Skip to main content
Log in

Hydroisomerization of cis-Stilbene into trans-Stilbene on Supported Heterogeneous Metal Catalysts (Rh, Pd, Pt, Ru, Ir/α-Al2O3)

  • Published:
Kinetics and Catalysis Aims and scope Submit manuscript

Abstract

The hydroisomerization of a cis-isomer to produce a trans-isomer on Rh, Pd, Pt, Ru, and Ir/α-Al2O3 catalysts is studied. It is shown that Rh and Ru catalysts on which the hydroisomerization reaction mostly takes place exhibit the most favorable characteristics, whereas on the other metals, the main route is the hydrogenation reaction. Rh/α-Al2O3 is the optimum catalyst, since it has much higher activity than Ru/α-Al2O3. It is found that the increased selectivity of the trans-isomer formation is facilitated by a decrease in the hydrogen pressure and by an increase in the substrate concentration. The maximum selectivity is achieved when the reaction is carried out in nonpolar n-hexane and toluene, whereas in the case of the more polar tetrahydrofuran (THF), dimethylformamide (DMFA), and methanol both the reaction rate and the selectivity of the trans-isomer formation decline.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Paust, J. and John, M., US Patent 5689022, 1997.

    Google Scholar 

  2. Nicolaou, K.C., Daines, R.A., Chakraborty, T.K., and Ogawa, Y., J. Am. Chem. Soc., 1987, vol. 109, p. 2821.

    Article  CAS  Google Scholar 

  3. Semenov, V.V., Kiselyov, A.S., Titov, I.Y., Sagamanova, I.K., Ikizalp, N.N., Chernysheva, N.B., Tsyganov, D.V., Konyushkin, L.D., Firgang, S.I., Semenov, R.V., Karmanova, I.B., Raihstat, M.M., and Semenova, M.N., J. Nat. Prod., 2010, vol. 73, p. 1796.

    Article  CAS  Google Scholar 

  4. Mori, K., In Total Synthesis of Natural Products, Ed. J. ApSimon, New York: Wiley Interscience, 1992, vol. 9, p. 521.

    Google Scholar 

  5. Mori, K., Top. Curr. Chem., 2004, vol. 239, p. 1.

    Article  CAS  Google Scholar 

  6. Odinokov, V.N., Chem. Nat. Compd., 2000, vol. 36, p. 11.

    Article  CAS  Google Scholar 

  7. Chen, M. and Roush, W.R., Org. Lett., 2012, vol. 14, p. 1880.

    Article  CAS  Google Scholar 

  8. Fouché M., Rooney, L. and Barrett, A.G.M., Org. Chem., 2012, vol. 77, p. 3060.

    Article  Google Scholar 

  9. Oger, C., Balas, L., Durand T., and Galano J.-M, Chem. Rev., 2013, vol. 113, p. 1313.

    Article  CAS  Google Scholar 

  10. Ananikov, V.P., Khokhlova, E.A., Egorov, M.P., Sakharov, A.M., Zlotin, S.G., Kucherov, A.V., Kustov, L.M., Gening, M.L., and Nifantiev, N.E., Mendeleev Commun., 2015, vol. 25, p. 75.

