Synthesis of adipic acid catalyzed by surfactant-type peroxotungstates and peroxomolybdates

Zhu, Wenshuai; Li, Huaming; He, Xiaoxiao; Zhang, Qi; Shu, Huoming; Yan, Yongsheng

doi:10.1016/j.catcom.2007.07.038

Cited by 73 publications

(38 citation statements)

References 27 publications

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“…The long carbon chain cation possesses lipophilic nature, which plays an important role in transferring the active oxygen from the aqueous to the organic phase. The structure and composition of tungstate species with the presence of H 2 O 2 in our former work have been studied by Raman spectroscopy [16,17]. Therefore, a possible catalytic cycle is given in Scheme 2 for the biphasic oxidation in the emulsion system.…”

Section: Investigation Of Total Sulfur Content In Real Dieselmentioning

confidence: 99%

Deep oxidative desulfurization of fuels catalyzed by pristine simple tungstic acid

Zhu

Lü

et al. 2009

React Kinet Catal Lett

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The catalytic system of pristine simple tungstic acid and quaternary ammonium salts has been found suitable for deep removal of sulfur in diesel with H 2 O 2 as oxidant. The longer the length of the carbon chain of the quaternary ammonium salt is, the better its catalytic activity is in desulfurization. By combining oxidation and extraction with dimethylformamide, low sulfur level in diesel could be obtained.

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Section: Investigation Of Total Sulfur Content In Real Dieselmentioning

confidence: 99%

Deep oxidative desulfurization of fuels catalyzed by pristine simple tungstic acid

Zhu

Lü

et al. 2009

React Kinet Catal Lett

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“…In addition to the aforementioned studies, Zhu et al also proposed a possible catalytic mechanism for biphasic oxidation in emulsion by relying on a complete collection of Raman spectra of tungsten and molybdenum peroxo species. [38] The authors suggested a possible conversion of the dimeric Q 2 The versatility and ease of the assembly between cationic surfactants and anionic catalysts to generate tunable processes have resulted in outstanding developments in oxidation/epoxidation reactions, allowing easy product separation and catalyst recovery. [38,39] The second strategy relies on the synthesis of organicinorganic hybrid amphiphilic surfactants where the POM acts as a polar head group.…”

Section: Amphiphilic Oxidation Catalystsmentioning

confidence: 99%

“…[38] The authors suggested a possible conversion of the dimeric Q 2 The versatility and ease of the assembly between cationic surfactants and anionic catalysts to generate tunable processes have resulted in outstanding developments in oxidation/epoxidation reactions, allowing easy product separation and catalyst recovery. [38,39] The second strategy relies on the synthesis of organicinorganic hybrid amphiphilic surfactants where the POM acts as a polar head group. By using such an approach, Liu et al grafted hexavanadate POM anions with long-chain alkyl tails to obtain POM-organic compounds to afford w/o emulsions (SIC system).…”

Section: Amphiphilic Oxidation Catalystsmentioning

confidence: 99%

Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

Leclercq²,

et al. 2015

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Pickering emulsions are surfactant-free dispersions of two immiscible fluids that are kinetically stabilized by colloidal particles. For ecological reasons, these systems have undergone a resurgence of interest to mitigate the use of synthetic surfactants and solvents. Moreover, the use of colloidal particles as stabilizers provides emulsions with original properties compared to surfactant-stabilized emulsions, microemulsions, and micellar systems. Despite these specific advantages, the application of Pickering emulsions to catalysis has been rarely explored. This Minireview describes very recent examples of hybrid and composite amphiphilic materials for the design of interfacial catalysts in Pickering emulsions with special emphasis on their assets and challenges for industrially relevant biphasic reactions in fine chemistry, biofuel upgrading, and depollution.

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“…Other papers have examined the use of either surfactant‐type polyoxometalates or amphiphilic, quaternary ammonium salts of tungstophosphates (precursors for the corresponding peroxometalates after contacting with HP) for the oxidative cleavage of vicinal diols to carboxylic acids; AA yields higher than 90 % in CHD hydroperoxidation have been reported 13–16. Ti‐containing sandwich‐type As/W polyoxometalates, too, are catalysts for the oxidation and oxidative cleavage of cyclohexene into the epoxide, CHD, 2‐hydroxycyclohexanone, 6‐hydroxycaprolactone, adipic aldehyde, and AA 17…”

Section: Introductionmentioning

confidence: 99%

Oxidation of 1,2‐Cyclohexanediol to Adipic Acid with Oxygen: A Study Into Selectivity‐Affecting Parameters

Rozhko¹,

Raabová²,

Macchia³

et al. 2013

ChemCatChem

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The aerobic oxidation of trans‐1,2‐cyclohexanediol in the synthesis of adipic acid was studied. Two classes of catalysts are compared, 1) alumina‐supported Ru(OH)3, and 2) Keggin type P/Mo/V polyoxometalates. These two classes are representative examples because they are active in alcohol oxidation under quite different reaction conditions. In the former case, basic conditions are needed in order to activate the substrate, whereas with polyoxometalates, acidic conditions are used. Their catalytic behavior showed remarkable differences; in basic conditions, the reaction network was very complex, and several side reactions led to a number of by‐products, with a low selectivity to adipic acid in the end. The supported Ru(OH)3 catalyst was very efficient in 1,2‐cyclohexanediol oxidative dehydrogenation to 1,2‐cyclohexanedione, but several undesired reactions occurred starting from this key intermediate under basic conditions: rearrangement into 6‐hydroxycaprolactone and 1‐hydroxycyclopentanecarboxylic acid, and formation of the product of aldol condensation. The former compound was also an intermediate for adipic acid formation, but this reaction gave only a minor contribution to the reactant conversion. Polyoxometalates were extremely selective in 1,2‐cyclohexanediol conversion into adipic acid, but under acidic conditions the product reacted with the unconverted reactant to yield the corresponding ester.

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Synthesis of adipic acid catalyzed by surfactant-type peroxotungstates and peroxomolybdates

Cited by 73 publications

References 27 publications

Deep oxidative desulfurization of fuels catalyzed by pristine simple tungstic acid

Deep oxidative desulfurization of fuels catalyzed by pristine simple tungstic acid

Pickering Interfacial Catalysis for Biphasic Systems: From Emulsion Design to Green Reactions

Oxidation of 1,2‐Cyclohexanediol to Adipic Acid with Oxygen: A Study Into Selectivity‐Affecting Parameters

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