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Physicochemical study of polymer-stabilized platinum catalysts for enantioselective hydrogenation of ketones

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Abstract

Platinum-containing catalytic systems based on hyper-cross-linked polystyrene have been synthesized, and their structure has been investigated. The catalysts have been tested in the enantioselective hydrogenation of ethyl pyruvate as a model reaction. The product of this reaction—(R)-ethyl lactate—is usable as a chiral monomer in the synthesis of biodegradable polymers. The catalytic systems have been characterized by XPS, TEM, X-ray diffraction, diffuse reflectance IR spectroscopy, and low-temperature nitrogen adsorption. The formation of Pt(0) particles in the polymer matrix begins at the precursor introduction stage. The resulting active phase particles have a narrow size distribution with a peak occurring at 2 nm. The maximum enantiomeric excess attained in the test reaction is 75%. It is possible to premodify the catalyst without lowering the enantioselectivity of the hydrogenation process.

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References

  1. Davankov, V. and Tsyurupa, M., J. Chromatogr. A, 2005, vol. 1087, nos. 1–2, p. 3.

    CAS  Google Scholar 

  2. Davankov, A., Tsyurupa, M.P., and Alexienko, N.N., J. Chromatogr. A, 2005, vol. 1100, no. 1, p. 32.

    Article  CAS  Google Scholar 

  3. Sychov, C.S., Ilyin, M.M., Davankov, V.A., et al., J. Chromatogr., A, 2004, vol. 1030, p. 17.

    Article  CAS  Google Scholar 

  4. Fontanals, N. Cormack, P.A.G., et al., J. Chromatogr., A, 2005, vol. 1075, nos. 1–2, p. 51.

    CAS  Google Scholar 

  5. Fontanals, N., Marcé, R.M., Cormack, P.A.G., et al., J. Chromatogr., A, 2008, vol. 1191, nos. 1–2, p. 118.

    CAS  Google Scholar 

  6. Fontanals, N., Cormack, P.A.G., and Sherrington, D.C., J. Chromatogr., A, 2008, vol. 1215, nos. 1–2, p. 21.

    CAS  Google Scholar 

  7. Bratkowska, D., Marcé, R.M., Cormack, P.A.G., et al., J. Chromatogr., A, 2010, vol. 1217, no. 10, p. 1575.

    Article  CAS  Google Scholar 

  8. Liu, P., Long, C., Qian, H.M., et al., Chin. Chem. Lett., 2009, vol. 20, no. 4, p. 492.

    Article  CAS  Google Scholar 

  9. Chang, C.-F., Chang, C.-Y., Hsu, K.-E., et al., J. Environ. Eng. Manage., 2007, vol. 17, no. 5, p. 311.

    CAS  Google Scholar 

  10. Germain, J. Hradil, J., Fréchet J.M.J., et al., Chem. Mater., 2006, vol. 18, no. 18, p. 4430.

    Article  CAS  Google Scholar 

  11. Tsyurupa, M.P. and Davankov, V.A., React. Funct. Polym., 2006, vol. 66, no. 7, p. 768.

    Article  CAS  Google Scholar 

  12. Sulman, E.M., Matveeva, V.G., Doluda, YuV., et al., Appl. Catal., B, 2010, vol. 94, p. 200.

    Article  CAS  Google Scholar 

  13. Nikoshvili, L.Zh., Doluda, V.Yu., and Sul’man, E.M., Vestn. MITKhT, 2009, vol. 4, no. 2, p. 95.

    Google Scholar 

  14. Sidorov, S.N., Volkov, I.V., Davankov, V.A., et al., J. Am. Chem. Soc., 2001, vol. 123, no. 43, p. 10502.

    Article  CAS  Google Scholar 

  15. Matveeva, V., Bykov, A., Doluda, V., et al., Top. Catal., 2009, vol. 52, p. 387.

    Article  CAS  Google Scholar 

  16. Valetskii, P.M., Sul’man, M.G., Bronshtein, L.M., et al., Ross. Nanotekhnol., 2009, nos. 9–10, p. 94.

  17. Nikoshvili, L.Z., Sulman, E.M., Demidenko, G.N., et al., in Catalysis of Organic Reactions, Schmidt, S.R., Ed., Boca Raton, Fla.: CRC, 2007, p. 177.

    Google Scholar 

  18. Coloma, F., Sepulveda-Escribano, A., Fierro, J.L.G., et al., Langmuir, 1994, vol. 10, no. 3, p. 750.

    Article  CAS  Google Scholar 

  19. Labinger, J.A., Herring, A.M., and Bercaw, J.E., J. Am. Chem. Soc., 1990, vol. 112, no. 14, p. 5628.

    Article  CAS  Google Scholar 

  20. Sen, A., Lin, M., Kao, L.C., et al., J. Am. Chem. Soc., 1992, vol. 114, no. 16, p. 6385.

    Article  CAS  Google Scholar 

  21. Shi, M., J. Chem. Res., Synop., 1998, vol. 9, p. 592.

    Article  Google Scholar 

  22. Margitfalvi, J.L., Hegedüs, M., and Tfirst, E., Tetrahedron: Asymmetry, 1996, vol. 7, no. 2, p. 571.

    Article  CAS  Google Scholar 

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Original Russian Text © A.V. Bykov, M.B. Konyaeva, G.N. Demidenko, V.G. Matveeva, I.Yu. Tyamina, E.M. Sul’man, 2012, published in Kataliz v Promyshlennosti.

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Bykov, A.V., Konyaeva, M.B., Demidenko, G.N. et al. Physicochemical study of polymer-stabilized platinum catalysts for enantioselective hydrogenation of ketones. Catal. Ind. 4, 340–346 (2012). https://doi.org/10.1134/S207005041204006X

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  • DOI: https://doi.org/10.1134/S207005041204006X

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