    Article  CAS  Google Scholar 

  11. Keitz, B.K., Endo, K., Patel, P.R., Herbert, M.B., and Grubbs, R.H., J. Am. Chem. Soc., 2012, vol. 134, p. 693.

    Article  CAS  Google Scholar 

  12. Grubbs, R.H., Handbook of Metathesis, Wiley-CH: Weinheim, Germany, 2003, p. 1234.

    Book  Google Scholar 

  13. Trost, B.M., Ball, Z.T., and Joge, T., J. Am. Chem. Soc., 2002, vol. 124, p. 7922.

    Article  CAS  Google Scholar 

  14. Wittig, G. and Schollkopf, U., Chem. Ber., 1954, vol. 87, p. 1318.

    Article  Google Scholar 

  15. Maryanoff, B.E. and Reitz, A.B., Chem. Rev., 1989, vol. 89, p. 863.

    Article  CAS  Google Scholar 

  16. Wadsworth, W. and Emmons, W.D., J. Am. Chem. Soc., 1961, vol. 83, p. 1733.

    Article  CAS  Google Scholar 

  17. Blakemore, P.R., J. Chem. Soc., Perkin Trans., 2002, vol. 1, p. 2563.

    Article  Google Scholar 

  18. Peterson, D.J., Org. Chem., 1968, vol. 33, p. 780.

    Article  CAS  Google Scholar 

  19. Ananikov, V.P., Galkin, K.I., Egorov, M.P., Sakharov, A.M., Zlotin, S.G., Redina, E.A., Isaeva, V.I., Kustov, L.M., Gening, M.L., and Nifantiev, N.E., Mendeleev Commun., 2016, vol. 26, p. 365.

    Article  CAS  Google Scholar 

  20. Karunananda, M.K. and Mankad, N.P., J. Am. Chem. Soc., 2015, vol. 137, p. 14598.

    Article  CAS  Google Scholar 

  21. Neumann, K.T., Klimczyk, S., Burhardt, M.N., Bang-Andersen, B., Skrydstrup, T., and Lindhardt, A.T., ACS Catal., 2016, vol. 6, p. 4710.

    Article  CAS  Google Scholar 

  22. Kusy, R. and Grela, K., Org. Lett., 2016, vol. 18, p. 6196.

    Article  CAS  Google Scholar 

  23. Komatsu, T., Takagi, K., and Ozawa, K., Catal. Today, 2011, vol. 164, p. 143.

    Article  CAS  Google Scholar 

  24. Furukawa, S., Yokoyama, A., and Komatsu, T., ACS Catal., 2014, vol. 4, p. 3581.

    Article  CAS  Google Scholar 

  25. Kachala, V.V., Khemchyan, L.L., Kashin, A.S., Orlov, N.V., Grachev, A.A., Zalesskii, S.S., and Ananikov, V.P., Russ. Chem. Rev., 2013, vol. 82, p. 648.

    Article  Google Scholar 

  26. Markov, P.V., Bragina, G.O., Baeva, G.N., Tkachenko, O.P., Mashkovskii, I.S., Yakushev, I.A., Kozitsyna, N.Yu., Vargaftik, M.N, and Stakheev, A.Yu., Kinet. Catal., 2015, vol. 56, p. 591.

    Article  CAS  Google Scholar 

  27. Bond, G.C., Metal-Catalyzed Reactions of Hydrocarbons, Springer: Rickmansworth, UK, 2005, p. 666.

    Google Scholar 

  28. Kogan, V.B., Fridman, V.M., and Kafarov, V.V., Spravochnik po rastvorimosti. Binarnye sistemy (Handbook of Solubility. Binary Systems), Kafarov, V.V., Eds., vol. 1, no. 1, Moscow: Izd-vo ANSSSR, 1961, p. 959.

  29. Furukawa, S., Ochi, K., Luo, H., Miyazaki, M., and Komatsu, T., Chem. Cat. Chem., 2015, vol. 7, p. 3472.

    CAS  Google Scholar 

  30. Studer, M., Baumeister, P., Blaser, H., and Bach, J., J. Mol. Catal. A, 1995, vol. 95, p. 155.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Stakheev.

Additional information

Original Russian Text © P.V. Markov, I.S. Mashkovsky, G.N. Baeva, A.Yu. Stakheev, 2017, published in Kinetika i Kataliz, 2017, Vol. 58, No. 6, pp. 751–759.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Markov, P.V., Mashkovsky, I.S., Baeva, G.N. et al. Hydroisomerization of cis-Stilbene into trans-Stilbene on Supported Heterogeneous Metal Catalysts (Rh, Pd, Pt, Ru, Ir/α-Al2O3). Kinet Catal 58, 771–779 (2017). https://doi.org/10.1134/S0023158417060064

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0023158417060064

Keywords

Navigation