CAS  Google Scholar 

  2. Subramanian, G., Chiral Separation Techniques: A Practical Approach, p. 15. Wiley, New York, 2001.

    Google Scholar 

  3. Zhao, S. L. and Liu, Y. M., Electrophoresis 22, 2769 (2001).

    Article  PubMed  CAS  Google Scholar 

  4. Heldin, E., Lindner, K. J., Pettersson, C., Lindner, W., and Rao, R., Chromatographia 32, 407 (1991).

    Article  CAS  Google Scholar 

  5. Keurentjes, J. T. F., Nabuurs, L. J. W. M., and Vegeter, E. A., J. Membr. Sci. 113, 351 (1996).

    Article  CAS  Google Scholar 

  6. Tan, B., Luo, G. S., Xuan, Q., and Wang, J. D., Sep. Purif. Technol. 49, 186 (2006).

    Article  CAS  Google Scholar 

  7. Tan, B., Luo, G. S., and Wang, J. D., Tetrahedron: Asymmetry 17, 883 (2006).

    Article  CAS  Google Scholar 

  8. Li, B. H., Yang, X. M., Wu, X. J., Luo, Z. W., Zhong, C., and Fu, E., Supramol. Chem. 18, 507 (2006).

    Article  CAS  Google Scholar 

  9. Armstrong, D. W. and Jin, H. L., Anal. Chem. 59, 2237 (1987).

    Article  PubMed  CAS  Google Scholar 

  10. Szemán, J. and Ganzler, K., J. Chromatogr., A 668, 509 (1994).

    Article  Google Scholar 

  11. Jiao, F. P., Huang, K. L., Ning, F. R., Hu, W. G., and Yu, J. G., Sep. Sci. Technol. 41, 1893 (2006).

    Article  CAS  Google Scholar 

  12. Arai, T., Koike, H., Hirata, K., and Oizumi, H., J. Chromatogr. 448, 439 (1988).

    Article  PubMed  CAS  Google Scholar 

  13. Prelog, V., Stojanac, Z., and Kovacevic, K., Helv. Chim. Acta 65, 377 (1982).

    Article  CAS  Google Scholar 

  14. Prelog, V. and Mutak, S., Helv. Chim. Acta 66, 2274 (1983).

    Article  CAS  Google Scholar 

  15. Prelog, V., Kovacevic, M., and Egli, M., Angew. Chem., Int. Ed. Engl. 28, 1147 (1989).

    Article  Google Scholar 

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Authors and Affiliations

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

    F. P. Jiao, X. Q. Chen, W. G. Hu, F. R. Ning & K. L. Huang

  2. School of Chemical Engineering, Xiangtan University, Xiangtan, 411105, China

    F. P. Jiao

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  1. F. P. Jiao
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  2. X. Q. Chen
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  3. W. G. Hu
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  4. F. R. Ning
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  5. K. L. Huang
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Jiao, F.P., Chen, X.Q., Hu, W.G. et al. Enantioselective extraction of mandelic acid enantiomers by L-dipentyl tartrate and β-cyclodextrin as binary chiral selectors. Chem. Pap. 61, 326–328 (2007). https://doi.org/10.2478/s11696-007-0041-4

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  • DOI: https://doi.org/10.2478/s11696-007-0041-4

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