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.
1. [1]
  Xuefei Zhao , Xuhong Hu , Zhenhua Jia . 理论与计算化学在傅-克烷基化反应教学中的应用. University Chemistry, 2025, 40(8): 360-367. doi: 10.12461/PKU.DXHX202410008
2. [2]
  Mengfan Gong , Dongju Zhang . Estimating Delocalization Energies of 1,3-Butadiene and Benzene with Isodesmic Reactions: A Relatively Precise Approach. University Chemistry, 2026, 41(4): 457-463. doi: 10.12461/PKU.DXHX202505036
3. [3]
  Wenke ZHENG , Ce LIU , Wei CHEN , Hongshan KE , Fanlong ZENG , Yibo LEI , Anyang LI , Wenyuan WANG . Synthesis and bonding analysis of low-coordinate Fe and Cr complexes with ultra-bulky silylamino groups. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1285-1293. doi: 10.11862/CJIC.20250095
4. [4]
  Jingyu Cai , Xiaoyu Miao , Yulai Zhao , Longqiang Xiao . Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol. University Chemistry, 2024, 39(4): 169-177. doi: 10.3866/PKU.DXHX202311028
5. [5]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
6. [6]
  Jiaxi Xu , Yuan Ma . Stable Conformation of Several Common Aromatic Compounds. University Chemistry, 2025, 40(12): 183-186. doi: 10.12461/PKU.DXHX202508007
7. [7]
  Di ZHANG , Tianxiang XIE , Xu HE , Wanyu WEI , Qi FAN , Jie QIAO , Gang JIN , Ningbo LI . Construction and antitumor activity of pH/GSH dual-responsive magnetic nanodrug. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 786-796. doi: 10.11862/CJIC.20240329
8. [8]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144
9. [9]
  Bowen Liu , Jianjun Zhang , Han Li , Bei Cheng , Chuanbiao Bie . MOF-derived ZnO/PANI S-scheme heterojunction for efficient photocatalytic phenol mineralization coupled with H₂O₂ generation. Acta Physico-Chimica Sinica, 2025, 41(10): 100121-0. doi: 10.1016/j.actphy.2025.100121
10. [10]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182
11. [11]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
12. [12]
  Bo YAN , Wenjuan JI , Lu XU , Wenzhuang LEI , Haiying YANG , Yunlong FU . Highly sensitive electrochemical detection for 4-aminophenol based on pore-confined nitrogen-rich tetranuclear cobalt-oxo cluster metal-organic framework. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1175-1189. doi: 10.11862/CJIC.20250375
13. [13]
  Sihan Wang , Chenxi Yu , Shuzhang Ran , Jiawei Chen , Shoutong Rao , Xinyi Liang , Ruiqi Dong , Guixiang Zeng , Guoqiang Wang , Jing Ma . 铁配合物合成与性质探究的数智化改进——大学化学实验中“磺基水杨酸合铁配合物的组成与稳定常数的测定”的创新设计. University Chemistry, 2026, 41(5): 36-49. doi: 10.12461/PKU.DXHX202511137
14. [14]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027
15. [15]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
16. [16]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
17. [17]
  Xinyi MA , Yuhang XIAO , Qian LI , Zihuan YAN , Chengyan LIU , Xiguang GAO , Hongju YIN , Feixiang CHENG . Thienyl metal coordination polymers: Preparation and photocatalytic degradation performance of phenol. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 969-979. doi: 10.11862/CJIC.20250317
18. [18]
  Meiran Li , Yingjie Song , Xin Wan , Yang Li , Yiqi Luo , Yeheng He , Bowen Xia , Hua Zhou , Mingfei Shao . Nickel-Vanadium Layered Double Hydroxides for Efficient and Scalable Electrooxidation of 5-Hydroxymethylfurfural Coupled with Hydrogen Generation. Acta Physico-Chimica Sinica, 2024, 40(9): 2306007-0. doi: 10.3866/PKU.WHXB202306007
19. [19]
  Weifeng HUANG , Jingteng FENG , Xin WANG , Zhilong XU , Jiaxin LI , Guanghui SUN , Yan SUN , Yao SUN , Xi LIU , Yinfeng CHENG , Guangri XU , Li YANG . In-situ self-assembly of hydrated vanadium pentoxide on Zn foil for stable Zn anodes. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 562-570. doi: 10.11862/CJIC.20250267
20. [20]
  Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO₂ mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398

Get Citation

PDF

XML

Metrics

PDF Downloads(868)
Abstract views(3959)
HTML views(44)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142