Voltammetric investigation of the dissociative electron transfer to polychloromethanes at catalytic and non-catalytic electrodes

Isse, Abdirisak Ahmed; Sandonà, Giancarlo; Durante, Christian; Gennaro, Armando

doi:10.1016/j.electacta.2008.12.034

Cited by 69 publications

(84 citation statements)

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“…We attribute this potential shift to the well-known catalytic effects of silver as a cathode material for carbon-chlorine bond cleavage, as reported in literature. [18][19][20][21][22][23][24][25] It is interesting that there is little shift in the peak potential for the second stage of reduction when glassy carbon is compared with silver; furthermore, the third and fourth cathodic peak potentials are independent of cathode material.…”

Section: Resultsmentioning

confidence: 99%

“…[18][19][20] Recently, it has been shown in our laboratory that the position and identity of the halogen atom affect the reduction potential and mechanism. 21,22 Research from the groups of Isse 23,24 and Amatore 25 has provided further insight concerning the mechanisms of electroreductive carbon-chlorine bond cleavage at silver cathodes; it has been determined that activated species adsorb onto the silver surface, thereby promoting the observed catalytic effects. In the present work, cyclic voltammetry and controlled-potential (bulk) electrolysis have been used to investigate the electrochemical reduction of methoxychlor at carbon and silver cathodes in DMF containing 0.050 M tetra-n-butylammonium tetrafluoroborate (TBABF 4 ) as supporting electrolyte.…”

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confidence: 99%

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Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

McGuire

Peters

2016

J. Electrochem. Soc.

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Cyclic voltammetry and controlled-potential (bulk) electrolysis have been employed to investigate the electrochemical reduction of 4,4 -(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene), commonly known as the pesticide methoxychlor, at glassy carbon and silver cathodes in dimethylformamide (DMF) containing 0.050 M tetra-n-butylammonium tetrafluoroborate (TBABF 4 ). Reduction of methoxychlor at both glassy carbon and silver shows four voltammetric peaks, the first three of which are associated with cleavage of carbon-chlorine bonds; the fourth peak is assigned to reduction of 4,4 -(ethene-1,1-diyl)bis(methoxybenzene). Bulk electrolyses of methoxychlor at reticulated vitreous carbon and silver mesh cathodes at potentials corresponding to each of the first three voltammetric peaks were conducted; coulometric n values and product distributions (determined by means of GC and GC-MS techniques) depend on potential. In particular, two completely dechlorinated products, namely 4,4 -(ethane-1,1-diyl)bis(methoxybenzene) and 4,4 -(ethene-1,1-diyl)bis(methoxybenzene) have been identified and quantitated. A mechanistic scheme is proposed to account for the formation of the various products. When global use of the infamous pesticide 4,4 -(2,2,2-trichloroethane-1,1-diyl)bis(chlorobenzene) (1)-known more familiarly as DDT-was restricted, a close relative, namely 4,4 -(2,2,2-trichloroethane-1,1-diyl)bis(methoxybenzene) (2) or methoxychlor, became a temporarily popular replacement. Unfortunately, when concerns about the toxicity of 2 arose, it was banned in the European Union in 2002 and became unregistered in the United States in 2003. However, in other parts of the world, 2 is still employed as an agricultural pesticide and for home applications in the treatment of flea and fly infestations.Like many members of the family of halogenated pesticides, methoxychlor degrades very slowly in the environment, which allows for its transport and subsequent detection in Arctic samples far from the original point of use.1 For hydrolytic degradation pathways in aquatic systems of pH 6-9, the half-life is approximately one year, and the resulting olefinic metabolite degrades even more slowly.2 When exposed to sunlight, this olefin derivative undergoes an interesting photoisomerization in water.3 Sunlight increases the photolysis rate, so that the half-life at the surface of distilled water is closer to 4.5 months, and even faster in natural waters where half-lives of only 2-5 h are seen. 4 Biological degradation of methoxychlor results in the loss of one chlorine as well as demethylation of the hydroxylbenzene moieties.5 Uptake of methoxychlor in a model ecosystem has also been examined; whereas methoxychlor was found to be in a dynamic state in fish, it accumulated in snails. Furthermore, incubated mouse livers were unable to metabolize methoxychlor and 97% was recovered. 6 Concerns about the accumulation of methoxychlor in humans prompted studies conducted in the agricultural region of Spain * Electrochemical Society Student Member. * * E...

