Selective oxidation of styrene to 1,2-epoxyethylbenzene by hydrogen peroxide over heterogeneous phosphomolybdic acid supported on ionic liquid modified MCM-41

Chemical Engineering Journal

Volumn 260, Issue , 2015, Pages 172-177

  Wang, Bing ^a,c   Zhang, Jian ^a,b   Zou, Xiong ^a   Dong, Hongguang ^a   Yao, Pingjing ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b LIAONING SHIHUA UNIVERSITY   (China)

^c PETROCHINA COMPANY LIMITED   (China)

Author keywords

Heterogeneous reaction; Hydrogen peroxide; Phosphomolybdic acid; Selective oxidation; Styrene

Indexed keywords

CATALYST DEACTIVATION; HYDROGEN; HYDROGEN PEROXIDE; IONIC LIQUIDS; MESOPOROUS MATERIALS; OXIDATION; PEROXIDES; STYRENE;

ADSORPTION DESORPTION; HETEROGENEOUS CATALYST; HETEROGENEOUS REACTIONS; MESOPOROUS STRUCTURES; MOLAR RATIO; PHOSPHOMOLYBDIC ACID; REACTION CONDITIONS; SELECTIVE OXIDATION;

CATALYST SELECTIVITY;

EID: 84913594496     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.08.076     Document Type: Article

References (31)

