SIOC 中文
ACS
Adv search

Acta Chimica Sinica >

2012 , Vol. 70 >Issue 22: 2316 - 2322

DOI: https://doi.org/10.6023/A12070397

Article

Catalytic Hydroxylation of Benzene to Phenol with Hydrogen Peroxide over Cesium Salts of Keggin-type Heteropoly Acids

  • Feng Sujiao ,
  • Zhang Li ,
  • Ren Yuanhang ,
  • Yue Bin ,
  • Ye Lin ,
  • Wang Yu ,
  • Chen Xueying ,
  • He Heyong
Expand
  • Department of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200433

Received date: 2012-07-09

  Online published: 2012-09-23

Supported by

Project supported by the National Basic Research Program of China (No. 2009CB623506), the National Natural Science Foundation of China (No. 21173050), the Program of Shanghai Subject Chief Scientist (No. 10XD1400300) and Shanghai Leading Academic Discipline Project (B108).

Fold

Abstract

Three series of cesium salts of Keggin-type heteropoly acids (CsxH3+n-xPMo12-nVnO40, n＝0, 1, 2, x＝0.5～3.0) prepared by a solid synthesis method have been employed in the catalytic hydroxylation of benzene to phenol with H2O2. The effects of vanadium substitution number and cesium content on the catalytic activity, redox ability and hydrophobicity of the catalysts were studied. Cs2H3PMo10V2O40 exhibits high phenol yield (19.2%) and good reusability among the CsxH3+n-x- PMo12-nVnO40 catalysts.

Key words： heteropoly acid; cesium salt; benzene; hydroxylation; phenol

Cite this article

Feng Sujiao , Zhang Li , Ren Yuanhang , Yue Bin , Ye Lin , Wang Yu , Chen Xueying , He Heyong . Catalytic Hydroxylation of Benzene to Phenol with Hydrogen Peroxide over Cesium Salts of Keggin-type Heteropoly Acids[J]. Acta Chimica Sinica, 2012 , 70(22) : 2316 -2322 . DOI: 10.6023/A12070397

