Oxo-vanadium (IV) phthalocyanine implanted onto the modified SBA-15 as a catalyst for direct hydroxylation of benzene to phenol in acetonitrile-water medium: A kinetic study

Farahmand, Shohreh; Ghiaci, Mehran; Asghari, Saeid

doi:10.1016/j.ces.2020.116331

Cited by 22 publications

(11 citation statements)

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“…Therefore, the search for new applications of these V-containing petroporphyrins is highly interesting. Vanadium(IV)-porphyrin-containing materials are also paramount [ 24 , 25 , 26 , 27 ], in which special attention has been paid to the use of Vanadyl-porphyrins incorporated on the surface of supports or encapsulated in mesoporous materials [ 13 , 28 , 29 , 30 , 31 , 32 ]. It is well-known that changes in the type of functional groups and/or in the position of the substituents in the porphyrin macrocycle can give rise to modifications in the physicochemical and catalytic properties [ 6 , 7 , 8 , 9 ], but significant changes in physicochemical characteristics could also occur when incorporating metalloporphyrins into inorganic oxides [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 28 , 29 , 30 , 31 , 32 ].…”

Section: Introductionmentioning

confidence: 99%

V-Porphyrins Encapsulated or Supported on Siliceous Materials: Synthesis, Characterization, and Photoelectrochemical Properties

et al. 2022

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Metalloporphyrin-containing mesoporous materials, named VTPP@SBA, were prepared via a simple anchoring of vanadyl porphyrin (5,10,15,20-Tetraphenyl-21H,23H-porphine vanadium(IV) oxide) through a SBA-15-type mesoporous material. For comparison, vanadyl porphyrin was also impregnated on SiO2 (VTPP/SiO2). The characterization results of catalysts by XRD, FTIR, DR-UV-vis, and EPR confirm the incorporation of vanadyl porphyrin within the mesoporous SBA-15. These catalysts have also been studied using electrochemical and photoelectrochemical methods. Impedance measurements confirmed that supporting the porphyrin in silica improved the electrical conductivity of samples. In fact, when using mesoporous silica, current densities associated with oxidation/reduction processes appreciably increased, implying an enhancement in charge transfer processes and, therefore, in electrochemical performance. All samples presented n-type semiconductivity and provided an interesting photoelectrocatalytic response upon illumination, especially silica-supported porphyrins. This is the first time that V-porphyrin-derived materials have been tested for photoelectrochemical applications, showing good potential for this use.

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Section: Introductionmentioning

confidence: 99%

V-Porphyrins Encapsulated or Supported on Siliceous Materials: Synthesis, Characterization, and Photoelectrochemical Properties

et al. 2022

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“…Furthermore, the handling of the reaction byproducts, including acetone and α-methylstyrene, is problematic. In an alternative to the conventional cumene process, phenol can also be generated by activating the C–H bond of benzene with catalysts, such as palladium, supramolecular catalyst, metal/activated carbon catalyst, , or macromolecules such as oxo-vanadium(IV) phthalocyanine, combined with oxidants, such as N 2 O, O 2 , , and H 2 O 2 …”

Section: Introductionmentioning

confidence: 99%

“…2 Furthermore, the handling of the reaction byproducts, including acetone and α-methylstyrene, is problematic. In an alternative to the conventional cumene process, phenol can also be generated by activating the C−H bond of benzene with catalysts, such as palladium, 1 supramolecular catalyst, 2 metal/activated carbon catalyst, 3,4 or macromolecules such as oxo-vanadium(IV) phthalocyanine, 5 combined with oxidants, such as N 2 O, 6 O 2 , 1,7 and H 2 O 2 . 8 Recent reports have demonstrated that phenol can be generated in the gas phase upon the reaction between benzene and oxygen in N 2 /O 2 plasma produced either by atmospheric pressure corona discharge 9,10 or dielectric barrier discharge.…”

Section: ■ Introductionmentioning

confidence: 99%

Generation of Phenol and Molecular Hydrogen through Catalyst-Free C–H Activation of Benzene by Water Radical Cations

Mao

Wei

et al. 2021

J. Am. Soc. Mass Spectrom.

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Here, we report on the abundant formation of phenol and molecular hydrogen when benzene vapor was exposed to gas plasma generated by +5.5 kV corona discharge of water vapor in argon in the absence of oxygen. Systematic analysis using a series of isotopic standards (d 6-benzene, D2O, and H2 18O) and benzene derivatives (mono-, di-, trichlorobenzene, and N,N-dimethylaniline) indicated that the formation of phenol occurred through the reaction between neutral benzene and the radical cation of water dimer, (H2O)2 +•. A two-step reaction mechanism was proposed based on the results of experiments and DFT calculations: (1) the formation of (C6H6...H2O)+• intermediate through electrophilic addition; (2) the formation of C6H5OH+• through the release of H2 from the (C6H6...H2O)+• intermediate. Our findings offer a novel catalyst-free method to prepare phenol from benzene with phenol selectivity >90%.

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“…Vanadyl tetraaminophthalocyanine (TAVOP) was used in hydroxylation reaction of benzene [ 75 ]. The synthesized phthalocyanine was incorporated into mesopores of SBA-15 functionalized with CPTMS, which resulted in its covalent bonding, similarly iron(III) analogue, presented in Figure 2 f. The prepared complex TAVOPc@Cl-SBA was tested in benzene hydroxylation in the presence of O 2 , which led to phenol production.…”

Section: Porphyrins and Phthalocyanines Immobilized On Mesoporous Sil...mentioning

confidence: 99%

Porphyrins and Phthalocyanines on Solid-State Mesoporous Matrices as Catalysts in Oxidation Reactions

Szymczak

Kryjewski

2022

Materials

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The review presents recent examples of heterogenic catalysts based on porphyrins and phthalocyanines loaded on mesoporous materials, such as MCM-41, SBA-15, MCM-48, SBA-16 or Al-MCM-41. Heterogenic approach to catalysis eases recovery, reuse and prevent macrocycle aggregation. In this application, mesoporous silica is a promising candidate for anchoring macrocycle and obtaining a new catalyst. Introduction of porphyrin or phthalocyanine into the mesoporous material may be performed through adsorption of the macrocycle, or by its in situ formation—by reaction of substrates introduced to the pores of the catalytic material. Catalytic reactions studied are oxidation processes, focused on alkane, alkene or arene as substrates. The products obtained are usually epoxides, alcohols, ketones, aldehydes or acids. The greatest interest lies in oxidation of cyclohexane and cyclohexene, as a source of adypic acid and derivatives. Some of the reactions may be viewed as biomimetic processes, resembling processes that occur in vivo and are catalyzed by cytochrome P450 enzyme family.

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Oxo-vanadium (IV) phthalocyanine implanted onto the modified SBA-15 as a catalyst for direct hydroxylation of benzene to phenol in acetonitrile-water medium: A kinetic study

Cited by 22 publications

References 81 publications

V-Porphyrins Encapsulated or Supported on Siliceous Materials: Synthesis, Characterization, and Photoelectrochemical Properties

V-Porphyrins Encapsulated or Supported on Siliceous Materials: Synthesis, Characterization, and Photoelectrochemical Properties

Generation of Phenol and Molecular Hydrogen through Catalyst-Free C–H Activation of Benzene by Water Radical Cations

Porphyrins and Phthalocyanines on Solid-State Mesoporous Matrices as Catalysts in Oxidation Reactions

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