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

McGuire

Peters

2016

J. Electrochem. Soc.

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“…Although many studies have investigated electroreduction and electrocarboxylation of organic chlorides, most of them focused on monochloride compounds [19,21,22,[40][41][42][43][44]. Only a few studies have examined the electroreduction of polyhalidecompounds [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59], such as dichloromethane, trichloromethane, tetrachloromethane, and hexachlorocyclohexane.…”

Section: Introductionmentioning

confidence: 99%

Electrocarboxylation of Dichlorobenzenes on a Silver Electrode in DMF

et al. 2017

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Carbon dioxide (CO 2 ) is the largest contributor to the greenhouse effect, and fixing and using this greenhouse gas in a facile manner is crucial. This work investigates the electrocarboxylation of dichlorobenzenes with the atmospheric pressure of CO 2 in an undivided cell with an Ag cathode and an Mg sacrificial anode. The corresponding carboxylic acids and their derivatives, which are important industrial and fine chemicals, are obtained. To deeply understand this reaction, we investigate the influence of various reaction conditions, such as supporting electrolyte, current density, electric charge, and reaction temperature, on the electrocarboxylation yield by using 1,4-dichlorobenzene as the model compound. The electrochemical behavior of dichlorobenzenes is studied through cyclic voltammetry. The relation among the distinct electronic effects of dichlorobenzenes, the electrochemical characteristics of their reduction, and the distribution law of target products is also established.

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“…For this reason, the electrochemical reductive cleavage of carbon-halogen bonds in organic compounds, with the particular focus on volatile organic halides, has been mainly studied and developed in the last decades [10][11][12][13] being the subject of numerous studies in aqueous [14][15][16], non aqueous [17][18][19] and mixed solvents [13,20]. The great interest for this process is due to its important role in some environmental applications, such as the abatement of volatile polychlorinated organic compounds, a group of pollutants having hazardous effects on living beings and out of the scope of most EAOPs.…”

Section: Introductionmentioning

confidence: 99%

Rapid screening of silver nanoparticles for the catalytic degradation of chlorinated pollutants in water

Lugaresi

Perales-Rondón

Minguzzi

et al. 2015

Applied Catalysis B: Environmental

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Please cite this article as: O. Lugaresi, J.V. Perales-Rondón, A. Minguzzi, J. SollaGullón, S. Rondinini, J.M. Feliu, C.M. Sánchez-Sánchez, Rapid screening of silver nanoparticles for the catalytic degradation of chlorinated pollutants in water, Applied Catalysis B, Environmental (2014), http://dx.doi.org/10. 1016/j.apcatb.2014.08.030 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. We suggest the proper size range and the presence of abundant superficial defective sites, such as steps or kinks, as the main reasons for Ag NPs C1 exhibiting the best overall catalytic performance in trichloromethane electrochemical reduction.

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Voltammetric investigation of the dissociative electron transfer to polychloromethanes at catalytic and non-catalytic electrodes

Cited by 69 publications

References 38 publications

Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

Electrocarboxylation of Dichlorobenzenes on a Silver Electrode in DMF

Rapid screening of silver nanoparticles for the catalytic degradation of chlorinated pollutants in water

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Voltammetric investigation of the dissociative electron transfer to polychloromethanes at catalytic and non-catalytic electrodes

Cited by 69 publications

References 38 publications

Direct Electrochemical Reduction of 4,4′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

Direct Electrochemical Reduction of 4,4′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

Electrocarboxylation of Dichlorobenzenes on a Silver Electrode in DMF

Rapid screening of silver nanoparticles for the catalytic degradation of chlorinated pollutants in water

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Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide

Direct Electrochemical Reduction of 4,4^′-(2,2,2-Trichloroethane-1,1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide