Skip to main content
Log in

Photooxidation of cyclohexene and benzene with oxygen by fullerenes grafted on mesoporous FSM-16

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Fullerenes (C60 and C70) are grafted on mesoporous FSM-16 (pore size 2.7 nm), and the grafted fullerenes showed high activities (TON up to 3070 in 9 h) for allylic oxidation of cyclohexene with oxygen in benzene under the irradiation of UV-vis light. In these reactions, phenol is also formed by the oxidation of benzene with cyclohexene hydroperoxide produced in the allylic oxidation of cyclohexene.

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. H.W. Kroto, J.R. Heath, S.C. O'Brien, R.F. Curl and R.E. Smalley, Nature 318 (1985) 162; W. Krätschmer, L.D. Lamb, K. Fostiropoulos and D.R. Huffman, Nature 347 (1990) 354.

    Google Scholar 

  2. H. Nagashima, A. Nakaoka, Y. Saito, M. Kato, T. Kawanishi and K. Itoh, J. Chem. Soc. Chem. Commun. (1992) 377; H. Nagashima, A. Nakaoka, S. Tajima, Y. Saito and K. Itoh, Chem. Lett. (1992) 1361; N.M. Rodriges, M. Kim and R.T.K. Baker, J. Phys. Chem. 98 (1994) 13108; A. Datta, H.I. Khwaja, R.Y. Kelkar, A.R. Saple and M. Datta, J. Chem. Soc. Chem. Commun. (1996) 851; S.C. Tsang, Y.K. Chen and M.L.H. Green, Appl. Catal. B 8 (1996) 445; R. Yu, Q. Liu, K. Tan, G. Xu, S.U. Ng, H.S. Chan and T.S.A. Hor, J. Chem. Soc. Faraday Trans. 93 (1997) 2207; Y. Liu, P. Liu, Z. Zhao, S. Liu and Y. Yin, Appl. Catal. A 167 (1998) L1.

  3. A.S. Hirschon, H.-J. Wu, R.B. Wilson and R. Malhotra, J. Phys. Chem. 99 (1995) 17483.

    Google Scholar 

  4. H. Tokuyama and E. Nakamura, J. Org. Chem. 59 (1994) 1135.

    Google Scholar 

  5. M. Orfanopoulos and S. Kambourakis, Tetrahedron Lett. 35 (1994) 1945.

    Google Scholar 

  6. C.T. Kresge, M.E. Leonowicz, W.J. Roth, J.C. Vartuli and J.S. Beck, Nature 359 (1992) 710; J.S. Beck, J.C. Vartuli, W.J. Roth, M.E. Leonowicz, C.T. Kresge, K.D. Schmitt, C.T.-W. Chu, D.H. Olson, E.W. Sheppard, S.B. McCullen, J.B. Higgins and J.L. Schlenker, J. Am. Chem. Soc. 114 (1992) 10834.

    Article  Google Scholar 

  7. S. Inagaki, Y. Fukushima and K. Kuroda, J. Chem. Soc. Chem. Commun. (1993) 680; S. Inagaki, A. Koiwai, N. Suzuki, Y. Fukushima and K. Kuroda, Bull. Chem. Soc. Jpn. 69 (1996) 1449.

  8. A. Corma, Chem. Rev. 97 (1997) 2373; S. Biz and M.L. Occelli, Catal. Rev. Sci. Eng. 40 (1998) 329.

    Article  PubMed  Google Scholar 

  9. C.-Y. Chen, S.-Q. Xiao and M.E. Davis, Micropor. Mater. 4 (1993) 1.

    Google Scholar 

  10. T. Yamamoto, T. Tanaka, S. Inagaki, T. Funabiki and S. Yoshida, J. Phys. Chem. B 103 (1999) 6450.

    Google Scholar 

  11. T. Yamamoto, T. Shido, S. Inagaki, Y. Fukushima and M. Ichikawa, J. Am. Chem. Soc. 118 (1996) 5810; J. Phys. Chem. B 102 (1998) 3866; A. Fukuoka, M. Osada, T. Shido, S. Inagaki, Y. Fukushima and M. Ichikawa, Inorg. Chim. Acta 294 (1999) 281.

    Google Scholar 

  12. D.S. Shephard, T. Maschmeyer, B.F.G. Johnson, J.M. Thomas, G. Sanker, D. Ozkaya, W. Zhou, R.D. Oldroyd and R.G. Bell, Angew. Chem. Int. Ed. Eng. 36 (1997) 2242; D.S. Shephard, T. Maschmeyer, G. Sanker, J.M. Thomas, D. Ozkaya, B.F.G. Johnson, R. Raja, R.D. Oldroyd and R.G. Bell, Chem. Eur. J. 4 (1998) 1214; W. Zhou, J.M. Thomas, D.S. Shephard, B.F.G. Johnson, D. Ozkaya, T. Maschmeyer, R.G. Bell and Q. Ge, Science 280 (1998) 705.

    Google Scholar 

  13. M. Sasaki, M. Osada, N. Sugimoto, S. Inagaki, Y. Fukushima, A. Fukuoka and M. Ichikawa, Micropor. Mesopor. Mater. 21 (1998) 597; M. Sasaki, M. Osada, N. Higashimoto, T. Yamamoto, A. Fukuoka and M. Ichikawa, J. Mol. Catal. A 141 (1998) 223.

    Google Scholar 

  14. C.H. Ko and R. Ryoo, J. Chem. Soc. Chem. Commun. (1996) 2467.

  15. S. Serizawa, I. Gabrielova, T. Fujimoto, T. Shido and M. Ichikawa, J. Chem. Soc. Chem. Commun. (1994) 799.

  16. J. Tachibana, M. Chiba, T. Imamura, Y. Sasaki and M. Ichikawa, Supramol. Sci. 5 (1998) 281.

    Google Scholar 

  17. H.E.B. Lempers, J.D. Chen and R.A. Sheldon, in: Stud. Surf. Sci. Catal., Vol. 94, eds. H.K. Beyer, H.G. Karge, I. Kiricsi and J.B. Nagy (Elsevier, Amsterdam, 1995) p. 705.

    Google Scholar 

  18. E. Jorda, A. Tuel, R. Teissier and J. Kervennal, J. Catal. 175 (1998) 93.

    Google Scholar 

  19. C.C. Yang and K.C. Hwang, J. Am. Chem. Soc. 118 (1996) 4693.

    Google Scholar 

  20. S.R. Wilson, N. Kaprinidis, Y. Wu and D.I. Schuster, J. Am. Chem. Soc. 115 (1993) 8495; D.I. Schuster, J. Cao, N. Kaprinidis, Y. Wu, A.W. Jensen, Q. Lu, H. Wang and S.R. Wilson, J. Am. Chem. Soc. 118 (1996) 5639.

    Google Scholar 

  21. S. Kawata, K. Yamauchi, S. Suzuki, K. Kikuchi, H. Shiromatsu, M. Katada, K. Saito, I. Ikemoto and Y. Achiba, Chem. Lett. (1992) 1659.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fukuoka, A., Fujishima, K., Chiba, M. et al. Photooxidation of cyclohexene and benzene with oxygen by fullerenes grafted on mesoporous FSM-16. Catalysis Letters 68, 241–244 (2000). https://doi.org/10.1023/A:1019008225627

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1019008225627

Navigation