苯与双氧水在高效钼钒磷杂多酸催化剂上的羟基化

CIESC Journal

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苯与双氧水在高效钼钒磷杂多酸催化剂上的羟基化

张富民; 郭麦平; 葛汉青; 王军

State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineer-ing, Nanjing University of Technology, Nanjing 210009, China

收稿日期:2006-10-26 修回日期:1900-01-01 出版日期:2007-12-28 发布日期:2007-12-28
通讯作者: 张富民

Hydroxylation of benzene with hydrogen peroxide over highly efficient molybdovanadophosphoric heteropoly acid catalysts

ZHANG Fumin; GUO Maiping; GE Hanqing; WANG Jun

State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineer-ing, Nanjing University of Technology, Nanjing 210009, China

Received:2006-10-26 Revised:1900-01-01 Online:2007-12-28 Published:2007-12-28
Contact: ZHANG Fumin

摘要/Abstract

摘要： Keggin type molybdovanadophosphoric heteropoly acids, H3+nPMo12－nVnO40 (n＝1—3), were prepared by a novel environmentally benign method, and their catalytic performances were evaluated via hydroxylation of benzene to phenol with hydrogen peroxide as oxidant in a mixed solvent of glacial acetic acid and acetonitrile. Various reaction parameters, such as reaction time, reaction temperature, ratio of benzene to hydrogen peroxide, concentration of aqueous hydrogen peroxide, ratio of glacial acetic acid to acetonitrile in solvent and catalyst concentration, were changed to obtain an optimal reaction conditions. H3+nPMo12－nVnO40 (n＝1—3) are revealed to be highly efficient catalyst for hydroxylation of benzene. In case of H5PMo10V2O40, a conversion of benzene of 34.5% with the selectivity of phenol of 100% can be obtained at the optimal reaction conditions.

关键词: hydroxylation;heteropoly acid;phenol;benzene

Abstract: Keggin type molybdovanadophosphoric heteropoly acids, H3+nPMo12－nVnO40 (n＝1—3), were prepared by a novel environmentally benign method, and their catalytic performances were evaluated via hydroxylation of benzene to phenol with hydrogen peroxide as oxidant in a mixed solvent of glacial acetic acid and acetonitrile. Various reaction parameters, such as reaction time, reaction temperature, ratio of benzene to hydrogen peroxide, concentration of aqueous hydrogen peroxide, ratio of glacial acetic acid to acetonitrile in solvent and catalyst concentration, were changed to obtain an optimal reaction conditions. H3+nPMo12－nVnO40 (n＝1—3) are revealed to be highly efficient catalyst for hydroxylation of benzene. In case of H5PMo10V2O40, a conversion of benzene of 34.5% with the selectivity of phenol of 100% can be obtained at the optimal reaction conditions.

Key words: hydroxylation, heteropoly acid, phenol, benzene

张富民, 郭麦平, 葛汉青, 王军. 苯与双氧水在高效钼钒磷杂多酸催化剂上的羟基化[J]. CIESC Journal.

ZHANG Fumin, GUO Maiping, GE Hanqing, WANG Jun. Hydroxylation of benzene with hydrogen peroxide over highly efficient molybdovanadophosphoric heteropoly acid catalysts[J]. .

