New Ways in the Catalytic Epoxidation of Olefins by Hydrogen Peroxide

Pralus, Magali; Lecoq, Jonathan; Schirmann, Jean-Pierre

doi:10.1007/978-1-4613-2958-9_22

Cited by 14 publications

(3 citation statements)

References 2 publications

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“…This can be achieved only by means of suitable catalysts which are based mainly on group 5A,B and 6A,B metal oxides.1,2 To date, however, valuable results in the case of simple, monosubstituted olefins have been obtained only by working under virtually anhydrous conditions. 3,4 We now have found that the two-component association consisting of tungstate and phosphate (or arsenate) ions, under acidic conditions, represents a valuable catalytic…”

Section: Methodsmentioning

confidence: 99%

High pressure [4 + 2] cycloaddition of dichloromaleic anhydride and furan

Okamoto¹,

Giandinoto²,

Bochnik³

1983

J. Org. Chem.

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methylpropyl)benzene. By a combination of peak intensities, sford, previously related assignments,14 and the data for the 1.1-diphenyl-2,2-dimethylpropane above it was possible to assign each line in this spectrum as follows: (1) For the 1,1-diphenyl-2.2-dimethylpropyl group, 64.8 (C-l), 39.6 (C-2), 32.5 (CH3), phenyl 147.2 (C-l), 126.9 (C-2,6), 131.4 (C-3,5), and 125.7 (C-4); (2) For the l-phenyl-2,2-dimethylpropyl group, 63.8 (C-l), 35.1 (C-2), 29.2 (CH3), phenyl 143.2 (C-l), 129.9 (C-2,6), 127.8 (C-3,5), and 126.0 (C-4); and finally for the benzene moiety, 140.4 (C-l), 128.4 (C-2,6), 130.9 (C-3,5), and 144.5 ppm (C-4).Acknowledgment. Grateful acknowledgment is hereby extended to The Robert A. Welch Foundation for their support of this work.Registry No. l,l-Diphenyl-2,2-dimethylpropyl radical, 51974-45-9; l,l-diphenyl-2,2-dimethylpropane, 38842-11-4; 1,1diphenyl-2,2-dimethylpropyl dimer, 86943-05-7; 4-(l,1-diphenyl-2,2-dimethylpropyl)-l-(l-phenyl-2,2-dimethylpropyl)benzene, 86943-06-8.

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Section: Methodsmentioning

confidence: 99%

High pressure [4 + 2] cycloaddition of dichloromaleic anhydride and furan

Okamoto¹,

Giandinoto²,

Bochnik³

1983

J. Org. Chem.

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“…Although it is also possible to use other catalysts, such as molybdenum oxide or tungsten oxide, to epoxidize propene with hydrogen peroxide, these catalysts are all extremely sensitive to the presence of water. , Homogeneous catalysts are not preferred, because of additional separation costs.…”

Section: Current Processesmentioning

confidence: 99%

The Production of Propene Oxide: Catalytic Processes and Recent Developments

Nijhuis

Makkee

Moulijn

et al. 2006

Ind. Eng. Chem. Res.

484

405

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Propene oxide, which is one of the major commodity chemicals used in chemical industry, desperately requires a new process for its production, because of the disadvantages that are encountered with the currently available processes. This paper discusses the existing processes used for the production of propene oxidesthe chlorohydrin and hydroperoxide processessand their advantages and disadvantages. Furthermore, the new processes and catalysts under development for the propene oxide production are discussed, as well as the challenges that are still limiting the applications of some of those prospects. The most important new developments for the production of propene oxide discussed in this paper are: the hydrogen peroxide combination process, the ethene oxide alike silver catalysts, the molten salt systems, and the gold-titania catalyst systems.

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“…The Pd catalysts employed for the direct route also catalyze the decomposition of H 2 O 2 in water, and hence, a number of patents disclose means of stabilizing the aqueous H 2 O 2 , although there is little discussion of the ultimate fate of these stabilizers . New catalysts and catalyst supports are often described, and recently, catalytic membranes have also been introduced…”

Section: Direct Generation Of H2o2 From H2 and O2mentioning

confidence: 99%

H₂O₂ in CO₂/H₂O Biphasic Systems: Green Synthesis and Epoxidation Reactions

Hâncu

Green

Beckman

2002

Ind. Eng. Chem. Res.

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Hydrogen peroxide is a "green" oxidant whose relatively high cost has prevented it from being generally applied to commodity chemical processing. In large part, the attributes of the current H 2 O 2 process (the anthraquinone, or AQ, route) that contribute to its high cost also contribute to its nonsustainable features: byproduct streams, high energy input and solvent usage, and multiple required unit operations. We have explored the generation of hydrogen peroxide directly from hydrogen and oxygen using liquid CO 2 as the solvent. Producing H 2 O 2 directly from H 2 and O 2 in the presence of a CO 2 -soluble Pd catalyst could potentially eliminate entire unit operations and reduce raw material costs significantly. Further, homogeneous reaction in liquid CO 2 allows for contact between significant concentrations of O 2 and H 2 , high rates of reaction, and ready recovery of the product via stripping into water. Both Pd(+2) and Pd(0) catalysts were explored for the reaction; our results suggest that future work should focus on the optimization of a CO 2 -soluble or -dispersible Pd(0) catalyst. Finally, we have found that CO 2 / H 2 O 2 /H 2 O mixtures are, themselves, useful reagent systems. A biphasic aqueous H 2 O 2 /CO 2 mixture is an efficient epoxidizing system, where HCO 4is formed through various reactions of water, CO 2 , and H 2 O 2 and transfers of oxygen to alkenes. From our results, it appears that H 2 O 2 can react directly with CO 2 , producing more percarbonate ion than in situations that employ only bicarbonate as the precursor.

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New Ways in the Catalytic Epoxidation of Olefins by Hydrogen Peroxide

Cited by 14 publications

References 2 publications

High pressure [4 + 2] cycloaddition of dichloromaleic anhydride and furan

High pressure [4 + 2] cycloaddition of dichloromaleic anhydride and furan

The Production of Propene Oxide: Catalytic Processes and Recent Developments

H₂O₂ in CO₂/H₂O Biphasic Systems: Green Synthesis and Epoxidation Reactions

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New Ways in the Catalytic Epoxidation of Olefins by Hydrogen Peroxide

Cited by 14 publications

References 2 publications

High pressure [4 + 2] cycloaddition of dichloromaleic anhydride and furan

High pressure [4 + 2] cycloaddition of dichloromaleic anhydride and furan

The Production of Propene Oxide: Catalytic Processes and Recent Developments

H2O2 in CO2/H2O Biphasic Systems: Green Synthesis and Epoxidation Reactions

Contact Info

Product

Resources

About

H₂O₂ in CO₂/H₂O Biphasic Systems: Green Synthesis and Epoxidation Reactions