References

[1] Balducci, L.; Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M.; Tassinari, R.; Ungarelli, R. Angew. Chem., Int. Ed. 2003, 42, 4937.
[2] 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.
[3] 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.
[4] Liu, Y. Y.; Murata, K.; Inaba, M. Catal. Commun. 2005, 6, 679.
[5] Niwa, S.; Eswaramoorthy, M.; Nair, J.; Raj, A.; Itoh, N.; Shoji, H.; Namba, T.; Mizukami, F. Science 2002, 295, 105.
[6] Panov, G. I.; Uriarte, A. K.; Rodkin, M. A.; Sobolev, V. I. Catal. Today 1998, 41, 365.
[7] Tanarungsun, G.; Kiatkittipong, W.; Praserthdam, P.; Yamada, H.; Tagawa, T.; Assabumrungrat, S. Catal. Commun. 2008, 9, 1886.
[8] Feng, S. J.; Pei, S. P.; Yue, B.; Ye, L.; Qian, L. P.; He, H. Y. Catal. Lett. 2009, 131, 458.
[9] Feng, S. J.; Yue, B.; Wang, Y.; Ye, L.; He, H. Y. Acta Phys. Chim. Sin. 2011, 27, 2881.
[10] Benaissa, H.; Davey, P. N.; Khimyak, Y. Z.; Kozhevnikov, I. V. J. Catal. 2008, 253, 244.
[11] Chen, J. Q.; Gao, S.; Xu, J. Catal. Commun. 2008, 9, 728.
[12] Okuhara, T. Catal. Today 2002, 73, 167.
[13] Sharma, P.; Vyas, S.; Patel, A. J. Mol. Catal. A: Chem. 2004, 214, 281.
[14] Tani, M.; Sakamoto, T.; Mita, S.; Sakaguchi, S.; IshⅡ, Y. Angew. Chem., Int. Ed. 2005, 44, 2586.
[15] Dimitratos, N.; Vedrine, J. C. Appl. Catal. A: Gen. 2003, 256, 251.
[16] Leng, Y.; Wang, J.; Zhu, D. R.; Ren, X. Q.; Ge, H. Q.; Shen, L. Angew. Chem. Int. Ed. 2009, 48, 168.
[17] Kozhevnikov, I. V. Chem. Rev. 1998, 98, 171.
[18] Zhang, J.; Tang, Y.; Li, G. Y.; Hu, C. Appl. Catal. A: Gen. 2005, 278, 251.
[19] Rao, K. T. V.; Rao, P. S. N.; Nagaraju, R.; Prasad, P. S. S.; Lingaiah, N. J. Mol. Catal. A: Chem. 2009, 303, 84.
[20] Narasimharao, K.; Brown, D. R.; Lee, A. F.; Newman, A. D.; Siril, P. F.; Tavener, S. J.; Wilson, K. J. Catal. 2007, 248, 226.
[21] Okuhara, T.; Mizuno, N.; Misono, M. Appl. Catal. A: Gen. 2001, 222, 63.
[22] Kimura, M.; Nakato, T.; Okuhara, T. Appl. Catal. A: Gen. 1997, 165, 227.
[23] Dimitratos, N.; Vedrine, J. C. Catal. Today 2003, 81, 561.
[24] Knapp, C.; Ui, T.; Nagai, K.; Mizuno, N. Catal. Today 2001, 71, 111.
[25] Marchal-Roch, C.; Laronze, N.; Guillou, N.; Teze, A.; Herve, G. Appl. Catal. A: Gen. 2000, 199, 33.
[26] Kuznetsova, L. I.; Detusheva, L. G.; Kuznetsova, N. I.; Koshcheev, S. V.; ZaikovskⅡ, V. I.; Chesalov, Y. A.; Rogov, V. A.; Fenelonov, V. B.; Likholobov, V. A. Kinet. Catal. 2009, 50, 205.
[27] Villabrille, P.; Romanelli, G.; Vazquez, P.; Caceres, C. Appl. Catal. A: Gen. 2004, 270, 101.
[28] Yamaguchi, S.; Sumimoto, S.; Ichihashi, Y.; Nishiyama, S.; Tsuruya, S. Ind. Eng. Chem. Res. 2005, 44, 1.
[29] Guo, X. J.; Huang, C. P.; Li, Y. X. Korean J. Chem. Eng. 2008, 25, 697.
[30] Matachowski, L.; Zieba, A.; Zembala, M.; Drelinkiewicz, A. Catal. Lett. 2009, 133, 49.
[31] Wang, R.; Yu, F. L.; Zhang, G. F.; Zhao, H. X. Catal. Today 2010, 150, 37.
[32] Na, K.; Okuhara, T.; Misono, M. Chem. Lett. 1993, 1141.
[33] Tatematsu, S.; Hibi, T.; Okuhara, T.; Misono, M. Chem. Lett. 1984, 865.
[34] Zou, Y.; Yue, B.; Zhang, B.; He, H. Y. Chem. Lett. 2006, 35, 202.
[35] Zhou, Y.; Yue, B.; Bao, R. L.; Liu, S. X.; He, H. Y. Chin. J. Chem. 2006, 24, 1001.
[36] Tsigdinos, G. A.; Hallada, C. J. Inorg. Chem. 1968, 7, 437.
[37] Okuhara, T.; Mizuno, N.; Misono, M. In Advances in Catalysis, Vol. 41, Eds.: Eley, D. D.; Haag, W. O.; Gates, B., Academic Press Inc, San Diego, 1996, pp. 113—252.
[38] Rocchicciolideltcheff, C.; Fournier, M. J. Chem. Soc. 1991, 87, 3913.
[39] Lee, J. K.; Melsheimer, J.; Berndt, S.; Mestl, G.; Schlogl, R.; Kohler, K. Appl. Catal. A: Gen. 2001, 214, 125.
[40] Essayem, N.; Holmqvist, A.; Gayraud, P. Y.; Vedrine, J. C.; Ben Taarit, Y. J. Catal. 2001, 197, 273.
[41] Berndt, S.; Herein, D.; Zemlin, F.; Beckmann, E.; Weinberg, G.; Schutze, J.; Mestl, G.; Schlogl, R. Phys. Chem. Chem. Phys. 1998, 102, 763.
[42] Langpape, M.; Millet, J. M. M.; Ozkan, U. S.; Boudeulle, M. J. Catal. 1999, 181, 80.
[43] Dai, L. M.; You, W. S.; Li, Y. G.; Wang, E. B.; Qi, L. J.; Tang, J.; Bai, X. L. Inorg. Chem. Commun. 2010, 13, 421.
[44] Sadakane, M.; Steckhan, E. Chem. Rev. 1998, 98, 219.
[45] Sha, J.; Peng, J.; Liu, H.; Chen, J.; Dong, B.; Tian, A.; Su, Z. Eur. J. Inorg. Chem. 2007, 1268.
[46] Villabrille, P.; Romanelli, G.; Gassa, L.; Vazquez, P.; Caceres, C. Appl. Catal. A: Gen. 2007, 324, 69.
[47] Song, I. K.; Barteau, M. A. J. Mol. Catal. A: Chem. 2004, 212, 229.
[48] Ai, M. Appl. Catal. 1982, 4, 245.
[49] Li, X. K.; Zhao, J.; Ji, W. J.; Zhang, Z. B.; Chen, Y.; Au, C. T.; Han, S.; Hibst, H. J. Catal. 2006, 237, 58.
[50] Mestl, G.; Ilkenhans, T.; Spielbauer, D.; Dieterle, M.; Timpe, O.; Krohnert, J.; Jentoft, F.; Knozinger, H.; Schlogl, R. Appl. Catal. A: Gen. 2001, 210, 13.
[51] Okuhara, T. Chem. Rev. 2002, 102, 3641.
[52] Ilkenhans, T.; Herzog, B.; Braun, T.; Schlogl, R. J. Catal. 1995, 153, 275.
[53] Lemke, K.; Ehrich, H.; Lohse, U.; Berndt, H.; Jahnisch, K. Appl. Catal. A: Gen. 2003, 243, 41.
[54] Chen, J. Q.; Gao, S.; Xu, J. Catal. Commun. 2008, 9, 728.
[55] Kharat, A. N.; Moosavikia, S.; Jahromi, B. T.; Badiei, A. J. Mol. Catal. A: Chem. 2011, 348, 14.
[56] Song, S. Q.; Yang, H. X.; Rao, R. C.; Liu, H. D.; Zhang, A. M. Appl. Catal. A: Gen. 2010, 375, 265.
[57] Zhu, Y. J.; Dong, Y. L.; Zhao, L. N.; Yuan, F. L. J. Mol. Catal. A: Chem. 2010, 315, 205.
[58] Joseph, J. K.; Singhal, S.; Jain, S. L.; Sivakumaran, R.; Kumar, B.; Sain, B. Catal. Today 2009, 141, 211.
Options
Outlines

/

〈 〉