Zinc powder as an effective reducing reagent during liquid-phase oxidation of benzene to phenol using molecular oxygen over V-substituted heteropoly acid catalysts

Industrial and Engineering Chemistry Research

Volumn 45, Issue 22, 2006, Pages 7444-7450

  Sumimoto, Shingo ^a   Tanaka, Chiaki ^a   Yamaguchi, Sho Ta ^a   Ichihashi, Yuichi ^a   Nishiyama, Satoru ^a   Tsuruya, Shigeru ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; OXYGEN; PHENOLS; POWDER METALS; REACTION KINETICS; SUBSTITUTION REACTIONS; ZINC;

GASEOUS OXYGEN; HETEROPOLYACID CATALYST; MOLECULAR OXYGEN;

BENZENE;

BENZENE; CATALYSTS; OXYGEN; PHENOLS; POWDER METALS; REACTION KINETICS; SUBSTITUTION REACTIONS; ZINC;

EID: 33751271182     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie060743e     Document Type: Article

References (39)

1. Miyake, T. Phenol Synthesis by Direct Oxidation of Benzene (in Japanese). PETROTECH 1995, 18, 840.
2. Devos, D. D.; Sels, B. F.; Jacobs, P. A. Immobilization of Homogeneous Oxidation Catalysts. Adv. Catal. 2001, 46, 1.
3. Dixon, W. T.; Norman R. O. C. An Intermediate in Homolytic Aromatic Substitution. Pro. Chem. Soc. 1963, 97.
4. Kuznetsova, L. I.; Detusheva, L. G.; Fedotov, M. A.; Likholobov, V. A. Catalytic Properties of Heteropoly Complexes Containing Fe(III) Ions in Benzene Oxidation by Hydrogen Peroxide. J. Mol. Catal. A: Chem. 1996, 111, 81.
5. Nomiya, K.; Yanagibayashi, H.; Nozaki, C.; Kondoh K.; Hiramatsu E.; Shimizu Y. Hydroxylation of Benzene Catalyzed by Selectively Site-Substituted Vanadium (V) Heteropolytungstates in the Presence of Hydrogen Peroxide. J. Mol. Catal. A: Chem. 1996, 114, 181.
6. Bhaumik, A.; Mukherjee, P.; Kumar, R. Triphase Catalysis over Titanium-Silicate Molecular Sieves under Solvent-Free Conditions 1. Direct Hydroxylation of Benzene. J. Catal. 1998, 178, 101.
7. Stockmann, M.; Konietzni, F.; Notheis, J. U.; Voss, J.; Keune, W.; Maier, W. F. Selective Oxidation of Benzene to Phenol in the Liquid Phase with Amorphous Microporous Mixed Oxides. Appl. Catal., A 2001, 208, 343.
8. Balducci, L.; Bianchi, D.; Bortolo, R.; D'Aloisio, R.; Ricci, M.; Tassinari, R.; Ungarelli, R. Direct Oxidation of Benzene to Phenol with Hydrogen Peroxide over a Modified Titanium Silicate. Angew. Chem., Int. Ed. 2003, 42, 4937.
9. Sasaki, K.; Ito, S.; Saheki, Y.; Kinoshita, T.; Yamasaki, T.; Harada, J. One-Step Oxidation of Benzene to Phenol under Ambient Conditions. Chem. Lett. 1983, 37.
10. Kunai, A.; Hata, S.; Ito, S.; Sasaki, K. Mechanistic Study of Air Oxidation of Benzene in Sulfuric Acid Catalyzed by Cuprous Ions. J. Org. Chem. 1986, 51, 3471.
11. Ito, S.; Kunai, A.; Okada, H.; Sasaki, K. Direct Conversion of Benzene to Hydroquinone. Cooperative Action of Cu(I) Ion and Dioxygen. J. Org. Chem. 1988, 53, 296.
12. Ito, S.; Yamasaki, T.; Okada, H.; Okino, S.; Sasaki, K. Oxidation of Benzene to Phenols with Molecular Oxygen by Copper (I) Chloride. J. Chem. Soc., Perkin Trans. 2 1988, 285.
13. Passoni, L. C.; Cruz, A. T.; Buffon, R.; Schuchardt U. Direct Selective Oxidation of Benzene to Phenol Using Molecular Oxygen in the Presence of Palladium and Heteropolyacids. J. Mol. Catal. A: Chem. 1997, 120, 117.
14. 40 and Palladium Acetate in VPI-5 and MCM-41 and Their Use in the Catalytic Oxidation of Benzene to Phenol. J. Mol. Catal., A: Chem. 1998, 134, 229.
15. Kitano, T.; Wani, T.; Ohnishi, T.; Li-Fen, J.; Kuroda, Y.; Kunai, A.; Sasaki, K. Gas Phase Oxidation of Benzene to Phenol Using Pd-Cu Composite Catalysts. Effect of Temperature, Feeding Gas and Catalyst Composition. Catal. Lett. 1991, 11, 11.
16. Kitano, T.; Nakai, T.; Nitta, M.; Mori, M.; Ito, S.; Sasaki, K. Gas Phase Oxidation of Benzene to Phenol under the Simultaneous Feeding of Hydrogen and Oxygen. III. Catalyst Prepared from Cu(II) Phosphate. Bull. Chem. Soc. Jpn. 1994, 67, 2850.
17. Miyake, T.; Hamada, M.; Niwa, H.; Nishizaka, M.; Oguri, M. Effect of Vanadium Compound on the Synthesis of Phenol by Hydroxylation of Benzene with Oxygen and Hydrogen on Platinum Catalyst. J. Mol Catal. A: Chem. 2002, 178, 199.