1. Monnier J.R. The direct epoxidation of higher olefins using molecular oxygen. Appl. Catal. A 2001, 211:73-91.
2. Krishnan R., Vancheesan S. Polynuclear manganese complexes catalyzed epoxidation of olefins with molecular oxygen. J. Mol. Catal. A 2002, 185:87-95.
3. Melero J.A., Iglesias J., Sainz-Prado J., Frutos P., Blázquez S. Agglomeration of Ti-SBA-15 with clays for liquid phase olefin epoxidation in a continuous fixed bed reactor. Chem. Eng. J. 2008, 139:631-641.
4. Barrio L., Campos-Martin J.M., Frutos M.P., Fierro J.L.G. Alkene epoxidation with ethylbenzene hydroperoxides using molybdenum heterogeneous catalysts. Ind. Eng. Chem. Res. 2008, 47:8016-8024.
5. 2 catalyzed by supported TS-1 catalyst in a fixed-bed reactor: experiments and kinetics. Chem. Eng. J. 2013, 215-216:306-314.
6. Fraile J.M., Garcia J.I., Mayoral J.A., Vispe E. Silica-supported titanium derivatives as catalysts for the epoxidation of alkenes with hydrogen peroxide: a new way to tuneable catalytic activity through ligand exchange. J. Catal. 2000, 189:40-51.
7. Wang Q., Zhang X., Wang L., Mi Z. Kinetics of epoxidation of hydroxyl-terminated polybutadiene with hydrogen peroxide under phase transfer catalysis. Ind. Eng. Chem. Res. 2009, 48:1364-1371.
8. 3-). J. Mol. Catal. A 1985, 32:107-110.
9. Jorgensen K.A. Transition-metal-catalyzed epoxidations. Chem. Rev. 1989, 89:431-458.
10. Meanier B. Metalloporphyrins as versatile catalysts for oxidation reactions and oxidative DNA cleavage. Chem. Rev. 1992, 92:1411-1456.
11. Hoegaerts D., Sels B.F., Vos D.E., Verpoort F., Jacobs P.A. Heterogeneous tungsten-based catalysts for the epoxidation of bulky olefins. Catal. Today 2000, 60:209-218.
12. Gaspar H., Andrade M., Pereire C., Pereira A.M., Rebelo S.L.H., Araújo J.P., Pires J., Carvalho A.P., Freire C. Alkene epoxidation by manganese (III) complexes immobilized onto nanostructured carbon CMK-3. Catal. Today 2013, 203:103-110.
13. Betz D., Herrmann W.A., Kühn F.E. Epoxidation in ionic liquids: a comparison of rhenium and molybdenum catalysts. J. Organomet. Chem. 2009, 694:3320-3324.
14. Ahn J., Kim J., Ihm S., Oh C., Sherrington D.C. Epoxidation of olefins by molybdenum catalysts supported on functional polyimide particulates. Ind. Eng. Chem. Res. 2005, 44:8560-8564.
15. Corma A., Esteve P., Martinez A., Valencia S. Oxidation of olefins with hydrogen peroxide and tert-butyl hydroperoxide on Ti-beta catalyst. J. Catal. 1995, 152:18-24.
16. Elías V.R., Crivello M.E., Herrero E.R., Casuscelli S.G., Eimer G.A. Synthesis of titanium-containing mesoporous silicas as catalysts for cyclohexene epoxidation. Ind. Eng. Chem. Res. 2009, 48:9076-9082.
17. Venturello C., Alneri E., Ricci M. A new, effective catalytic system for epoxidation of olefins by hydrogen peroxide under phase-transfer conditions. J. Org. Chem. 1983, 48:3831-3833.
18. 3-) as a new class of catalysts for efficient alkene epoxidation with hydrogen peroxide. J. Org. Chem. 1988, 53:1553-1557.
19. Ishii Y., Yamawaki K., Ura T., Yamada H., Yoshida T., Ogawa M. Hydrogen peroxidation catalyzed by heteropoly acids combined with cetylpyridinium chloride: epoxidation of olefins and allylic alcohols, ketonization of alcohols and diols, and oxidative cleavage of 1,2-diols and olefins. J. Org. Chem. 1988, 53:3587-3593.
20. Choudary B.M., Prasad A.D., Swapna V., Valli V.L.K., Bhuma V. Chromium pillared clay catalysed allylic oxidation and oxidative deprotection of allyl ethers and amines: a simple and convenient procedure. Tetrahedron 1992, 48:953-962.
21. Lempers H.E.B., Sheldon R.A. Allylic oxidation of olefins to the corresponding α,β-unsaturated ketones catalyzed by chromium aluminophosphate. Appl. Catal. A 1996, 143:137-143.
22. Sakthivel A., Dapurkar S.E., Selvam P. Allylic oxidation of cyclohexene over chromium containing mesoporous molecular sieves. Appl. Catal. A 2003, 246:283-293.
23. Pillai U.R., Sahle-Demessie E., Varma R.S. Microwave-expedited olefin epoxidation over hydrotalcites using hydrogen peroxide and acetonitrile. Tetrahedron Lett. 2002, 43:2909-2911.
24. Das T.K., Chaudhari K., Nandanan E., Chandwadkar A.J., Sudalai A., Ravindranthan T., Sivasanker S. Cr-MCM-41-catalyzed selective oxidation of alkylarenes with TBHP. Tetrahedron Lett. 1997, 38:3631-3634.
25. Wang A.J., Kabe T. Fine-tuning of pore size of MCM-41 by adjusting the initial pH of the synthesis mixture. Chem. Commun. 1999, 2067-2068.
26. Kresge C.T., Leonowicz M.E., Roth W.J., Vartuli J.C., Beck J.S. Ordered mesoporous molecular sieves synthesized by a liquid-crystal template mechanism. Nature 1992, 359:710-712.
27. Rao G.R., Rajkumar T., Varghese B. Synthesis and characterization of 1-butyl 3-methylimidazolium phosphomolybdate molecular salt. Solid State Sci. 2009, 11:36-42.
28. Yang H., Zhang G., Hong X., Zhu Y. Dicyano-functionalized MCM-41 anchored-palladium complexes as recoverable catalysts for Heck reaction. J. Mol. Catal. 2004, 210:143-148.
29. Derylo-Marczewska A., Gac W., Popivnyak N., Zukocinski G., Pasieczna S. The influence of preparation method on the structure and redox properties of mesoporous Mn-MCM-41 materials. Catal. Today 2006, 114:293-306.
30. 2 route. Green Chem. 2005, 7:701-704.
31. Chakraborty B., Viswanathan B. Surface acidity of MCM-41 by in situ IR studies of pyridine adsorption [J]. Catal. Today 1999, 49:253-260.