Skip to main content
SpringerLink
Log in

Preparation of surface-silylated and benzene-bridged Ti-containing mesoporous silica for cyclohexene epoxidation

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

Organic–inorganic hybrid Ti-containing mesostructured materials were directly synthesized from tetrabutyl titanate in acidic media by using a non-ionic surfactant P123 as a structure-directing agent, tetraethoxysilane as an inorganic silicon source and 1,4-bis-(triethoxysilyl)benzene as organicsilica. The benzene-bridged Ti-containing periodic mesoporous organosilica Ti-SBA-15-ben was further modified by surface silylation with trimethylchlorosilane. The products were characterized by various means. We find the materials maintained good mesoporous structure, their hydrophobic properties were significantly improved after silanization, and the organic silicon source in the pore walls was favorable for obtaining tetravalent active titanium ions. The catalysts were evaluated in cyclohexene epoxidation with tertbutyl hydroperoxide as an oxidant agent. With Ti-SBA-15-ben as the catalyst, the epoxide selectivity and cyclohexene conversion were improved to 59.9 and 34.7 % respectively. Moreover, surface hydrophobization by silylation treatments further increased the epoxide selectivity to 71.5 %.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. F. Hoffmann, M. Cornelius, J. Morell, M. Froba, Angew. Chem. Int. Ed. 45, 3216 (2006)

