Catalytic activities of polymer-supported metal complexes in oxidation of phenol and epoxidation of cyclohexene

Polymers for Advanced Technologies

Volumn 19, Issue 3, 2008, Pages 186-200

  Gupta, K C ^a   Sutar, A K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY ROORKEE   (India)

Author keywords

Catalysis; Cyclohexene; Metal complexes; Oxidation; Phenol

Indexed keywords

ACTIVATION ENERGY; CATALYSIS; CATALYST ACTIVITY; COMPLEXATION; EPOXIDATION; HYDROGEN PEROXIDE; OXIDATION; PHENOLS; POLYSTYRENES; THERMODYNAMIC STABILITY;

MOLAR RATIO; POLYSTYRENE BEADS;

METAL COMPLEXES;

ACTIVATION ENERGY; CATALYSIS; CATALYST ACTIVITY; COMPLEXATION; EPOXIDATION; HYDROGEN PEROXIDE; METAL COMPLEXES; OXIDATION; PHENOLS; POLYSTYRENES; THERMODYNAMIC STABILITY;

CATALYST; CROSS LINKING; HYDROGEN PEROXIDE; OXIDATION; POLYSTYRENE; THERMAL STABILITY;

EID: 42149188935     PISSN: 10427147     EISSN: 10991581     Source Type: Journal    
DOI: 10.1002/pat.994     Document Type: Article

References (44)