18. Itoh, N.; Niwa, S.; Mizukami, F.; Inoue, T.; Igarashi, A.; Namba, T. Catalytic Palladium Membrane for Reductive Oxidation of Benzene to Phenol. Catal. Commun. 2003, 4, 243.
19. Battistel. E: Tassinari, R.; Fornaroli, M.; Bonoldi, L. Oxidation of Benzene by Molecular Oxygen Catalyzed by Vanadium. J. Mol. Catal. A: Chem. 2003, 202, 107.
20. Tani, M.; Sakamoto, T.; Mita, S.; Sakaguchi, S.; Ishii, Y. Hydroxylation of Benzene to Phenol under Air and Carbon Monoxide Catalyzed by Molybdovanadophosphoric Acid. Angw. Chem., Int. Ed. 2005, 44, 2586.
21. Yamanaka, H.; Hamada, R.; Nibuta, H.; Nishiyama, S.; Tsuruya, S. Gas-Phase Catalytic Oxidation of Benzene over Cu-Supported ZSM-5 Catalysts: An Attempt of One-Step Production of Phenol. J. Mol. Catal. A: Chem. 2002, 178, 89.
22. Hamada, R.; Shibata, Y.; Nishiyama, S.; Tsuruya, S. One-Step Gas-Phase Catalytic Oxidation of Benzene to Phenol with Molecular Oxygen over Cu-Supported ZSM-5 Zeolites. Phys. Chem. Chem. Phys. 2003, 5, 956.
23. Shibata, Y.; Hamada, R.; Ueda, T.; Ichihashi, Y.; Nishiyama, S.; Tsuruya, S. Gas-Phase Catalytic Oxidation of Benzene to Phenol over Cu-Impregnated HZSM-5 Catalysts. Ind. Eng. Chem. Res. 2005, 44, 8765.
24. Ohtani, T.; Nishiyama, S.; Tsuruya, S.; Masai. M. In Liquid-Phase Oxidation of Benzene with Molecular Oxygen Catalyzed by Cu-Zeolites; Guczi, L., Solymosi, F., Tetenyi, P., Eds.; Proceedings of 10th International Congress on Catalysis, Budapest; Elsevier: Amsterdam, 1993; p 1999.
25. Ohtani, T.; Nishiyama, S.; Tsuruya, S.; Masai, S. Liquid-Phase Benzene Oxidation to Phenol with Molecular Oxygen Catalyzed by Cu-Zeolites. J. Catal. 1995, 155, 158.
26. Okamura, J.; Nishiyama, S.; Tsuruya, S.; Masai, S. Formation of Cu-Supported Mesoporous Silicates and Aluminosilicates and Liquid-Phase Oxidation of Benzene Catalyzed by the Cu-Mesoporous Silicates and Aluminosilicates. J. Mol. Catal. A: Chem. 1998, 135, 133.
27. 3 Catalysts Prepared by Co-Precipitation Method. J. Mol. Catal. A: Chem. 2001, 176, 141.
28. 3 in the Liquid-Phase Oxidation of Benzene in Aqueous Solvent with High Acetic Acid Concentration. J. Mol. Catal. A: Chem. 2004, 208, 203.
29. Kitamura, T.; Kanzaki, H.; Hamada, R.; Nishiyama, S.; Tsuruya, S. Liquid-Phase Oxidation of Benzene to Phenol by Copper Catalysts in Aqueous Solvent with a High Acetic Acid Concentration. Can. J. Chem. 2004, 82, 1597.
30. Ishida, M.; Masumoto, Y.; Hamada, R.; Nishiyama, S.; Tsuruya, S.; Masai, M. Liquid-Phase Oxygenation of Benzene over Supported Vanadium Catalysts. J. Chem. Soc., Perkin Trans. 2 1999, 847.
31. Masumoto, Y.; Hamada, R.; Yokota, K.; Nishiyama, S.; Tsuruya, S. Liquid-Phase Oxidation of Benzene to Phenol by Vanadium Catalysts in Aqueous Solvent with High Acetic Acid Concentration. J. Mol. Catal. A: Chem. 2002, 184, 215.
32. Yamaguchi, S.; Sumimoto, S.; Ichihashi, Y.; Nishiyama, S.; Tsuruya, S. Liquid-Phase Oxidation of Benzene over V-Substituted Heteropolyacid Catalysts. Ind. Eng. Chem. Res. 2004, 44, 1.
33. Tsigdions G. A.; Hallada C. J. Molybdovanadophosphoric Acids and Their Salts. I. Investigation of Methods of Preparation and Characterization. Inorg. Chem. 1968, 7, 437.
34. Bardin B. B.; Davis R. J. Characterization of Copper and Vanadium Containing Heteropolyacid Catalysts for Oxidative Dehydrogenation of Propane. Appl. Catal, A 1999, 185, 283.
35. Izumi A.; Oohtake M. Shokubai Sekkei (Catalysts Design). Kagaku Sosetsu (edited by Chem. Soc. Jpn.) 1982, 41, 116.
36. Bardin B. B.; Davis R. J. Characterization of Copper and Vanadium Containing Heteropolyacid Catalysts for Oxidative Dehydrogenation of Propane. Appl. Catal., A 1999, 185, 283.
37. Okuyama, T.; Mizuno, N.; Misono, M. Catalytic Chemistry of Heteropoly Compounds. Adv. Catal. 1996, 41, 113.
38. Mizuno, N.; Misono, M. Heterogeneous Catalysis. Chem. Rev. 1998, 98, 199.
39. 3+ Species. Catal. Today 2000, 61, 203.