Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide

Costa, Andréia Alves; Ghesti, Grace Ferreira; Macedo, Julio L. de; Braga, Vítor; Santos, Marcello M.; Dias, José A.; Dias, Sílvia C.L.

doi:10.1016/j.molcata.2007.12.024

Cited by 75 publications

(29 citation statements)

References 30 publications

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“…The bands observed at 470, 804, 961 and 1093 cm −1 , which are related to ν(Si-O-Si), ν s (Si-O-Si), ν(Si-OH) and ν as (Si-O-Si), respectively, are the main features of MCM-41 [34,36] and wide band at 3445 cm…”

Section: Characterization Of Heterogeneous Catalystsmentioning

confidence: 94%

“…meso-Tetraphenylporphyrin and metalloporphyrins were prepared according to the literature. [33,34] [35] using the following procedure: 7.48 g tetradecyl (trimethyl) ammonium bromide was dissolved in 80.0 g water. Then, an aqueous solution of sodium silicate (9.9 g in 30.0 g water) was added dropwise under vigorous magnetic stirring.…”

Section: Methodsmentioning

confidence: 99%

“…The heterogeneous catalysts were prepared according to literature. [34] Briefly, 0.05 g of metalloporphyrin (Fe(TPP)Cl, Mn(TPP)OAc or Cu(TPP)) was added to 0.2 g of MCM-41 in dichloromethane (20 mL). The mixture was allowed to stir at room temperature for 48 h, and then under reflux conditions for 3 h. The solid product was then washed in a Soxhlet apparatus with 200 mL of dichloromethane for 10 h. Finally, the solids were dried in air at room temperature (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

A Comparative Study of Catalytic Activity of Fe, Mn and Cu Porphyrins Immobilized on Mesoporous MCM-41 in Oxidation of Sulfides

Rayati¹,

Ruzbahani²,

Nejabat³

2017

MHC

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Section: Characterization Of Heterogeneous Catalystsmentioning

confidence: 94%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

A Comparative Study of Catalytic Activity of Fe, Mn and Cu Porphyrins Immobilized on Mesoporous MCM-41 in Oxidation of Sulfides

Rayati¹,

Ruzbahani²,

Nejabat³

2017

MHC

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“…The so-called "ship-in-a-bottle" approach was widely explored but seldom applied to the oxidation of cyclohexane, or to the use of air as the oxidant; these prior studies used primarily tert-butyl hydroperoxide (TBHP) or similar oxidants as well as solvents [5][6][7][8]. Multiple studies of porphyrin or other macrocyclic ligand based transition metal complexes enmeshed in a zeolite cage, inorganic mimics of the naturally occurring cytochrome P450 enzyme, have also focused on the use of H 2 O 2 or TBHP as oxidants for a wide variety of oxidations, including that of cyclohexane [9]. We report the results of a broad study of heterogeneous zeolite-based catalysts for the oxidation of cyclohexane under mild conditions with unexpected results.…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Cyclohexane by Transition Metal Oxides on Zeolites

Riley¹

2012

TOCATJ

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Transition metals (Co, Mn, Fe, and Cu) were deposited as the hydrated oxides on a series of zeolites (Y, , ZSM-5, mordenite, and ferrierite) and examined for activity for the oxidation of cyclohexane at 70°C and ambient pressure. The materials that demonstrated catalytic activity under these extremely mild conditions were the cobalt-based catalysts. The copper and copper/iron materials demonstrated stoichiometric activity for the oxidation of cyclohexane to cyclohexanol and cyclohexanone. The cobalt-based catalysts produced the intriguing products caprolactone, 1-hexanol, and 3-methyl-1-pentanol, as well as the expected cyclohexanol and cyclohexanone. Of most interest was the production of 1-hexanol, indicative of novel activity in the oxidative ring cleavage and oxidation of cyclohexane.

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“…deactivation by irreversible dimerization, oxidative self-destruction of metalloporphyrins, and so forth, researcher immobilize MPs onto various supports, such as polymer, silica or hybrid materials [6][7][8][9][10]. Among these supports, polymer supports [11][12][13][14] have attracted much attention due to their several advantages, which are in some respects analogous to the influence of the polypeptide chain in hemoproteins: they protect MPs and improve the catalytic performances. Besides, the nitrogenous axial ligands could assist MPs on the catalysis.…”

Section: Introductionmentioning

confidence: 99%

The catalytic activity of poly(N-vinylimidazole)/SiO2-supported metalloporphyrins in ethyl benzene oxidation

Wang

Zhu

Gao

2011

Reac Kinet Mech Cat

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In this paper, novel kind of supports for immobilizing metalloporphyrin catalysts, poly(N-vinylimidazole)/SiO 2 (PVI/SiO 2 ) were prepared in the manner of ''grafting from''. Then, various metalloporphyrins (MPs), such as cobalt, iron and manganese tetraphenylporphyrins (CoTPP, FeTPP, MnTPP), cobalt tetra (paranitrophenyl) porphyrin (CoTNPP), and cobalt tetra (para-chlorophenyl) porphyrin (CoTClPP), were immobilized on the supports PVI/SiO 2 via the axial coordination reaction between MPs and the imidazole groups of the grafted PVI, resulting in the heterogenized catalysts MPs-PVI/SiO 2 . The supported catalysts were characterized by IR and UV-Vis spectra. The catalytic performances of MPs-PVI/SiO 2 for the oxidation of ethyl benzene in the absence of any reductant and solvent were investigated and compared in detail. The experimental results revealed that MPs-PVI/SiO 2 could effectively activate dioxygen, and obviously catalyze the oxidation of ethyl benzene to acetophenone. The catalytic activities of MPs-PVI/SiO 2 increased with increase of the electron-deficient degree of the peripheral substituent attached to the benzene ring outside the porphyrin ring. The catalytic activities of MPs-PVI/SiO 2 differed among the different metals and the different substitutional groups according to the following sequences: Co(II) [ Fe(III) [ Mn(III), and CoTNPP [ CoTClPP [ CoTPP. In comparison, the catalytic activity of CoTNPP-PVI/SiO 2 was the best. Under the reaction conditions of 120°C and the ordinary pressure of oxygen, the catalyst CoTNPP-PVI/SiO 2 gave wonderful results with 33.4 mol% yield of acetophenone.

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Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide

Cited by 75 publications

References 30 publications

A Comparative Study of Catalytic Activity of Fe, Mn and Cu Porphyrins Immobilized on Mesoporous MCM-41 in Oxidation of Sulfides

A Comparative Study of Catalytic Activity of Fe, Mn and Cu Porphyrins Immobilized on Mesoporous MCM-41 in Oxidation of Sulfides

Oxidation of Cyclohexane by Transition Metal Oxides on Zeolites

The catalytic activity of poly(N-vinylimidazole)/SiO2-supported metalloporphyrins in ethyl benzene oxidation

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