Aluminosilicate obtained by sol-gel process as support for an anionic iron porphyrin: Development of a selective and reusable catalyst for oxidation reactions

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 349, Issue 1-3, 2009, Pages 162-169

  Machado, Guilherme Sippel ^a   Castro, Kelly Aparecida Dias de Freitas ^a   de Lima, Omar José ^b   Nassar, Eduardo José ^b   Ciuffi, Kátia Jorge ^b   Nakagaki, Shirley ^a  

^a FEDERAL UNIVERSITY OF PARANÁ   (Brazil)

^b UNIVERSIDADE DE FRANCA   (Brazil)

Author keywords

Aluminosilicate; Iron porphyrin; Oxidation catalysis; Sol gel process; Supported catalyst

Indexed keywords

ABSORPTION SPECTROSCOPY; ALUMINOSILICATES; CATALYSIS; CATALYTIC OXIDATION; ELECTRON RESONANCE; ELECTRON SPIN RESONANCE SPECTROSCOPY; GELATION; GELS; INFRARED SPECTROSCOPY; IRON COMPOUNDS; NANOSTRUCTURED MATERIALS; OXIDATION; OXYGEN; PARAMAGNETIC RESONANCE; PARAMAGNETISM; PORPHYRINS; SOL-GEL PROCESS; SOL-GELS; SOLS; SPECTROSCOPIC ANALYSIS; X RAY DIFFRACTION ANALYSIS;

CATALYTIC ACTIVITY; CYCLOOCTENE; ELECTRON PARAMAGNETIC RESONANCE; HETEROGENEOUS CATALYST; IMMOBILIZATION RATES; IMMOBILIZED CATALYSTS; IODOSYLBENZENE; IRON PORPHYRIN; MAGNETIC STIRRING; N-HEPTANES; NITROGEN ABSORPTION; ORGANIC SUBSTRATE; OXIDATION CATALYSIS; OXIDATION REACTIONS; OXYGEN DONORS; REUSABLE CATALYSTS; SELECTIVE OXIDATION; SUPPORTED CATALYST;

CATALYST SUPPORTS;

ALUMINUM SILICATE; CYCLOHEXANE; HEMATIN; HEPTANE; IODOSOBENZENE; METALLOPORPHYRIN; NITROGEN; OXYGEN; PORPHYRIN;

ABSORPTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ELECTRON SPIN RESONANCE; INFRARED SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 70349115006     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2009.08.013     Document Type: Article

References (38)