参考文献

1 Mizuno, N., Misono, M., “Heterogenous catalysis”, Chem. Rev. Sci. Eng., 98, 199—217(1998).
2 Keggin, J.F., “Structure of the molecule of 12-phosphotungstic acid”, Nature, 131, 908—909(1933).
3 Kozhevnikov, I.V., “Heteropoly acids and re-lated-compounds as catalysts for fine chemical synthe-sis”, Catal. Rev. Sci. Eng., 37(2), 311—352(1995).
4 Zhang, F.M., Yuan, C.S., Wang, J., Kong, Y., Zhu, H.Y., Wang, C.Y., “Synthesis of fructone over dealmuinated USY supported heteropoly acid and its salt catalysts”, J. Mol. Catal. A Chem., 247, 130—137(2006).
5 Shinachi, S., Matsushita, M., Yamaguchi, K., Mizuno, N., “Oxidation of adamantane with 1 atm molecular oxygen by vanadium-substituted polyoxometalates”, J. Catal., 233, 81—89(2005).
6 Okuhara, T., Mizuno, N., Misono, M., “Catalytic chem-istry of heteropoly compounds”, Adv. Catal., 41, 113—252(1996).
7 Zhang, W.Z., Wang, J.L., Tanev, P.T., Pinnavaia, T.J., “Catalytic hydroxylation of benzene over transi-tion-metal substituted hexagonal mesoporous silicas”, Chem. Commun., (8), 979—980(1996).
8 Bengoa, J.F., Gallegos, N.G., Marchetti, S.G., Alvarez, A.M., Cagnoli, M.V., Yeramian, A.A., “Influence of TS-1 structural properties and operation conditions on venzene catalytic oxidation with H2O2”, Micropor. Mesopor. Ma-ter., 24, 163—172(1998).
9 Chen, Y.W., Lu, Y.H., “Characteristics of V-MCM-41 and its catalytic properties in oxidation of benzene”, Ind. Eng. Chem. Res., 38, 1893—1903(1999).
10 Das, S.K., Kumar, A.J., Nandrajog, S., “Poly-mer-supported VO2+ schiff-base catalyst for hydroxyla-tion of benzene”, Tetrahedron Lett., 36, 7909—7912(1995).
11 Kuznetsova, L.I., Detusheva, L.G., Fedotov, M.A., Lik-holobov, V.A., “Catalytic properties of heteropoly com-plexes containing Fe(III) ions in benzene oxidation by hydrogen peroxide”, J. Mol. Catal. A Chem., 111, 81—90(1996).
12 Kuznetsova, N.I., Kuznetsova, L.I., Likholobov, V.A., “Catalytic properties of Cr-containing heteropolytung-states in H2O2 participated reactions: H2O2 decomposi-tion and oxidation of unsaturated hydrocarbons with H2O2”, J. Mol. Catal. A Chem., 108, 135—143(1996).
13 Seo, Y.J., Mukai, Y., Tagawa, T., Goto, S., “Phenol syn-thesis by liquid-phase oxidation of benzene with mo-lecular oxygen over iron-heteropoly acid”, J. Mol. Catal. A Chem., 120, 149—154(1997).
14 Parsoni, L.C., Cruz, A.T., Buffon, R., Schuchardt, U., “Complexes of palladium(II) and platinum(II) with the heteropolyanion as catalytically active species in benzene oxidation”, J. Mol. Catal. A Chem., 120, 117—123(1997).
15 Nomiya, K., Yagishita, K., Nemoto, Y., Kamataki, T.A., “Functional action of Keggin-type mono-vanadium(V)- substituted heteropolymolybdate as a single species on catalytic hydroxylation of benzene in the presence of hy-drogen peroxide”, J. Mol. Catal. A Chem., 126, 43—53(1997).
16 Alekar, N.A, Indira, V., Hallingudi, S.B., Srinivas, D., Gopinathan, S., Gopinathan, C., “Kinetics and mecha-nism of selective hydroxylation of benzene catalysed by vanadium substituted heteropolymolybdates”, J. Mol. Catal. A Chem., 164, 181—189(2000).
17 Zhang, J., Tang, Y., Li, G.Y., Hu, C.W., “Room tempera-ture direct oxidation of benzene to phenol using hydro-gen peroxide in the presence of vanadium-substituted heteropolymolybdates”, Appl. Catal. A Gen., 278, 251—261(2005).
18 Zhang, F.M., Guo, M.P., Ge, H.Q., Wang, J., “A new method for synthesis of molybdovanadophosphoric het-eropoly acids and their catalytic activities”, Chem. Ind. Eng. Prog., 25(10), 1171—1174(2006). (in Chinese)
19 Tsigdinos, G.A., Hallada, C.J., “Molybdovanadophos-phoric acids and their salts (I) Investigation of methods of preparation and characterization”, Inorg. Chem., 7, 437—441(1968).
20 Ishida, M.A., 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(4), 847—854(1999).
21 Gao, F.X., Hua, R.M., “Highly efficient K7NiV13O38-catalyzed hydroxylation of aromatics with aqueous hydrogen peroxide (30%)”, Appl. Catal. A Gen., 270, 223—226(2004).

苯与双氧水在高效钼钒磷杂多酸催化剂上的羟基化

Hydroxylation of benzene with hydrogen peroxide over highly efficient molybdovanadophosphoric heteropoly acid catalysts

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