Sodium metavanadate catalyzed direct hydroxylation of benzene to phenol with hydrogen peroxide in acetonitrile medium

作者: Min Jian , Liangfang Zhu , Jinyue Wang , Jin Zhang , Guiying Li

DOI: 10.1016/J.MOLCATA.2006.02.054

关键词:

摘要: Abstract The homogenous liquid-phase direct catalytic oxidation of benzene to phenol was performed at room temperature in acetonitrile solvent using sodium metavanadate as the catalyst and hydrogen peroxide oxidant. effects various reaction parameters, such acidity system, temperature, time amount used, were studied. Under optimized conditions, a yield 13.5% with selectivity 94% obtained. variation vanadium species during studied by situ 51V-NMR method. It found that existed VO2+ before reaction. In presence peroxide, might be transferred peroxovanadate species, HVO(O2)2, VO(O2)+, which oxidized exerting performance. A cycle involving above mechanism proposed.

参考文章(24)
Shu-ichi Niwa, Muthusamy Eswaramoorthy, Jalajakumari Nair, Anuj Raj, Naotsugu Itoh, Hiroshi Shoji, Takemi Namba, Fujio Mizukami, A One-Step Conversion of Benzene to Phenol with a Palladium Membrane Science. ,vol. 295, pp. 105- 107 ,(2002) , 10.1126/SCIENCE.1066527
A.A. Ivanov, V.S. Chernyavsky, M.J. Gross, A.S. Kharitonov, A.K. Uriarte, G.I. Panov, Kinetics of benzene to phenol oxidation over Fe-ZSM-5 catalyst Applied Catalysis A-general. ,vol. 249, pp. 327- 343 ,(2003) , 10.1016/S0926-860X(03)00224-2
George D Vulpescu, Matthijs Ruitenbeek, Lambert L van Lieshout, Luci A Correia, Dick Meyer, Paul P.A.C Pex, One-step selective oxidation over a Pd-based catalytic membrane; evaluation of the oxidation of benzene to phenol as a model reaction Catalysis Communications. ,vol. 5, pp. 347- 351 ,(2004) , 10.1016/J.CATCOM.2004.04.002
Kenji Nomiya, Kei Hashino, Yukihiro Nemoto, Mai Watanabe, Oxidation of toluene and nitrobenzene with 30% aqueous hydrogen peroxide catalyzed by vanadium(V)-substituted polyoxometalates Journal of Molecular Catalysis A-chemical. ,vol. 176, pp. 79- 86 ,(2001) , 10.1016/S1381-1169(01)00258-8
Heike Ehrich, Heinz Berndt, Marga-Martina Pohl, Klaus Jähnisch, Manfred Baerns, Oxidation of benzene to phenol on supported Pt-VOx and Pd-VOx catalysts Applied Catalysis A-general. ,vol. 230, pp. 271- 280 ,(2002) , 10.1016/S0926-860X(02)00040-6
Stephen E. O'Donnell, Michael T. Pope, Applications of vanadium-51 and phosphorus-31 nuclear magnetic resonance spectroscopy to the study of iso- and hetero-polyvanadates Journal of the Chemical Society, Dalton Transactions. pp. 2290- 2297 ,(1976) , 10.1039/DT9760002290
M. Bonchio, V. Conte, Fulvio Di Furia, G. Modena, Metal catalysis in oxidation by peroxides. 31. The hydroxylation of benzene by VO(O2)(PIC)(H2O)2: mechanistic and synthetic aspects Journal of Organic Chemistry. ,vol. 54, pp. 4368- 4371 ,(1989) , 10.1021/JO00279A027
Karin Lemke, Heike Ehrich, Ursula Lohse, Heinz Berndt, Klaus Jähnisch, Selective hydroxylation of benzene to phenol over supported vanadium oxide catalysts Applied Catalysis A-general. ,vol. 243, pp. 41- 51 ,(2003) , 10.1016/S0926-860X(02)00535-5