1. Tong J, Zhang Y, Li Z, Xia C. Highly effective catalysts of natural polymer supported salophen Mn(III) complexes for aerobic oxidation of cyclohexene. J. Mol. Catal. A: Chem. 2006; 249: 47-52.
2. Chang Y, Zha F, Su B, Wang Y. Oxidation of styrene with molecular oxygen catalyzed by polymer supported o-aminobenzoic acid salicylaldehyde Schiff case copper(II) complexes. J. Macrmol. Sci. Pure Appl. Chem. 2006; 43: 923-931.
3. Ding K, Wang Z, Wang X, Liang Y, Wang X. Microencapsulated linear polymers: soluble heterogeneous catalysts. Chemistry - A Eur. J. 2006; 12: 5188-5197.
4. 202. J. Mol. Catal. A: Chem. 2006; 255: 249-253.
5. Mckenna TF, Soares JBP. Single particle modelling for olefin polymerization on supported catalysts: a review and proposals for future developments. Chem. Engg. Sci. 2001; 56: 3931.
6. Nakayama Y, Bando H, Sonobe Y, Fuzita T. Olefin polymerization behavior of bis (phenoxy-imine) Zr, Ti and V complexes with MgC12-based cocatalysts. J. Mol. Catal. A: Chem. 2004; 213: 141-1150.
7. Akelah A, Rehab A, Kenawy ER, Zeid MS, Abou MS. Catalytic activity of polymer-montmorillonites in chemical reactions. J. Appl. Polym. Sci. 2006; 101: 1121-1129.
8. Baj S, Siewniak A, Socha B. Synthesis of dialkyl peroxides in the presence of polymer supported phase-transfer ctalysts. Appl. Catal. A: Gen. 2006; 309: 85-90.
9. Kureshy RI, Khan NH, Abdi SHR, Ahmad I, Singh S, Jasra RV. Immobilization of dicationic Mn(III) salen in the interlayers of montmorillonite clay for enantioselective epoxidation of nonfunctionalized alkenes. J. Catal. 2004; 221: 234-240.
10. Blaz E, Pielichowski J. Polymer-supported cobalt (II) catalysts for the oxidation of alkenes. Molecules 2006; 11: 115.
11. Canali L, Cowan E, Gibson CL, Sherrington DC, Delueze H. Remarkable matrix effect in polymer supported Jacobson's alkene epoxidation catalysts. Chem. Commun. 1998; 23: 2501-2508.
12. Salavati-Niasari M, Salemi P, Davar F. Oxidation of cyclohexene with tert- butylhydroperoxide and hydrogen peroxide catalyzed by Cu(II), Ni(II),Co(II), and Mn(II) complexes of N,N′-bis(α-methylsalicylidene) -2,2-dimethy-2,2-dimethylpropane-1,3-diamaine, supported on alumina. J. Mol. Catal. A: Chem. 2005; 238: 215-221
13. Santeri P, Tapio S, Barbro L, Paivi P. Propylene copolymerization with non-conjugated dienes and α-olefins using supported metallocene catalyst. Polymer 2004; 45: 2099-2110.
14. AlObaidi F, Ye Z, Zhu S. Ethylene polymerization with silica-supported nickel-diimine catalyst: effect of support and polymerization conditions on catalyst activity and polymer properties. Macromol. Chem. Phys. 2003; 204: 1653-1659.
15. Casagrande Adriana CA, Tavares Tatiana TdaR, Kuhn Maria Cristina A, Casagrande Osvaldo L, dos Santos Joao HZ, Teranishi T. Tris(pyrazolyl) borate imido vanadium (V) compound immobilized on inorganic supports and its use in ethylene polymerization. J. Mol. Catal. A: Chem. 2004; 212: 267-275.
16. Wang R-M, Zhang Z-L, Lou J-F, Wang Y-P, Song P-F, Xia C-G. Preparation and catalytic oxidation properties of inorganic polymer encapsulated metal complexes. Polym. Adv. Technol. 2004; 15: 48-51.
17. El-Hamshary H, Assubaie Fahad N. Aqueous oxidation of 2,6-dimethylphenol with hydrogen peroxide catalyzed by transition metal complexes supported on polyvinyl pyridinium salts. J. Macromol. Sci., Pure Appl. Chem. 2004; A41: 107-114.
18. Doherty S, Knight Julian G, Betham M. The first insoluble polymer bound palladium complexes of 2-pyridyldiphenylphosphine: highly efficient catalysts for alkoxy carbonylation of terminal alkynes. Chem. Commun. 2006; 1: 88-90.
19. Fuerte A, Iglesias M, Sanchez F, Corma A. Chiral dioxomolybdenum(VI) and oxovanadium(V) complexes anchored on modified USY-zeolite and mesoporous MCM41 as solid selective catalyst for oxidation of sulfides or sulfones. J. Mol. Catal A: Chem. 2004; 211: 227-235.
20. 2 anchoring on catalyst actvity and on polymer properties. Appl. Catal. A: Gen. 2004; 261: 57-67.
21. Zsigmond A, Bogar K, Notheisz F. Comparative study of "ship-in-a-bottle" and anchored heterogenized Rh complexes. J. Catal. 2003; 213: 103-108.
22. Gournis D, Louloudi M, Karakassides MA, Kolokytha C, Mitopoulou K, Hadjiliadis N. Heterogeneous clay-manganese(II) oxidation catalyst. Mater. Sci. Eng. 2002; C22: 113-116.
23. Sherrington DC. Polymer-supported metal complex alkene epoxidation catalysts. Catal. Today 2000; 57: 87-104.
24. Silva AR, Martins M, Freitas MMA, Valente A, Freire C, de Castro B, Figueiredo JL. Immobilisation. of amine-functionalized nickel(II) Schiff base complexes onto activated carbon treated with thionyl chloride. [i Microporous Mesoporous Mater. 2002; 55: 275-284.
25. Kim G-J, Park D-W. The catalytic activity of new chiral salen complexes immobilized on MCM-41 in the asymmetric hydrolysis of epoxides to diols. Catal. Today 2000; 63: 537-547.
26. Kowalak S, Weiss RC, Balkus KJ Jr. Zeolite encapsulated palladium(salen), a selective hydrogenation catalyst. J. Chem. Soc. Chemi. Commun. 1991; 1: 57-58.
27. Owsik I, Kolarz BN, Jezierska J. Oxidation of 2,6-ditertbutylphenols to diphenoquinones catalyzed by sciff base-Cu(II) systems immobolized on polymer support. J. Catal. Lett. 2006; 107: 197-203.
28. Safarov RZ, Kastonozhkina OI, Zharmagambetova AK. Oxidation of cyclohexene on polymer modified Mn ferrocyanide complex on aluminosilicate carrier. Senya Khimicheskaya 2005; 3: 3-10.
29. Wang C, Xin W, Fu X, Zhang Y, Yang Y. Studies on catalytic polarographic hydrogen wave in iridium(IV)-cysteine-hydrochloric acid and its application. Fenxi Huaxue 1992; 20: 368-372.
30. Hermann WA, Fisher RW, Scherer W, Ranch MU. Multiple bonding between main group elements and transition metals. 122. Methyltrioxorhenium(VII) as an epoxidation catalyst: structure of the active species and the mechanism of catalysis. Angew. Chem. 1993; 105: 1209-1212.
31. Herrmann Wolfgang A, Fischer Richard W, Marz Dieter W. Multiple bonding between main group elements and transition metals. 100. Part 2. Methyltrioxorhenium as catalyst for olefin oxidation. Angew. Chem. 1991; 103: 1706.
32. Hashemi MM, Beni, Ai Y. Oxidation of phenols to quinones by oxygen catalyzed by a mixture of cobalt and manganese salts of p-Aminobenzoic acid supported on silica gel. J. Chem. Res. (S) 1998; 3: 138-1139.
33. Miller MM, Sherrington DC. Alkene epoxidations catalyzed by Mo(VI) supported on imidazole-containing polymers. I. Synthesis, characterization, and activity of catalysts in the epoxidation of cyclohexene. J. Catal. 1995; 152: 368-376.
34. Olason G, Sherrington DC. Oxidation of cyclohexene by tert-butyl hydroperoxide and dioxygen catalyzed by polybenzimidazole-supported Cu, Mn, Fe, Ru and Ti complexes. React. Funct. Polym. 1999; 42: 163-172.
35. Gupta KC, Abdulkadir HK, Chand S. Synthesis of polymer anchored N,N′-bis(3-allyl salicylidene)o-phenylenediamine cobalt(II) Schiff base complexes and its catalytic activity in decomposition of hydrogen peroxoide. J. Mol. Catal. A: Chem. 2003; 202: 253-268.
36. Gupta KC, Abdulkadir HK, Chand S. Polymer supported N, N′-bis(salicylidne)hydrazine Co(II) Schiff base complex and its catalytic activity. J. Macromol. Sci. Pure Appl. Chem. 2002; [b A39: 1451-1474.
37. Vogel Al. Textbook of Practical Organic Chemistry, 1978. ELBS and Longman: London.
38. Drago RS, Gaul J, Zombeck A, Straub DK. Preparation and catalytic oxidizing potential of polymer supported chelating amine and Schiff base complexes. J. Am. Chem. Soc. 1980; 102: 1033-1038.
39. He Helen S, Zhang C, Ng Chris K-W, Toy Patrick H. Polystyrene-Supported triphenylarsines: useful ligands in palladium-catalyzed aryl halide homocoupling reactions and a catalyst for alkene epoxidation using hydrogen peroxide. Tetrahedran 2005; 61: 12053-12057.
40. Hankova L, Holub L, Jerabek K. Relation between functionalization. degree and activity of strongly acidic polymer supported catalysts. React. Funct. Polym. 2006; 66: 592-598.
41. Yoon Ji W, Chang J-S, Lee H-D, Kim T-J, Jhung Sung H. Trimerization of isobutene over cation exchange resins: effect of physical properties of the resins and reaction conditions. J. Mol. Catal. A: Chem. 2006; 260: 181-186.
42. Leinonen S-M, Sherrington DC. Epoxidation of alkenes using equimolar levels of t-BHP catalyzed by polybenzimidazole (PBI)-supported molybdenum(VI). J. Chem. Res. (S) 1999; 9: 572-573.
43. Zhang Y, Zhao J, He L, Zhao D, Zhang S. Manganese (III) salen complex anchored onto MCM-41 as catalyst for the aerobic epoxidation of olefins. Microporous Mesoporous Mater. 2000; 94: 159-165.
44. 2 using the Schiff base complexes as mimetic peroxidases. Transit. Met. Chem. 2000; 29: 388-393.