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Catalytic Oxidation of Cyclohexene with Hydrogen Peroxide over Cu(II)-Cyclam-SBA-16 Catalyst

  • Prasetyanto, Eko Adi (Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University) ;
  • Park, Sang-Eon (Laboratory of Nano-Green Catalysis and Nano Center for Fine Chemicals Fusion Technology, Department of Chemistry, Inha University)
  • Published : 2008.05.20

Abstract

A copper cyclam-type complex was successfully immobilized onto mesoporous silica SBA-16. Characterization by NIR spectroscopy and TGA analysis confirmed that copper cyclam complex is immobilized onto mesoporous SBA-16. The Cu(II)-Cyclam-SBA-16 was proven to be a good catalyst for oxidation reaction of cyclohexene with conversion up to 77.8% after 13 h reaction and providing a high selectivity to cyclohexenol and 3-hydroperoxycyclohex-1-ene. The results suggest that the copper species play a major role as catalyst via reversible redox cycles as proven by cyclic voltammetry analysis.

Keywords

References

  1. Medina, J. C.; Gabriunas, N.; Paez-Mozo, E. J. Mol. Catal. A: Chem. 1997, 115, 233 https://doi.org/10.1016/S1381-1169(96)00340-8
  2. Jin, C.; Fan, W.; Jia, Y.; Fan, B.; Ma, J.; Li, R. J. Mol. Catal. A: Chem. 2006, 249, 23 https://doi.org/10.1016/j.molcata.2005.12.035
  3. Serwicka, E. M.; Poltowicz, J.; Bahranowski, K.; Olejniczak, Z.; Jones, W. Applied Catalysis A: General 2004, 275, 9 https://doi.org/10.1016/j.apcata.2004.07.005
  4. Ayala, V.; Corma, A.; Iglesias, M.; Sanchez, F. J. Mol. Catal. A: Chem. 2004, 221, 201
  5. Silva, A. R.; Freire, C.; de Castro, B.; Freitas, M. M. A.; Figueiredo, J. L. Microporous Mesoporous Mater. 2001, 46, 211 https://doi.org/10.1016/S1387-1811(01)00297-9
  6. Silva, A. R.; Freitas, M. M. A.; Freire, C.; de Castro, B.; Figueiredo, J. L. Langmuir 2002, 18, 8017 https://doi.org/10.1021/la025833c
  7. Sujandi; Prasetyanto, E. A.; Han, S.-C.; Park, S.-E. Bull. Korean Chem. Soc. 2006, 27, 1381 https://doi.org/10.5012/bkcs.2006.27.9.1381
  8. Zhao, D.; Feng, J.; Huo, Q.; Melosh, N.; Fredrickson, G. H.; Chmelka, B. F.; Stucky, G. D. Science 1998, 279, 548 https://doi.org/10.1126/science.279.5350.548
  9. Sakamoto, Y.; Kaneda, M.; Terasaki, O.; Zhao, D. Y.; Kim, J. M.; Stucky, G.; Shin, H. J.; Ryoo, R. Nature 2000, 408, 449 https://doi.org/10.1038/35044040
  10. Hwang, Y. K.; Chang, J.-S.; Kwon, Y.-U.; Park, S.-E. Microporous Mesoporous Mater. 2004, 68, 21 https://doi.org/10.1016/j.micromeso.2003.12.004
  11. Alvarez, L. X.; Christ, M. L.; Sorokin, A. B. Applied Catalysis A:General 2007, 325, 303 https://doi.org/10.1016/j.apcata.2007.02.045
  12. Bandini, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A.; Ventrici, C. Chem. Commun. 2007, 616
  13. Velusamy, S.; Punniyamurthy, T. Tetrahedron Lett. 2003, 44, 8955 https://doi.org/10.1016/j.tetlet.2003.10.016
  14. Wolfgang, K. Angew. Chem. Int. Ed. 2003, 42, 1088 https://doi.org/10.1002/anie.200390290
  15. Lindoy, L. F. The Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press: Cambridge, 1989
  16. Harrowfield, J. M.; Kim, Y.; Koutsantonis, G. A.; Lee, Y. H.; Thuery, P. Inorg. Chem. 2004, 43, 1689 https://doi.org/10.1021/ic034912o
  17. Arakawa, H.; Aresta, M.; Armor, J.; Barteau, M.; Beckman, E.; Bell, A.; Bercaw, J.; Creutz, C.; Dixon, D. A.; Dixon, D.; Domen, K.; DuBois, D.; Eckert, J.; Fujita, E.; Gibson, D.; Goddard, W.; Goodman, D.; Keller, J.; Kubas, G.; Kung, H.; Lyons, J.; Manzer, L.; Marks, T.; Morokuma, K.; Nicholas, K.; Periana, R.; Que, L.; Rostrup-Nielson, J.; Sachtler, W.; Schmidt, L.; Sen, A.; Somorjai, G.; Stair, P.; Stults, B.; Tumas, W. Chem. Rev. 2001, 101, 953 https://doi.org/10.1021/cr000018s
  18. Sujandi; Han, S.-C.; Han, D.-S.; Jin, M.-J.; Park, S.-E. J. Catal. 2006, 243, 410 https://doi.org/10.1016/j.jcat.2006.08.010
  19. Prasetyanto, E. A.; Sujandi; Lee, S.-C.; Park, S.-E. Bull. Korean Chem. Soc. 2007, 28, 2359 https://doi.org/10.5012/bkcs.2007.28.12.2359
  20. Hwang, Y.-K.; Chang, J.-S.; Park, S.-E.; Kim, D.-S.; Kwon, Y.-U.; Jhung, S.-H.; Hwang, J.-S.; Park, M.-S. Angew. Chem. Int. Ed. 2005, 44, 556 https://doi.org/10.1002/anie.200461403
  21. Sujandi; Park, S.-E.; Han, D.-S.; Han, S.-C.; Jin, M.-J.; Ohsuna, T. Chem. Commun. 2006, 4131
  22. Takeuchi, M.; Martra, G.; Coluccia, S.; Anpo, M. J. Phys. Chem. B 2005, 109, 7387 https://doi.org/10.1021/jp040630d
  23. Xu, L.; Fu, J. H.; Schlup, J. R. J. Am. Chem. Soc. 1994, 116, 2821 https://doi.org/10.1021/ja00086a015
  24. Lever, A. B. P. Inorganic Electronic Spectroscopy, 2nd ed.; Elsevier: New York, 1984
  25. Koola, J. D.; Kochi, J. K. J. Org. Chem. 1987, 52, 4545 https://doi.org/10.1021/jo00229a022
  26. Ji, D.; Zhao, R.; Lv, G.; Qian, G.; Yan, L.; Suo, J. Applied Catalysis A: General 2005, 281, 39 https://doi.org/10.1016/j.apcata.2004.11.010

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