Indirect electrochemical epoxidation of hexene in a liquid-liquid electrolyte

Alkire, Richard C.; Köhler, Jürgen

doi:10.1007/bf01093755

Cited by 15 publications

(14 citation statements)

References 8 publications

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“…In all the epoxidations carried out the main by-products obtained were the corresponding bromohydrin (4 -23%) and dibromide (11% -20%) derivatives. In agreement with Alkire and Köhler [10] the bromohydrin precedes the formation of epoxide while dibromide formation prevents the formation of epoxide.…”

Section: -Enyl]benzenesupporting

confidence: 88%

“…Tori et al [9] reported that the electrooxidation of halide salts is useful for the generation of reactive species of halogen atoms under mild conditions. In fact, it has been shown that the Brion discharged from NaBr can be a good mediator for the epoxidation of dimethyl 4-cyclohexene-1,2-dicarboxylate and acyclic alkenes [9] and nhexene [10] in water-organic solvent media.…”

Section: Introductionmentioning

confidence: 99%

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Electroepoxidation of natural and synthetic alkenes mediated by sodium bromide

Inês

Mendonça

Esteves

et al. 2009

Comptes Rendus. Chimie

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Electroepoxidation of synthetic alkenes (styrene, trans-stilbene and trans-β-methylstyrene) and of some natural terpenes (limonene, terpinolene, geraniol, α-terpinene, γ-terpinene and   αterpineol) mediated by sodium bromide was performed in MeCN:H 2 O (4:1) at platinum electrodes. The indirect electrochemical oxidation of the olefins led to the corresponding epoxides in yields ranging from 23% to 79%. Résumé L'électroépoxydation d'alcènes synthétiques (styrène, trans-stilbène et trans-βméthylstyrène) et d'alcènes naturels terpéniques (limonène, terpinolène, géraniol, α-terpinène, γ-terpinène et α-terpinéol) à l'aide de bromure de sodium a été réalisée dans un mélange MeCN:H 2 O (4:1) avec des électrodes de platine. L'oxydation électrochimique indirecte d'oléfines conduit aux époxydes correspondants avec des rendements allant de 23% à 79%.

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Section: -Enyl]benzenesupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Electroepoxidation of natural and synthetic alkenes mediated by sodium bromide

Inês

Mendonça

Esteves

et al. 2009

Comptes Rendus. Chimie

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“…Recently, chloride-mediated electrosynthesis of ethylene oxide and propylene oxides from ethylene and propylene at high current density has been realized in a flow cell . Other redox mediators such as Br – /Br 2 and I – /I 2 were also developed for selective oxidation of various alkenes. − From the perspective of energy-saving, PEC synthesis is advantageous over electro-synthesis which requires high applied potentials and electric energy input. We envisioned that halide salt could be a competent redox mediator/catalyst in a PEC system to facilitate epoxide production when an appropriate photoanode was chosen.…”

Section: Introductionmentioning

confidence: 99%

Bromide-Mediated Photoelectrochemical Epoxidation of Alkenes Using Water as an Oxygen Source with Conversion Efficiency and Selectivity up to 100%

Liu

Chen

et al. 2022

J. Am. Chem. Soc.

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In a photoelectrochemical (PEC) cell, the production of solar fuels such as hydrogen is often accompanied either by the oxidation of water or by the oxidation of organic substrates. In this study, we report bromide-mediated PEC oxidation of alkenes at a mesoporous BiVO4 photoanode and simultaneous hydrogen evolution at the cathode using water as an oxygen source. NaBr as a redox mediator was demonstrated to play a dual role in the PEC organic synthesis, which facilitates the selective oxidation of alkenes into epoxides and suppresses the photocorrosion of BiVO4 in water. This method enables a near-quantitative yield and 100% selectivity for the conversion of water-soluble alkenes into their epoxides in H2O/CH3CN solution (v/v, 4/1) under simulated sunlight without the use of noble metal-containing catalysts or toxic oxidants. The maximum solar-to-electricity efficiency of 0.58% was obtained at 0.39 V vs Ag/AgCl. The obtained epoxide products such as glycidol are important building blocks of the chemical industry. Our results provide an energy-saving and environment-benign approach for producing value-added chemicals coupled with solar fuel generation.

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“…They react to provide industrially important products such as pharmaceuticals, surfactants, detergents, antistatic agents, corrosion protection agents, and additives for laundry detergents, lubricating oils, textiles and cosmetics 10. Few epoxidation processes are carried out in aqueous solution, and most of them need a catalyst and phase transfer agents11–15 or, alternatively, an electrochemical process 16. A method using aqueous potassium peroxymonosulfate (Oxone ® ) solution to oxidize alkenes into epoxides and diols without phase transfer catalyst was investigated by Zhu and Ford 17.…”

Section: Introductionmentioning

confidence: 99%

Two‐phase production of cyclohexene and cyclooctene oxides in water as an approach to pollution prevention

Shu

2004

J of Chemical Tech & Biotech

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Liquid-liquid two-phase epoxidation from cyclohexene and cyclooctene in aqueous potassium peroxymonosulfate (commercially available as Oxone  ) solution was studied as an application in pollution prevention. To avoid potential emissions of volatile organic compounds an aqueous solution was employed to replace the usual chlorinated solvents used in epoxide production. A droplet column reactor and stirred tank reactor were used to investigate two-phase synthesis of epoxide. An aqueous Oxone  solution was used to oxidize a dispersion of alkene droplets and form epoxide. The study of aqueous epoxidation in both reactors showed that the epoxidation of alkenes can be represented as a first order reaction with respect to alkene. The salting out effect of Oxone  concentration was studied in both reactors and found to be very similar at optimal conditions. In comparing the two reactors, it was found that the droplet column reactor produces larger quantities of product per unit reactor volume for the same reaction time. The objective of this study is to provide an alternative reactor design and synthesis route that can meet pollution prevention goals.

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Indirect electrochemical epoxidation of hexene in a liquid-liquid electrolyte

Cited by 15 publications

References 8 publications

Electroepoxidation of natural and synthetic alkenes mediated by sodium bromide

Electroepoxidation of natural and synthetic alkenes mediated by sodium bromide

Bromide-Mediated Photoelectrochemical Epoxidation of Alkenes Using Water as an Oxygen Source with Conversion Efficiency and Selectivity up to 100%

Two‐phase production of cyclohexene and cyclooctene oxides in water as an approach to pollution prevention

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