1. Mansuy D. A brief history of the contribution of metalloporphyrin models to cytochrome P450 chemistry and oxidation catalysis. C. R. Chim. 10 (2007) 392-413
2. Groves J.T. High-valent iron in chemical and biological oxidations. J. Inorg. Biochem. 100 (2006) 434-447
3. El-Awady A.A., Wilkins P.C., and Wilkins R.G. Kinetic aspects of the iron(III)-tetrakis(para-sulfonatophenyl)porphine system. Inorg. Chem. 24 (1985) 2053-2057
4. Bedioui F. Zeolite-encapsulated and clay-intercalated metal porphyrin, phthalocyanine and schiff-base complexes as models for biomimetic oxidation catalysts-an overview. Coord. Chem. Rev. 144 (1995) 39-68
5. Machado G.S., Castro K.A.D.F., Wypych F., and Nakagaki S. Immobilization of metalloporphyrins into nanotubes of natural halloysite toward selective catalysts for oxidation reactions. J. Mol. Catal. A: Chem. 283 (2008) 99-107
6. Groves J.T., and Nemo T.E. Epoxidation reactions catalyzed by iron porphyrins-oxygen-transfer from iodosylbenzene. J. Am. Chem. Soc. 105 (1983) 5786-5791
7. Appleton A.J., Evans S., and Smith J.R.L. Allylic oxidation and epoxidation of cycloalkenes by iodosylbenzene catalysed by iron(III) and manganese(III) tetra(dichlorophenyl)porphyrin: the marked influence of ring size on the rate of allylic oxidation. J. Chem. Soc. Perkin Trans. 2 (1995) 281-285
8. Makris T.M., Koenig K., Schlichting I., and Sligar S.G. The status of high-valent metal oxo complexes in the P450 cytochromes. J. Inorg. Biochem. 100 (2006) 507-518
9. Iamamoto Y., Idemori Y.M., and Nakagaki S. Cationic ironporphyrins as catalyst in comparative oxidation of hydrocarbons-homogeneous and supported on inorganic matrices systems. J. Mol. Catal. A: Chem. 99 (1995) 187-193
10. Nakagaki S., Xavier C.R., Wosniak A.J., Mangrich A.S., Wypych F., Cantão M.P., Denicoló I., and Kubota L.T. Synthesis and characterization of zeolite-encapsulated metalloporphyrins. J. Colloid Surf. A 168 (2000) 261-276
11. Machado A.M., Wypych F., Drechsel S.M., and Nakagaki S. Study of the catalytic behavior of montmorillonite/iron(III) and Mn(III) cationic porphyrins. J. Colloid Interface Sci. 254 (2002) 158-164
12. Nakagaki S., Benedito F.L., and Wypych F. Anionic iron(III) porphyrin immobilized on silanized kaolinite as catalyst for oxidation reactions. J. Mol. Catal. A: Chem. 217 (2004) 121-131
13. Nakagaki S., Machado G.S., Halma M., Marangon A.A.S., Castro K.A.D.F., Mattoso N., and Wypych F. Immobilization of iron porphyrins in tubular kaolinite obtained by an intercalation/delamination procedure. J. Catal. 242 (2006) 110-117
14. Halma M., Bail A., Wypych F., and Nakagaki S. Catalytic activity of anionic iron(III) porphyrins immobilized on grafted disordered silica obtained from acidic leached chrysotile. J. Mol. Catal. A: Chem. 243 (2006) 44-51
15. Nakagaki S., Castro K.A.D.F., Machado G.S., Halma M., Drechsel S.M., and Wypych F. Catalytic activity in oxidation reactions of anionic iron(III) porphyrins immobilized on raw and grafted chrysotile. J. Braz. Chem. Soc. 17 (2006) 1672-1678
16. Nakagaki S., Wypych F., Halma M., Benedito F.L., Friedermann G.R., Bail A., Machado G.S., and Drechsel S.M. Immobilization of metalloporphyrins in different inorganic supports as a strategy to obtain efficient and selective catalysts to oxidation reactions. Met. Mater. Proc. 17 (2005) 363-380
17. de Oliveira D.C., Sacco H.C., Nascimento O.R., Iamamoto Y., and Ciuffi K.J. Amino ironporphyrinosilica hybrid materials. J. Non-Cryst. Sol. 284 (2001) 27-35
18. Hench L.L., and West J.K. The sol-gel process. Chem. Rev. 90 (1990) 33-72
19. 2 xerogels prepared from aluminium nitrate nonahydrate and tetraethylorthosilicate. J. Mater. Chem. 9 (1999) 1307-1312
20. Ciuffi K.J., Nassar E.J., Rocha L.A., da Rocha Z.N., Nakagaki S., Mata G., Trujillano R., Vicente M.A., Korili S.A., and Gil A. Preparation and characterization of new Ni-aluminosilicate catalysts and their performance in the epoxidation of (Z)-cyclooctene. Appl. Catal. A: Gen. 319 (2007) 153-162
21. Antoni E., Montagne L., Daviero S., Palavit G., Bernard J., Wattiaux A., and Vezin H. Structural characterization of iron-alumino-silicate glasses. J. Non-Cryst. Sol. 345 (2004) 66-69
22. Sharefkin J.G., and Saltzmann H. Characterization of iodobenzene and its homologs by formation of polyvalent iodine derivatives with peracetic acid. Anal. Chem. 35 (1963) 1428-11428
23. Lucas J., Kennedy E.R., and Forno M.W. Iodosobenzene. Org. Synth. 43 (1963) 483-484
24. Lindsey J.S. Rothermund and Adler-Longo reactions revisited-synthesis of tetraphenylporphyrins under equilibrium conditions. J. Org. Chem. 54 (1987) 827-836
25. Adler A., and Longo F.R. Mechanistic investigations of porphyrin syntheses. I. Preliminary studies on ms-tetraphenylporphin. J. Am. Chem. Soc. 86 (1964) 3145-3149
26. Prado A.G.S., Sales A.A., Carvalho R.M., Rubim J.C., and Airoldi C. Immobilization of 5-amino-1,3,4-thiadiazole-thiol onto silica gel surface by heterogeneous and homogeneous routes. J. Non-Cryst. Sol. 333 (2004) 61-67
27. 3 films. J. Lumin. 121 (2006) 95-101
28. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. Part A. Ed. (1997), Wiley Inter Science, New York p. 192
29. Douglas B., McDaniel D., and Alexander J. Concepts and Models of Inorganic Chemistry. third ed. (1994), Wiley, Canada
30. Fernandez-Jimenez A., Vallepu R., Terai T., Palomo A., and Ikeda K. Synthesis and thermal behavior of different aluminosilicate gels. J. Non-Cryst. Sol. 352 (2006) 2061-2066
31. Piovezan C., Castro K.A.D.F., Drechsel S.M., and Nakagaki S. Epoxidation using non-heme iron complexes in solution and immobilized on silica gel as catalysts. Appl. Catal. A: Gen. 293 (2005) 97-104
32. Dolphin D., Traylor T., and Xie L.Y. Polyhaloporphyrins: unusual ligands for metals and metal-catalyzed oxidations. Acc. Chem. Res. 20 (1997) 251-259
33. Collman J.P., Tanaka H., Hembre R.T., and Brauman J.I. Metalloporphyrin-catalyzed oxidation of saturated-hydrocarbons with sodium-chlorite. J. Am. Chem. Soc. 112 (1990) 3689-3690
34. Papacídero A.T., Rocha L.A., Caetano B.L., Molina E., Sacco H.C., Nassar E.J., Martinelli Y., Mello C., Nakagaki S., and Ciuffi K.J. Preparation and characterization of spherical silica-porphyrin catalysts obtained by the sol-gel methodology. Colloids Surf. A 275 (2006) 27-35
35. Iamamoto Y., Assis M.D., Ciuffi K.J., Sacco H.C., Iwamoto L., Melo A.J.B., Nascimento O.R., and Prado C.M.C. Factors which affect the catalytic activity of iron(III) meso tetrakis(2,6-dichlorophenyl)porphyrin chloride in homogeneous system. J. Mol. Catal A: Chem. 109 (1996) 189-200
36. Thomas M.J., Raja R., Sankar G., and Bell R.G. Molecular sieve catalysts for the regioselective and shape-selective oxyfunctionalization of alkanes in air. Acc. Chem. Res. 34 (2001) 191-200
37. Cook B.R., Reinert T.J., and Suslick K.S. Shape selective alkane hydroxylation by metalloporphyrin catalysts. J. Am. Chem. Soc. 108 (1986) 7281-7286
38. Martinez-Lorente M.A., Battioni P., Klemiss W., Bartoli J.F., and Mansuy D. Manganese porphyrins covalently bound to silica and montmorillonite K10 as efficient catalysts for alkene and alkane oxidation by hydrogen peroxide. J. Mol. Catal. A: Chem. 113 (1996) 343-353