Citation: FENG Su-Jiao, YUE Bin, WANG Yu, YE Lin, HE He-Yong. Hydroxylation of Benzene over V-HMS Catalysts with the Addition of Fe as the Second Metal Component[J]. Acta Physico-Chimica Sinica, ;2011, 27(12): 2881-2886. doi: 10.3866/PKU.WHXB20112881 shu

Hydroxylation of Benzene over V-HMS Catalysts with the Addition of Fe as the Second Metal Component

1.
Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University,Shanghai 200433, P. R. China

Received Date: 15 July 2011
Available Online: 26 September 2011
Fund Project: 国家重点基础研究发展规划项目(973) (2009CB623506) (973) (2009CB623506) 国家高技术研究发展计划(863) (2009AA033701) (863) (2009AA033701) 上海市优秀学科带头人计划(10XD1400300) (10XD1400300)上海市重点学科建设项目(B108)资助 (B108)

Second metals (Fe, Al, Cu, Ni, Co, Mo, Cr) were incorporated into V-HMS catalyst by impregnation to enhance the catalytic activity for the hydroxylation of benzene with hydrogen peroxide as the oxidant. Among the studied second metals, Fe was found to be effective in improving the catalytic performance. Therefore, we synthesized a series of Fe_xV_y-HMS catalysts containing different amounts of Fe and V by the co-synthesis method. The catalysts were characterized by powder X-ray diffraction (XRD), N₂ physisorption, transmission electron microscopy (TEM), NH₃ temperature-programmed desorption (NH₃- TPD), and H₂ temperature-programmed reduction (H₂-TPR). The characterization results show that the mesoporous structure of HMS is maintained and the addition of Fe creates new acid sites and a stronger redox ability. Catalytic tests show that vanadium species are the active species and that the iron species promote the reaction. Under optimal reaction conditions, the Fe_0.04V_0.06-HMS catalyst gives the best catalytic performance with a highest phenol yield of 18.1% by comparison with 13.1% over the Fe-free catalyst Fe_0.00V_0.06-HMS. We propose a possible mechanism involving the Fe and V species for the hydroxylation of benzene with H₂O₂ as the oxidant.
- Iron,
- Vanadium,
- Mesoporous silica,
- Benzene,
- Hydroxylation,
- Phenol
1. [1]
  (1) Niwa, S.; Eswaramoorthy, M.; Nair, J.; Raj, A.; Itoh, N.; Shoji, H.; Namba, T.; Mizukami, F. Science 2002, 295, 105.
2. [2]
  (2) Li, Y.; Xia, H. A.; Fan, F. T.; Feng, Z. C.; van Santen, R. A.; Hensen, E. J. M.; Li, C. Chem. Commun. 2008, No. 6, 774.
3. [3]
  (3) Balducci, L.; Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M.; Tassinari, R.; Ungarelli, R. Angew. Chem. Int. Edit. 2003, 42, 4937.
4. [4]
  (4) Bhaumik, A.; Mukherjee, P.; Kumar, R. J. Catal. 1998, 178, 101.
5. [5]
  (5) Choi, J. S.; Kim, T. H.; Choo, K. Y.; Sung, J. S.; Saidutta, M. B.; Ryu, S. O.; Song, S. D.; Ramachandra, B.; Rhee, Y.W. Appl. Catal. A-Gen. 2005, 290, 1.
6. [6]
  (6) Monfared, H. H.; Amouei, Z. J. Mol. Catal. A-Chem. 2004, 217, 161.
7. [7]
  (7) Tanarungsun, G.; Kiatkittipong,W.; Praserthdam, P.; Yamada, H.; Tagawa, T.; Assabumrungrat, S. Catal. Commun. 2008, 9, 1886.
8. [8]
  (8) Tani, M.; Sakamoto, T.; Mita, S.; Sakaguchi, S.; Ishii, Y. Angew. Chem. Int. Edit. 2005, 44, 2586.
9. [9]
  (9) Barbera, D.; Cavani, F.; D'Alessandro, T.; Fornasari, G.; Guidetti, S.; Aloise, A.; Giordano, G.; Piumetti, M.; Bonelli, B.; Zanzottera, C. J. Catal. 2010, 275, 158.
