Heteropolyanion-based ionic hybrid solid: A green bulk-type catalyst for hydroxylation of benzene with hydrogen peroxide

Chemical Engineering Journal

Volumn 173, Issue 2, 2011, Pages 620-626

  Leng, Yan ^a   Wang, Jun ^a   Zhu, Dunru ^a   Shen, Lei ^b   Zhao, Pingping ^a   Zhang, Mingjue ^a  

^a NANJING TECH UNIVERSITY   (China)

^b CHANGSHU INSTITUTE OF TECHNOLOGY   (China)

Author keywords

Heterogeneous catalysis; Heteropolyacids; Hybrid catalysts; Hydroxylation of benzene; Phenol

Indexed keywords

ACTIVE CENTER; BET SURFACE AREA; BIPHASIC REACTION; CATALYTIC PERFORMANCE; HETEROPOLY ACIDS; HETEROPOLY ANIONS; HYBRID CATALYSTS; HYBRID SOLIDS; HYDROXYLATION OF BENZENE; IONIC INTERACTION; LIQUID SOLIDS; ORGANIC CATIONS; REACTION CONDITIONS; REDOX PAIRS; XRD;

BENZENE; BENZENE REFINING; BUTANE; CATALYSIS; HYDROGEN PEROXIDE; HYDROXYLATION; IONIC LIQUIDS; PHENOLS; POSITIVE IONS; REUSABILITY;

CATALYST ACTIVITY;

EID: 80052580690     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2011.08.013     Document Type: Article

References (47)

