Liquid-phase oxidation of benzene to phenol by CuO–Al 2 O 3 catalysts prepared by co-precipitation method

Miyahara, Takahiro; Kanzaki, Hiroshi; Hamada, Rei; Kuroiwa, Satoshi; Nishiyama, Satoru; Tsuruya, Shigeru

doi:10.1016/s1381-1169(01)00242-4

Cited by 103 publications

(72 citation statements)

References 14 publications

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“…In several other studies, iron was replaced by other redox metals. Thus, studies have been performed in the presence of Cu-supported zeolites, [22] Cu-supported MCM-41 catalysts, [23] and CuOAl 2 O 3 [24] but yields obtained were still lower than 1%. Higher yields of phenol are also reported when iron is replaced by vanadium catalysts.…”

Section: Direct Hydroxylation Of Aromatic Compoundsmentioning

confidence: 99%

Oxidation and Ammoxidation of Aromatics

Lücke¹,

Narayana²,

Martin³

et al. 2004

Adv Synth Catal

130

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An overview of the state of the art in the direct oxygen or nitrogen insertion to aromatic rings and side-chains by hydroxylation, acetoxylation, partial oxidation and ammoxidation is presented. The influence of a variety of catalysts and oxidants on the yields of hydroxylated products of aromatic species is discussed in more detail. The survey is also focussed on the usage of H 2 O 2 as an effective oxidising agent for hydroxylation reactions. Acetoxylation of methyl-substituted aromatic compounds to their corresponding esters in a single step is indeed an interesting area from an industrial point of view. Hence, the topics covering benzylic acetoxylation, although they are under a developmental stage for commercial exploitation, are also reviewed. The present contribution also covers the main directions of selective oxidation/ammoxidation of aromatic compounds to useful products, surveys recent developments and provides an updated discussion of the state of the art in the field of oxidation and ammoxidation of aromatics. Additionally, a comparative study of the vapour phase oxidation and ammoxidation of different alkyl aromatics to their corresponding aldehydes and nitriles using various heterogeneous catalysts is presented.Besides, the achievements and limitations of the catalysts/processes are emphasised. Furthermore, the present article includes a discussion of common features and differences in mechanistic steps of oxidation and ammoxidation reactions investigated by in situ FITR spectroscopy. The influence of acid-base properties of catalyst surfaces in connection with electronic effects of the substituents on the performance of the catalysts is also described.

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Section: Direct Hydroxylation Of Aromatic Compoundsmentioning

confidence: 99%

Oxidation and Ammoxidation of Aromatics

Lücke¹,

Narayana²,

Martin³

et al. 2004

Adv Synth Catal

130

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“…148,149 A Cu/ ZSHM-5 catalyst showed a maximum phenol selectivity of 60% with a phenol yield of 1.2% at 673 K. 150 However, the selective oxidation of benzene using O 2 was nominated as one of the ten most difficult challenges in catalysis 177179 and indeed there have been no reports on direct remarkable catalysts for phenol synthesis with performance greater than 5% benzene conversion and 50% phenol selectivity over the last 50 years.…”

Section: Tadamentioning

confidence: 99%

Surface-Mediated Design and Catalytic Properties of Active Metal Complexes for Advanced Catalysis Creation

Tada¹

2010

Bulletin of the Chemical Society of Japan

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Molecular-scale design of catalytically active structures at oxide surfaces is highlighted, focusing on our recent challenges for selective heterogeneous catalysis. We found novel structural transformations of supported metal complexes on oxide surfaces and achieved unique selective catalysis for various chemical syntheses. In this account, the advanced design of supported metal-complex catalysts on oxide surfaces and the in situ characterization of their structural kinetics, which means kinetics of structural changes of catalysts themselves, under catalyst-working conditions are reviewed. Surface-Mediated Design of Catalytically ActiveStructures for Selective Catalysis 1.1 Introduction: Metal-Complex Attaching on Oxide Surfaces. Heterogeneous solid catalysts have been widely utilized for the industrial production of many synthetic chemicals. The advantages of heterogeneous catalysts are not only the separation of catalysts and products from reaction media but also their high durability and catalytic activities resulting from the unique structures of catalytically active sites at solid surfaces. Relationships among the metal structures, organized environment, and the catalytic properties of surface species tell us the nature of catalysis and new strategy for rational design of heterogeneous catalysts.Metal-complex attachment to oxide surfaces is a practical way to produce molecularly regulated structures of active metal species on oxide surfaces, and subsequent structural transformation in a controllable manner often provides unique regulated metal structures active for selective catalytic reactions. 116 There are several types of metal-complex attachment techniques: coordination of metal-complex precursors to immobilized ligands on organic polymers, 1721 coordination of metal-complex precursors to functional ligands bound to oxide surfaces, 2,4,2225 intercalation into clay materials, 26 ion exchange into porous materials such as zeolite and mesoporous silica, 27 and direct attachment of metal-complex precursor onto oxide surfaces. 3,6,11,28,29 The interfacial attachment between a metal complex and an oxide surface can produce unique metal coordination different from the original metal-complex precursor. For example, SiOH is reacted with a M(CH 3 ) complex and a M(OSi) complex is produced, releasing CH 4 . A chemical bond between a metal-complex precursor and a support surface modifies the reactivity of the supported metal complex, resulting in novel catalytic activity the precursor complex does not exhibit. 3,6,11,28,29 Traditional ion-exchange on zeolites and intercalation to clay materials are also typical ways to introduce metal species onto solid supports although the valences and types of metal precursors are restricted. 4 Direct reactions of metal-complex precursors and hydroxy groups on oxide surfaces create novel metal-coordination structures, and many important factors for selective catalysis can be controlled at the interface, such as electronic properties and coordination sphere of the attached metal...

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“…Many tion of benzene to phenol in the biphasic benzene-water catalysts such as Cu 1) , V 2), 3) , Pd 4), 5) and Pt 5) have been system by incorporating a regenerator into the reactorinvestigated for direct oxidation with molecular oxygen. extractor system.…”

Section: Introductionmentioning

confidence: 99%

Catalyst Regenerator for Partial Oxidation of Benzene in Reaction-extraction System

Yamada

Mizuno

Tagawa

et al. 2008

J. Jpn. Petrol. Inst.

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The liquid-phase oxidation of benzene to phenol was investigated in the biphasic benzene-water system using VCl3 and molecular oxygen as the catalyst and oxidant, respectively. Benzene was dissolved in the aqueous catalyst phase and reacted with oxygen to form phenol. Phenol was preferentially extracted into the benzene phase, thus suppressing the formation of over-oxidized byproducts. During the reaction, the catalyst was oxidized and deactivated. To regenerate the catalyst, a regenerator was installed into the system. Hydrogen was fed to the regenerator to reduce the deactivated catalyst, but no significant improvement of the system performance was observed without the presence of a second catalyst. Pd sheet in the regenerator allowed the system to run very stably, and the system was easy to shut down and start up.

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Liquid-phase oxidation of benzene to phenol by CuO–Al 2 O 3 catalysts prepared by co-precipitation method

Cited by 103 publications

References 14 publications

Oxidation and Ammoxidation of Aromatics

Oxidation and Ammoxidation of Aromatics

Surface-Mediated Design and Catalytic Properties of Active Metal Complexes for Advanced Catalysis Creation

Catalyst Regenerator for Partial Oxidation of Benzene in Reaction-extraction System

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