Novel Catalysts for Olefin Cleavage Using Hydrogen Peroxide

Johnstone, Andrew N.C.; Middleton, Patrick J.; Sanderson, William R.; Harrison, Paul R.

doi:10.1016/s0167-2991(08)63454-0

Cited by 7 publications

(2 citation statements)

References 6 publications

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“…The combination of MoO 3 /RuCl 3 with an ammonium phase transfer catalyst proved to be a catalytically active precursor in the cleavage of OA with H 2 O 2 under acidic conditions. Hundred percent conversion of OA and yield of AA were observed, but due to the catalase activity of Ru a 7-8 fold molar excess of H 2 O 2 had to be added [72]. About 50% of H 2 O 2 decomposed unutilized, which makes the method inefficient from the economical point of view.…”

Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

114

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“…The second step of the reaction, that is, the oxidative cleavage of the diol primarily obtained promoted by the presence of both Co(Ac) 2 and H 2 WO 4 , has not been reported in any scientific paper but only in the patent literature . Some papers , reported the oxidative cleavage of the double bond with H 2 O 2 in the presence of tungstic and molibdic compounds, as catalysts, but using a phase-transfer agent. Therefore, our paper is mainly devoted to the study of the second step reaction, which is less well-known, with the aim (i) to find the best operative conditions, (ii) to improve yields and selectivities, (iii) to understand the catalytic mechanism, and (iv) to recover efficiently the products from the reaction mixtures.…”

Section: Introductionmentioning

confidence: 99%

Oxidative Cleavage of the Double Bond of Monoenic Fatty Chains in Two Steps: A New Promising Route to Azelaic Acid and Other Industrial Products

Santacesaria

Sorrentino

Rainone

et al. 2000

Ind. Eng. Chem. Res.

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We describe a process for the production of azelaic and pelargonic acids and ω-hydroxynonanoic and pelargonic acids by oxidative cleavage of the double bond of respectively oleic acid and oleyl alcohol in two reaction steps. In the first step the monoenic reagents react with hydrogen peroxide in the presence of pertungstic acid, as the catalyst, giving a diol, as the reaction product, that can be easily separated and purified. The key factors influencing this reaction have been studied. The second step is the oxidative cleavage with molecular oxygen of the diol formed in the first step, in the presence of catalyst formed in situ from tungstic acid and cobalt acetate. The nature of the catalyst, probably a poly(oxametalate), has been studied; factors affecting conversion and yields have been examined and the possible mechanisms discussed.

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Selective Oxidation – Homogeneous

Sheldon

Brink

Arends

2002

Encyclopedia of Catalysis

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In the manufacture of fine chemicals there is a considerable pressure to replace traditional oxidation techniques, using stoichiometric quantities of high valent metal salts, with cleaner, catalytic alternatives. This article focuses on homogeneous catalysis of liquid‐phase oxidations employing dioxygen, hydrogen peroxide, or alkyl hydroperoxides as the primary oxidant. Where relevant, heterogeneous equivalents are also discussed. Following a general introduction, which includes a discussion of the different reaction mechanisms and of the design of ligands for oxidation catalysts, the different classes of substrates are discussed. These are alkenes (epoxidation, vicinal dihydroxylation, oxidative cleavage, ketonization, and allylic oxidation), alkanes and alkyl aromatics (side‐chain versus aromatic‐ring oxidation), oxygen‐containing compounds (alcohols, diols, aldehydes, ketones, phenols, and ethers), amines, and sulfur‐containing compounds. A separate section is devoted to asymmetric catalysis (epoxidation and dihydroxylation of olefins, sulfoxidation, and Baeyer–Villiger oxidation).

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Novel Catalysts for Olefin Cleavage Using Hydrogen Peroxide

Cited by 7 publications

References 6 publications

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Oxidative Cleavage of the Double Bond of Monoenic Fatty Chains in Two Steps: A New Promising Route to Azelaic Acid and Other Industrial Products

Selective Oxidation – Homogeneous

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