1. Niwa S., Eswaramoorthy M., Nair J., Raj A., Itoh N., Shoji H., Namba T., Mizukami F. A one-step conversion of benzene to phenol with a palladium membrane. Science 2002, 295:105-107.
2. Xin H., Koekkoek A., Yang Q., van Santen R., Li C., Hensen E.J.M. A hierarchical Fe/ZSM-5 zeolite with superior catalytic performance for benzene hydroxylation to phenol. Chem. Commun. 2009, 7590-7592.
3. Kusakari T., Sasaki T., Iwasawa Y. Selective oxidation of benzene to phenol with molecular oxygen on rhenium/zeolite catalysts. Chem. Commun. 2004, 99:2-993.
4. Chen X., Zhang J., Fu X., Antonietti M., Wang X. Fe-g-C3N4-catalyzed oxidation of benzene to phenol using hydrogen peroxide and visible light. J. Am. Chem. Soc. 2009, 131:11658-11659.
5. Guo Y., Zhang X., Zou H., Liu H., Wang J., Yeung K.L. Pd-silicalite-1 composite membrane for direct hydroxylation of benzene. Chem. Commun. 2009, 589:8-5900.
6. Wang X., Guo Y., Zhang X., Wang Y., Liu H., Wang J., Qiu J., Yeung K.L. Catalytic properties of benzene hydroxylation by TS-1 film reactor and Pd-TS-1 composite membrane reactor. Catal. Today 2010, 156:288-294.
7. Balducci L., Bianchi D., Bortolo R., Daloisio R., Ricci M., Tassinari R., Ungarelli R. Direct oxidation of benzene to phenol with hydrogen peroxide over a modified titanium silicalite. Angew. Chem. Int. Ed. 2003, 42:4937-4940.
8. Chen Y.W., Lu Y.H. Characteristics of V-MCM-41 and its catalytic properties in oxidation of benzene. Ind. Eng. Chem. Res. 1999, 38:1893-1903.
9. Nomiya K., Yagishita K., Nemoto Y., Kamataki T. Functional action of Keggin type mono-vanadium(V)-substituted heteropolymolybdate as a single species on catalytic hydroxylation of benzene in the presence of hydrogen peroxide. J. Mol. Catal. A 1997, 126:43-53.
10. Zhang J., Tang Y., Li G., Hu C. Room temperature direct oxidation of benzene to phenol using hydrogen peroxide in the presence of vanadium-substituted heteropolymolybdates. Appl. Catal. A-Gen. 2005, 278:251-261.
11. Arichi J., Eternot M., Louis B. Synthesis of V-containing Keggin polyoxometalates: versatile catalysts for the synthesis of fine chemicals. Catal. Today 2008, 138:117-122.
12. Liu Y., Murata K., Inaba M. Direct oxidation of benzene to phenol by molecular oxygen over catalytic systems containing Pd(OAc)2 and heteropolyacid immobilized on HMS or PIM. J. Mol. Catal. A 2006, 256:247-255.
13. Welton T. Ionic liquids in catalysis. Coord. Chem. Rev. 2004, 248:2459-2477.
14. Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99:2071-2083.
15. Tan R., Yin D., Yu N., Jin Y., Zhao H., Yin D. Ionic liquid-functionalized salen Mn(III) complexes as tunable separation catalysts for enantioselective epoxidation of styrene. J. Catal. 2008, 255:287-295.
16. Peng J., Shi F., Deng Y.G.Y. Highly selective and green aqueous-ionic liquid biphasic hydroxylation of benzene to phenol with hydrogen peroxide. Green Chem. 2003, 5:224-226.
17. Gu Y., Li G. Ionic liquids-based catalysis with solids: state of the art. Adv. Synth. Catal. 2009, 351:817-847.
18. Rickert P.G., Antonio M.R., Firestone M.A., Kubatko K.A., Szreder T., Wishart J.F., Dietz M.L. Tetraalkylphosphonium polyoxometalate ionic liquids: novel organic-inorganic hybrid materials. J. Phys. Chem. B 2007, 111:4685-4692.
19. Bourlinos A.B., Raman K., Herrera R., Zhang Q., Archer L.A., Giannelis E.P. A liquid derivative of 12-tungstophosphoric acid with unusually high conductivity. J. Am. Chem. Soc. 2004, 126:15358-15359.
20. Qiao Y., Hou Z. Polyoxometalate-based solid and liquid salts for catalysis. Curr. Org. Chem. 2009, 13:1347-1365.
21. Li H., Qiao Y., Hua L., Hou Z., Feng B., Pan Z., Hu Y., Wang X., Zhao X., Yu Y. Imidazolium polyoxometalate: an ionic liquid catalyst for esterification and oxidative esterification. ChemCatChem 2010, 2:1165-1170.
22. Leng Y., Wang J., Zhu D., Ren X., Ge H., Shen L. Heteropolyanion-based ionic liquids: reaction-induced self-separation catalysts for esterification. Angew. Chem. Int. Ed. 2009, 48:168-171.
23. Leng Y., Wang J., Zhu D., Wu Y., Zhao P. Sulfonated organic heteropolyacid salts: recyclable green solid catalysts for esterifications. J. Mol. Catal. A: Chem. 2009, 313:1-6.
24. Zhang W., Leng Y., Zhu D., Wu Y., Wang J. Phosphotungstic acid salt of triphenyl(3-sulfopropyl)phosphonium: an efficient and reusable solid catalyst for esterification. Catal. Commun. 2009, 11:151-154.
25. Zhang W., Leng Y., Zhao P., Wang J., Zhu D., Huang J. Heteropolyacid salts of N-methyl-2-pyrrolidonium as highly efficient and reusable catalysts for Prins reactions of styrenes with formalin. Green Chem. 2011, 13:832-834.