10. [10]
  (10) Kubacka, A.;Wang, Z. L.; Sulikowski, B.; Corberan, V. C. J. Catal. 2007, 250, 184.
11. [11]
  (11) Bal, R.; Tada, M.; Sasaki, T.; Iwasawa, Y. Angew. Chem. Int. Edit. 2006, 45, 448.
12. [12]
  (12) Ribera, A.; Arends, I.W. C. E.; de Vries, S.; Perez-Ramirez, J.; Sheldon, R. A. J. Catal. 2000, 195, 287.
13. [13]
  (13) Panov, G. I.; Uriarte, A. K.; Rodkin, M. A.; Sobolev, V. I. Catal. Today 1998, 41, 365.
14. [14]
  (14) Joseph, J. K.; Singhal, S.; Jain, S. L.; Sivakumaran, R.; Kumar, B.; Sain, B. Catal. Today 2009, 141, 211.
15. [15]
  (15) Renuka, N. K. J. Mol. Catal. A-Chem. 2010, 316, 126.
16. [16]
  (16) Miyahara, T.; Kanzaki, H.; Hamada, R.; Kuroiwa, S.; Nishiyama, S.; Tsuruya, S. J. Mol. Catal. A-Chem. 2001, 176, 141.
17. [17]
  (17) Panov, G. I.; Kharitonov, A. S.; Sobolev, V. I. Appl. Catal. A-Gen. 1993, 98, 1.
18. [18]
  (18) Neidig, M. L.; Hirsekorn, K. F. Catal. Commun. 2011, 12, 480.
19. [19]
  (19) Tanev, P. T.; Chibwe, M.; Pinnavaia, T. J. Nature 1994, 368, 321.
20. [20]
  (20) Williams, T.; Beltramini, J.; Lu, G. Q. Microporous Mesoporous Mat. 2006, 88, 91.
21. [21]
  (21) Zhang,W. Z.;Wang, J. L.; Tanev, P. T.; Pinnavaia, T. J. Chem. Commun. 1996, No. 8, 979.
22. [22]
  (22) George, J.; Shylesh, S.; Singh, A. P. Appl. Catal. A-Gen. 2005, 290, 148.
23. [23]
  (23) Shiraishi, Y.; Morishita, M.; Teshima, Y.; Hirai, T. J. Phys. Chem. B 2006, 110, 6587.
24. [24]
  (24) Zhu, Y. J.; Dong, Y. L.; Zhao, L. N.; Yuan, F. L. J. Mol. Catal. A-Chem. 2010, 315, 205.
25. [25]
  (25) Liu, Y. Y.; Murata, K.; Inaba, M.; Mimura, N. Catal. Lett. 2003, 89, 49.
26. [26]
  (26) Knotek, P.; Capek, L.; Bulanek, R.; Adam, J. Top. Catal. 2007, 45, 51.
27. [27]
  (27) Parvulescu, V.; Tablet, C.; Anastasescu, C.; Su, B. L. Catal. Today 2004, 93-5, 307.
28. [28]
  (28) Parvulescu, V.; Anastasescu, C.; Su, B. L. J. Mol. Catal. AChem. 2004, 211, 143.
29. [29]
  (29) Gutierrez, O. Y.; Fuentes, G. A.; Salcedo, C.; Klimova, T. Catal. Today 2006, 116, 485.
30. [30]
  (30) Zhang, Y. H.; Gao, F.;Wan, H. Q.;Wu, C.; Kong, Y.;Wu, X. C.; Zhao, B.; Dong, L.; Chen, Y. Microporous Mesoporous Mat. 2008, 113, 393.
31. [31]
  (31) Kong, Y.; Xu, X. J.;Wu, Y.; Zhang, R.;Wang, J. Chin. J. Catal. 2008, 29, 385. [孔岩, 徐鑫杰, 吴勇, 张瑞, 王军. 催化学报, 2008, 29, 385.]
32. [32]
  (32) Tanarungsun, G.; Kiatkittipong,W.; Praserthdam, P.; Yamada, H.; Tagawa, T.; Assabumrungrat, S. J. Ind. Eng. Chem. 2008, 14, 596.
33. [33]
  (33) Gu, Y. Y.; Li, J.; Zhao, X. H.;Wang, L. P.; Shan, Y. K. Acta Chim. Sin. 2007, 65, 2423. [顾颖颖, 李疆, 赵新华, 王莉萍, 单永奎. 化学学报, 2007, 65, 2423.]
34. [34]
  (34) Feng, S. J.; Pei, S. P.; Yue, B.; Ye, L.; Qian, L. P.; He, H. Y. Catal. Lett. 2009, 131, 458.
35. [35]
  (35) Fornes, V.; Lopez, C.; Lopez, H. H.; Martinez, A. Appl. Catal. A-Gen. 2003, 249, 345.
36. [36]
  (36) Braganca, L. F. F. P. G.; Avilez, R. R.; de Silva, M. I. Colloid Surface A 2010, 358, 79.
37. [37]
  (37) Lemke, K.; Ehrich, H.; Lohse, U.; Berndt, H.; Jahnisch, K. Appl. Catal. A-Gen. 2003, 243, 41.
38. [38]
  (38) Arichi, J.; Eternot, M.; Louis, B. Catal. Today 2008, 138, 117.
39. [39]
  (39) Seo, Y. J.; Mukai, Y.; Tagawa, T.; to, S. J. Mol. Catal. A-Chem. 1997, 120, 149.
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