    Article  CAS  Google Scholar 

  2. R.A. Khatri, S.S.C. Chuang, Y. Soong, M. Gray, Ind. Eng. Chem. Res. 44, 3702 (2005)

    Article  CAS  Google Scholar 

  3. C.W. Jones, K. Tsuji, M.E. Davis, Nature 393, 52 (1998)

    Article  CAS  Google Scholar 

  4. C.W. Jones, K. Tsuji, M. Davis, Micropor. Mesopor. Mater. 33, 223 (1999)

    Article  CAS  Google Scholar 

  5. Q. Wei, Z. Nie, Y. Hao, Z. Chen, J. Zou, W. Wang, Mater. Lett. 56, 3611 (2005)

    Article  Google Scholar 

  6. S. Inagaki, S. Guan, Y. Fukushima, T. Ohsuna, O. Terasaki, J. Am. Chem. Soc. 121, 9611 (1999)

    Article  CAS  Google Scholar 

  7. B.J. Melde, B.T. Holland, C.F. Blandford, A. Stein, Chem. Mater. 11, 3302 (1999)

    Article  CAS  Google Scholar 

  8. T. Asefa, M.J. Mac Lachlan, N. Coombs, G.A. Ozin, Nature 402, 867 (1999)

    CAS  Google Scholar 

  9. A. Corma, U. Díaz, T. García, G. Sastre, A. Velty, J. Am. Chem. Soc. 132, 15011–15021 (2010)

    Article  CAS  Google Scholar 

  10. T. Asefa, M.J. Mac Lachlan, H. Grondey, N. Coombs, G.A. Ozin, Angew. Chem. Int. Ed. 39, 1808 (2000)

    Article  CAS  Google Scholar 

  11. C. Baleizao, B. Gigante, D. Das, M. Alvaro, H. Garcia, A. Corma, Chem. Commun. 15, 1860 (2003)

    Article  Google Scholar 

  12. S. Inagaki, S. Guan, T. Ohsuna, O. Terasaki, Nature 416, 304 (2002)

    Article  CAS  Google Scholar 

  13. C. Yoshina-Ishii, T. Asefa, N. Coombs, M.J. Mac Lachlan, G.A. Ozin, Chem. Commun. 24, 2539 (1999)

    Article  Google Scholar 

  14. M.P. Kapoor, Q. Yang, S. Inagaki, J. Am. Chem. Soc. 124, 15176 (2002)

    Article  CAS  Google Scholar 

  15. Y. Lu, H. Fan, N. Doke, D.A. Loy, R.A. Assink, D.A. La Van, C.J. Brinker, J. Am. Chem. Soc. 122, 5258 (2000)

    Article  CAS  Google Scholar 

  16. M.D. McInall, J. Scott, L. Mercier, P.J. Kooyman, Chem. Commun. 21, 2282 (2001)

    Article  Google Scholar 

  17. S. Hamoudi, S. Kaliaguine, Chem. Commun. 20, 2118 (2002)

    Article  Google Scholar 

  18. P. Yang, D. Zhao, D.I. Margolese, B.F. Chmelka, G.D. Stucky, Nature 396, 152 (1998)

    Article  CAS  Google Scholar 

  19. M.P. Kapoor, A. Bhaumik, S. Inagaki, K. Kuraoka, T. Yazawa, J. Mater. Chem. 12, 3078 (2002)

    Article  CAS  Google Scholar 

  20. W. Cho, J.W. Park, C.S. Ha, Mater. Lett. 58, 3551 (2004)

    Article  CAS  Google Scholar 

  21. M.P. Kapoor, A.K. Sinha, S. Seelan, S. Inagaki, S. Tsubota, H. Yoshida, M. Haruta, Chem. Commun. 23, 2902 (2002)

    Article  Google Scholar 

  22. X.S. Zhao, G.Q. Lu, J. Phys. Chem. B 102, 1556 (1998)

    Article  CAS  Google Scholar 

  23. A. Bhaumik, M.P. Kapoor, S. Inagaki, Chem. Commun. 4, 470 (2003)

    Article  Google Scholar 

  24. R.L. Brutchey, D.A. Ruddy, L.K. Andersen, T.D. Tilley, Langmuir 21, 9576 (2005)

    Article  CAS  Google Scholar 

  25. M.R. Prasad, M.S. Hamdy, G. Mul, E. Bouwman, E. Drent, J. Catal. 260, 288 (2008)

    Article  Google Scholar 

  26. G. Smeulders, C.J. Van Oers, K. Van Havenbergh et al., Chem. Eng. J. 175, 585–591 (2011)

    Article  CAS  Google Scholar 

  27. Sang-Soon Yoon, Won-Jin Son, Kalidas Biswas et al., Bull. Korean Chem. Soc. 29, 609–614 (2008)

    Article  CAS  Google Scholar 

  28. N.A. Melosh, P. Lipic, F.S. Bates et al., Macromolecules 32, 4332–4342 (1999)

    Article  CAS  Google Scholar 

  29. T. Blasco, M.A. Camblor, A. Corma, P. Esteve, J.M. Guil, A. Martz, J.A. Perdigo, S. Valencia, J. Phys. Chem. B 102, 75 (1998)

    Article  CAS  Google Scholar 

  30. A. Corma, M. Domine, J.A. Gaona, J.L. Jorda, M.T. Navarro, F. Rey, J. Perez-Pariente, J. Tsuji, B. Mc Culloch, L.T. Nemeth, Chem. Commun. 20, 2211 (1998)

    Article  Google Scholar 

  31. N.N. Trukhan, V.N. Romannikov, A.N. Shmakov, M.P. Vanina, E.A. Paukshtis, V.I. Bukhtiyarov, V.V. Kriventsov, I.Y. Danilov, O.A. Kholdeeva, Micropor. Mesopor. Mater. 59, 73 (2003)

    Article  CAS  Google Scholar 

  32. Y. Chen, Y. Huang, J. Xiu, X. Han, X. Bao, Appl. Catal. A Gen. 273, 185 (2004)

    Article  CAS  Google Scholar 

  33. E. Gianotti, V. Dellarocca, L. Marchese, G. Martra, S. Coluccia, T. Maschmeyer, Phys. Chem. Phys. 4, 6109 (2002)

    Article  CAS  Google Scholar 

  34. A. Modak, M. Nandi, A. Bhaumik, Catal. Today 198, 45 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the financial support from the National Natural Science Foundation of China (No. 21376200), Hunan Provincial Natural Science Foundation of China (No. 14JJ2065).

Author information

Authors and Affiliations

  1. Xiangtan University, Xiangtan, China

    Yibin Huang, Pei Yuan, Zhaowei Wu & Xia Yuan

Authors
  1. Yibin Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Pei Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhaowei Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xia Yuan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xia Yuan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, Y., Yuan, P., Wu, Z. et al. Preparation of surface-silylated and benzene-bridged Ti-containing mesoporous silica for cyclohexene epoxidation. J Porous Mater 23, 895–903 (2016). https://doi.org/10.1007/s10934-016-0146-7

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-016-0146-7

Keywords

Search

Navigation