26. Y. Leng, J. Wang, D. Zhu, M. Zhang, P. Zhao, Z. Long, J. Huang, Polyoxometalate-based amino-functionalized ionic solid catalysts lead to highly efficient heterogeneous epoxidation of alkenes with H2O2, Green. Chem. DOI:10.1039/C1GC15302A.
27. Payagala T., Huang J., Breitbach Z.S., Sharma P.S., Armstrong D.W. Unsymmetrical dicationic ionic liquids: manipulation of physicochemical properties using specific structural architectures. Chem. Mater. 2007, 19:5848-5850.
28. Anderson J.L., Ding R., Ellern A., Armstrong D.W. Structure and properties of high stability geminal dicationic ionic liquids. J. Am. Chem. Soc. 2005, 127:593-604.
29. Leng Y., Ge H., Zhou C., Wang J. Direct hydroxylation of benzene with hydrogen peroxide over pyridine-heteropoly compounds. Chem. Eng. J. 2008, 145:335-339.
30. Dupont J., Consorti C.S., Suarez P.A.Z., de Souza R.F. Preparation of 1-butyl-3-methyl imidazolium-based room temperature ionic liquids. Org. Synth. 2002, 79:236-240.
31. Ettedgui J., Neumann R. Phenanthroline decorated by a crown ether as a module for metallorganic-polyoxometalate hybrid catalysts: the wacker type oxidation of alkenes with nitrous oxide as terminal oxidant. J. Am. Chem. Soc. 2009, 131:4-5.
32. Chen J., Gao S., Xu J. Direct hydroxylation of benzene to phenol over a new vanadium-substituted phosphomolybdate as a solid catalyst. Catal. Commun. 2008, 9:728-733.
33. Brückner A., Scholz G., Heidemann D., Schneider M., Herein D., Bentrup U., Kant M. Structural evolution of H4PVMo11O40·xH2O during calcination and isobutene oxidation: new insights into vanadium sites by a comprehensive in situ approach. J. Catal. 2007, 245:369-380.
34. Yamaguchi S., Sumimoto S., Ichihashi Y., Nishiyama S., Tsuruya S. Liquid-phase oxidation of benzene to phenol over V-substituted heteropolyacid catalysts. Ind. Eng. Chem. Res. 2005, 44:1-7.
35. Duncan D.C., Chambers R.C., Hecht E., Hill C.L. Mechanism and dynamics in the H3[PW12O40]-catalyzed selective epoxidation of terminal olefins by H2O2. Formation, reactivity, and stability of {PO4[WO(O2)2]4}3- J. Am. Chem. Soc. 1995, 117:681-691.
36. Yori J.C., Grau J.M., Benitez V.M., Sepulveda J. Hydroisomerization-cracking of n-octane on heteropolyacid H3PW12O40 supported on ZrO2, SiO2 and carbon. Effect of Pt incorporation on catalyst performance. Appl. Catal. A-Gen. 2005, 286:71-78.
37. Sumimoto S., Tanaka C., Yamaguchi S., Ichihashi Y., Nishiyama S., Tsuruya S. Zinc powder as an effective reducing reagent during liquid-phase oxidation of benzene to phenol using molecular oxygen over V-substituted heteropoly acid catalysts. Ind. Eng. Chem. Res. 2006, 45:7444-7450.
38. Khatri P.K., Singh B., Jain S.L., Saina B., Sinha A.K. Cyclotriphosphazene grafted silica: a novel support for immobilizing the oxovanadium Schiff base moieties for hydroxylation of benzene. Chem. Commun. 2011, 47:1610-1612.
39. Battistel E., Tassinari R., Fornaroli M., Bonoldi L. Oxidation of benzene by molecular oxygen catalysed by vanadium. J. Mol. Catal. A 2003, 202:107-115.
40. Sakamoto T., Takagaki T., Sakakura A., Obora Y., Sakaguchi S., Ishii Y. Hydroxylation of benzene to phenol under air and carbon monoxide catalyzed by molybdovanadophosphates. J. Mol. Catal. A 2008, 288:19-22.
41. Tani M., Sakamoto T., Mita S., Sakaguchi S., Ishii Y. Hydroxylation of benzene to phenol under air and carbon monoxide catalyzed by molybdovanadophosphoric acid. Angew. Chem. Int. Ed. 2005, 44:2586-2588.
42. Yan X., Zhu P., Fei J., Li J. Self-assembly of peptide-inorganic hybrid spheres for adaptive encapsulation of guests. Adv. Mater. 2010, 22:1283-1287.
43. Misono M. Unique acid catalysis of heteropoly compounds (heteropolyoxometalates) in the solid state. Chem. Commun. 2001, 114:1-1152.
44. Misono M. Heterogeneous catalysis by heteropoly compounds: an attempt of molecular design of practical solid acid catalysts. Catal. Lett. 1992, 12:63-72.
45. Clericai M.G., Bellussi G., Romano U. Synthesis of propylene oxide from propylene and hydrogen peroxide catalyzed by titanium silicalite. J. Catal. 1991, 129:159-167.
46. Bianchi D., Bortolo R., Tassinari R., Ricci M., Vignola R. A novel iron-based catalyst for the biphasic oxidation of benzene to phenol with hydrogen peroxide. Angew. Chem. Int. Ed. 2000, 39:4321-4323.
47. Zhong Y., Li G., Zhu L., Yan Y., Wu G., Hu C. Low temperature hydroxylation of benzene to phenol by hydrogen peroxide over Fe/activated carbon catalyst. J. Mol. Catal. A 2007, 272:169-173.