Direct Electrochemical Reduction of 4, 4′-(2, 2, 2-Trichloroethane-1, 1-diyl)bis(methoxybenzene) (Methoxychlor) at Carbon and Silver Cathodes in Dimethylformamide. Issue 5 (5th February 2016)

• Record Type: Journal Article
• Authors: McGuire, Caitlyn M.; Peters, Dennis G.
• Is Part Of: Journal of the Electrochemical Society. Volume 163:Issue 5(2016)
• Page Start: G44
• Page End: G49
• Publication Date: 2016-02-05
• Subjects: Carbon-chlorine bond cleavage -- Electrochemical reduction -- Glassy carbon cathode -- Methoxychlor -- Silver cathode; Electrochemistry -- Periodicals; 541.3705
• DOI: 10.1149/2.0921605jes
• Languages: English
• ISSNs: 0013-4651

Abstract

Abstract : 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 (TBABF4 ). 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.