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A Hydrophobic Gel for Epoxidation of Olefins with Organic Peroxides

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Abstract

The epoxidation of cyclooctene by tert-butyl hydroperoxide (t-BuOOH) over a TiO2–SiO2 xerogel made from a permethylated cyclooligosiloxane, tetraethylorthosilicate, and a Ti chloroalkoxide, was carried out in acetonitrile as the reaction solvent. The organic moieties of the hybrid gel (in this case, –CH3 groups) and the Ti content of the catalyst appear to be stable on prolonged exposure to the reaction medium. Besides very good stability, the hybrid catalyst in this study displays 100% selectivity toward cyclooctene epoxide production. Solid state 29Si magic angle spinning NMR (29Si MASNMR), diffuse reflectance Fourier transform infrared spectroscopy (DRIFTS), and chemical analysis were used to monitor the stability of the hybrid material. The kinetics of olefin epoxidation was studied in a batch reactor in the 313–343 K range.

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References

  1. M. Taramasso, G. Perego and B. Notari, US Patent 4 (1983) 410501.

  2. M. Buechler-Skoda, R. Gill, D. Vu, C. Nguyen and G. Larsen, Appl. Catal. A 185 (1999) 301.

    Google Scholar 

  3. T. Blasco, A. Corma, M.T. Navarro and J.O. Pariente, J. Catal. 156 (1995) 65.

    Google Scholar 

  4. A. Corma, Chem. Rev. 97 (1997) 2373.

    Google Scholar 

  5. J.C. van der Waal, M.S. Rigutt and H. van Bekkum, Appl. Catal. A 167 (1998) 331.

    Google Scholar 

  6. C. Sanchez and F. Ribot, New J. Chem. 18 (1994) 1007.

    Google Scholar 

  7. U. Schubert, New J. Chem. 18 (1994) 1049.

    Google Scholar 

  8. E. Lotero, D. Vu, C. Nguyen, C. Wagner and G. Larsen, Chem. Matter 10 (1998) 3756.

    Google Scholar 

  9. I.W.C.E. Arends, R.A. Sheldon, M. Wallau and U. Schchardt, Angew. Chem. 36 (1997) 1144.

    Google Scholar 

  10. D.L. Vanoppen, D.E. De Vos, M.J. Genet, P.G. Rouxhet and P.A. Jacobs, Angew. Chem. 34 (1995) 560.

    Google Scholar 

  11. J.M. Fraile, J.I. Garcia, J.A. Mayoral and E. Vispe, J. Catal. 189 (2000) 40.

    Google Scholar 

  12. S.A. Holmes, F. Quignard, A. Choplin, R. Teissier and J. Kervennal, J. Catal. 176 (1998) 173.

    Google Scholar 

  13. D. Vu, M.S. thesis, University of Nebraska-Lincoln (1999).

  14. G. Larsen, H.S. Silva and R. Venturini de Silva, J. Non-Cryst. Sol. 271 (2000) 1.

    Google Scholar 

  15. G. Larsen, M. Buechler-Skoda, C. Nguyen, D. Vu and E. Lotero, J. Non-Cryst. Sol. 279 (2001) 161.

    Google Scholar 

  16. R. Neumann and M. Levin-Elad, J. Catal. 166 (1997) 206.

    Google Scholar 

  17. Y. Gao, R.M. Hanson, J.M. Klunder, S.Y. Ko, H. Masamune and K.B. Sharpless, J. Am. Chem. Soc. 109 (1987) 5765; J.A. Mayoral, private communication.

    Google Scholar 

  18. E. Milchert and M. Zawarski, Oxi. Commun. 22 (1999) 178.

    Google Scholar 

  19. V. Romano, A. Esposito, F. Maspero, C. Neri and M.G. Clerici, in: New Developments in Selective Oxidation, eds. G. Centi and F. Trifirò (Elsevier, Amsterdam, 1990) p. 33.

    Google Scholar 

  20. A. Corma, P. Esteve, A. Martinez and S. Valencia, J. Catal. 152 (1995) 18.

    Google Scholar 

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Karli, A., Larsen, G. A Hydrophobic Gel for Epoxidation of Olefins with Organic Peroxides. Catalysis Letters 77, 107–111 (2001). https://doi.org/10.1023/A:1012774725634

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