Reduction pathways of organohalogen compounds

Farwell, S. O.; Beland, Frederick A.; Geer, Richard D.

doi:10.1016/s0022-0728(75)80230-0

Cited by 70 publications

(22 citation statements)

References 16 publications

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“…[1][2][3] Figure 1 shows the reduction of hexachlorobenzene in acetonitrile at a glassy carbon electrode. Each peak indicates the loss of one chlorine.…”

Section: Resultsmentioning

confidence: 99%

“…This is because polychlorobiphenyls reduce at potentials that are at least 200 mV less negative than biphenyl. 27 Their rate of reaction is therefore expected to be faster or at least as fast as the rate of reduction of the isomers of dichlorobenzene which were also not detected by GC-MS analysis. It can thus be assumed that if tetrachlorobiphenyls are being generated, they should quickly be reduced to form eventually biphenyl or to undergo further radical-radical coupling.…”

Section: Mediated Electrolysis Of 124-trichlorobenzene-electrolysismentioning

confidence: 99%

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Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

Guena

Wang

Gattrell

et al. 2000

J. Electrochem. Soc.

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The use of a range of mediators for the partial or complete dechlorination of a series of polychlorinated benzenes has been investigated. The dechlorinations were carried out in acetonitrile, and the products were analyzed by gas chromatography-mass spectroscopy (GC-MS). The partial dechlorination using organic mediators was successful and good control of the reaction (i.e., monodechlorination) and good efficiency could be achieved. Some mediators showed poor current efficiencies due to the lower stability of their anion radical in the presence of protons. The monodechlorination of trichlorobenzene with four different mediators showed that the product distribution in terms of initial chlorine removed was little affected by the mediator used. This product distribution has also been investigated for the whole series of polychlorobenzenes. Polydechlorination using a single mediator was tried using biphenyl, anthracene, and dibenzofuran. After passing enough charge to completely dechlorinate trichlorobenzene, few chlorinated benzenes remained in solution and less than the expected amount of benzene was detected. The was explained by nonvolatile products undetected by GC-MS. It is suggested that when higher overpotential mediators are used, the reaction shifts to produce higher molecular weight products by radical-radical coupling reactions. Biphenyl might be a convenient mediator for the dechlorination of polychlorobenzene or even polychlorobiphenyl.

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“…[1][2][3] Figure 1 shows the reduction of hexachlorobenzene in acetonitrile at a glassy carbon electrode. Each peak indicates the loss of one chlorine.…”

Section: Resultsmentioning

confidence: 99%

Section: Mediated Electrolysis Of 124-trichlorobenzene-electrolysismentioning

confidence: 99%

Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

Guena

Wang

Gattrell

et al. 2000

J. Electrochem. Soc.

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“…It should also be recognized that the thermodynamics of dechlorination of polychlorinated cyclohexanes are quite different from those for the dechlorination of polychlorinated benzenes. As is readily shown by voltammetry of a series of chlorinated derivatives, the reduction of polychlorinated benzenes, the removal of a chlorine atom always leads to a product that is more difficult to reduce [1,3,8,9]. In contrast, with lindane it must be concluded that the cleavage of carbon-chlorine bonds leads to species that are more readily reduced and the only stable product is the fully reduced aromatic, benzene.…”

mentioning

confidence: 99%

The Mediated Reduction of Lindane in DMF

et al. 2004

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The direct and mediated reductions of the hexachlorocyclohexane, lindane, in DMF are reported. 9,10-diphenylanthracene (DPA) is a particularly effective mediator. The reaction of DPA À with lindane is a very fast reaction and, indeed, with ratios of [lindane]/[DPA] < 5, the mediated reduction of lindane is mass transfer limited with respect to lindane. During the mediated reduction, light emission can be seen even in an undarkened laboratory; this is due to the formation of DPA*.

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“…The major remediation method for more the accumulation of chlorobenzenes with a higher chlorination level in soils is incineration at high temperatures for digging out of soils. In the previous reports of electrochemical dehalogenation of chlorinated benzenes (Miyoshi et al, 2004;Mohammad and Dennis, 1997;Farwell et al, 1975;Kargina et al, 1997;Guena et al, 2000), the chlorine is eliminated step by step from the highly chlorinated benzenes to yield less-chlorinated benzenes and finally transform to benzene. Farwell et al (1975) reported on chlorobenzenes and the main cathodic reaction pathway for hexachlorobenzenes as follows: hexachlorobenzene → pentachlorobenzene → 1,2,3,5-tetrachlorobenzene → 1,2,4-trichlorobenzene → 1,4-dichlorobenzene → monochlorobenzene → benzene.…”

Section: Degradation Ability For Chlorinated Benzenesmentioning

confidence: 99%

Chemical Degradation of Chlorinated Organic Pollutants for In Situ Remediation and Evaluation of Natural Attenuation

Hara¹

2012

Organic Pollutants Ten Years After the Stockholm Convention - Environmental and Analytical Update

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Reduction pathways of organohalogen compounds

Cited by 70 publications

References 16 publications

Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

The Mediated Reduction of Lindane in DMF

Chemical Degradation of Chlorinated Organic Pollutants for In Situ Remediation and Evaluation of Natural Attenuation

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