Electrochemical Oxidation of Benzene to Phenol

Lee, Byungik; Naito, Hiroto; Hibino, Takashi

doi:10.1002/anie.201105229

Cited by 54 publications

(36 citation statements)

References 29 publications

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“…Alternatively, it can be produced by water oxidation at the anode of an electrochemical cell. It was shown recently that benzene is oxidized at a VO x anode under a potential around +1000 mV in a gas atmosphere of 5 vol % benzene and 1 vol % H 2 O in argon with a remarkable current efficiency of 76 % and selectivity towards phenol of 95 % at 400 °C 224…”

Section: Oxidation Of Ch Bonds In Aromatic Compoundsmentioning

confidence: 99%

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

et al. 2012

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Although catalytic reductions, cross‐couplings, metathesis, and oxidation of CC double bonds are well established, the corresponding catalytic hydroxylations of CH bonds in alkanes, arenes, or benzylic (allylic) positions, particularly with O2, the cheapest, “greenest”, and most abundant oxidant, are severely lacking. Certainly, some promising examples in homogenous and heterogenous catalysis exist, as well as enzymes that can perform catalytic aerobic oxidations on various substrates, but these have never achieved an industrial‐scale, owing to a low space‐time‐yield and poor stability. This review illustrates recent advances in aerobic oxidation catalysis by discussing selected examples, and aims to stimulate further exciting work in this area. Theoretical work on catalyst precursors, resting states, and elementary steps, as well as model reactions complemented by spectroscopic studies provide detailed insight into the molecular mechanisms of oxidation catalyses and pave the way for preparative applications. However, O2 also poses a safety hazard, especially when used for large scale reactions, therefore sophisticated methodologies have been developed to minimize these risks and to allow convenient transfer onto industrial scale.

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Section: Oxidation Of Ch Bonds In Aromatic Compoundsmentioning

confidence: 99%

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

et al. 2012

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“…Similar to the Fenton system, electro‐Fenton reagents,, in which either Fe 2+ or H 2 O 2 is continuously electro‐generated in the reaction medium under direct electrochemical– and photoelectrochemical conditions, have been reported. Apart from that, heterogeneous catalytic reaction systems in the presence of a co‐oxidant (O 2 , H 2 O 2 ), such as a copper zeolite, heteropolyacid, and Pd(OAc), immobilized hexagonal mesoporous silica and polyimine, V 2 O 5 , chloro triphosphazenyl‐anchored mesoporous silica, CuCr 2 O 4 , carbon nanotubes, or second‐generation Fenton reagents, in which iron ions or iron‐based compounds immobilized ex situ on the electrode surface, for instance, Fe‐PbO 2 /Ti anodes, Fe 3 O 4 /CMK‐3, and iron electrodes reacted with H 2 O 2 have also been reported in the literature. Note that most of the above‐mentioned oxidation procedures involve either harsh chemical conditions,,, or elevated reaction temperatures ( T =50–250 °C) ,,–.…”

Section: Introductionmentioning

confidence: 99%

Intrinsic Iron‐Containing Multiwalled Carbon Nanotubes as Electro‐Fenton Catalyst for the Conversion of Benzene to Redox‐Active Surface‐Confined Quinones

Vishnu

Kumar

2016

ChemElectroChem

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Multiwalled carbon nanotubes containing an iron impurity (2.1 wt %) (MWCNT‐Fe*) were used to modify a glassy carbon electrode (GCE/MWCNT‐Fe*), which was subsequently exploited for the electrochemical oxidation of benzene (BZ) to redox‐active and surface‐confined quinones (BZO) in H2O2 containing pH 2 HCl–KCl. Physicochemical and electrochemical characterization methods, such as transmission electron microscopy, Raman spectroscopy, Fourier transform infrared spectroscopy, UV/Vis spectroscopy, liquid chromatography coupled mass spectroscopy, and cyclic voltammetry studies with naked Fe3+/2+, catechol (CA), and hydroquinone (HQ), evidenced that, in the presence of H2O2, the intrinsic iron impurity in MWCNT‐Fe* follows the electro‐Fenton reaction to oxidize BZ to BZO (CA+HQ) on the surface of MWCNT‐Fe* (i.e. GCE/MWCNT‐Fe*@BZO). Electro‐catalytic oxidation of hydrazine was demonstrated as a model system for the application of the GCE/MWCNT‐Fe*@BZO catalyst.

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“…Phenols are important organic chemical raw materials that have been produced by multistep reactions with high power consumption for several decades. Recently, the one‐step catalytic synthesis of phenols has attracted considerable interest in terms of atom efficiency and environmental friendliness. The key technique for the direct synthesis of phenols lies in the design and synthesis of efficient catalysts.…”

Section: Introductionmentioning

confidence: 99%

Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H₂O₂

Wang

Zhang

et al. 2014

Applied Organom Chemis

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A mononuclear iron(II) complex, Et 4 N[Fe(C 10 H 6 NO 2 ) 3 ], coordinated by three 1-nitroso-2-naphtholate ligands in a fac-N 3 O 3 geometry, was initiated to catalyze the direct hydroxylation of aromatic compounds to phenols in the presence of H 2 O 2 under mild conditions. Various reaction parameters, including the catalyst dosage, temperature, mole ratio of H 2 O 2 to benzene, reaction time and solvents which could affect the hydroxylation activity of the catalyst, were investigated systematically for benzene hydroxylation to obtain ideal benzene conversion and high phenol distribution. Under the optimum conditions, the benzene conversion was 10.2% and only phenol was detected. The catalyst was also found to be active towards hydroxylation of other aromatic compounds with high substrate conversions. The hydroxyl radical formed due to the reaction of the catalyst and H 2 O 2 was determined to be the crucial active intermediate in the hydroxylation. A rational pathway for the formation of the hydroxyl radical was proposed and justified by the density functional theory calculations.

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Electrochemical Oxidation of Benzene to Phenol

Cited by 54 publications

References 29 publications

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

Intrinsic Iron‐Containing Multiwalled Carbon Nanotubes as Electro‐Fenton Catalyst for the Conversion of Benzene to Redox‐Active Surface‐Confined Quinones

Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H₂O₂

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Electrochemical Oxidation of Benzene to Phenol

Cited by 54 publications

References 29 publications

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

Selective Catalytic Oxidation of CH Bonds with Molecular Oxygen

Intrinsic Iron‐Containing Multiwalled Carbon Nanotubes as Electro‐Fenton Catalyst for the Conversion of Benzene to Redox‐Active Surface‐Confined Quinones

Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H2O2

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Efficient hydroxylation of aromatic compounds catalyzed by an iron(II) complex with H₂O₂