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1,1,2,2-Tetrachloroethane Reactions with OH-, Cr(II), Granular Iron, and a Copper−Iron Bimetal: Insights from Product Formation and Associated Carbon Isotope Fractionation

Environmental science & technology, 2007-06, Vol.41 (11), p.4111-4117 [Peer Reviewed Journal]

Copyright © 2007 American Chemical Society ;2007 INIST-CNRS ;Copyright American Chemical Society Jun 1, 2007 ;ISSN: 0013-936X ;EISSN: 1520-5851 ;DOI: 10.1021/es063040x ;PMID: 17612198 ;CODEN: ESTHAG

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Title:
1,1,2,2-Tetrachloroethane Reactions with OH-, Cr(II), Granular Iron, and a Copper−Iron Bimetal: Insights from Product Formation and Associated Carbon Isotope Fractionation
Author: Elsner, Martin ; Cwiertny, David M ; Roberts, A. Lynn ; Sherwood Lollar, Barbara
Subjects: Applied sciences ; Carbon ; Carbon Isotopes ; Chemical bonds ; Chemical Fractionation ; Chemistry ; Chromium - chemistry ; Copper ; Copper - chemistry ; Earth sciences ; Earth, ocean, space ; Engineering and environment geology. Geothermics ; Ethane - analogs & derivatives ; Ethane - chemistry ; Exact sciences and technology ; Fractionation ; Groundwaters ; Hydrocarbons, Chlorinated - chemistry ; Hydroxides - chemistry ; Iron ; Iron - chemistry ; Isotopes ; Kinetics and mechanisms ; Natural water pollution ; Organic chemistry ; Pollution ; Pollution, environment geology ; Reactivity and mechanisms ; Water Pollutants, Chemical - chemistry ; Water treatment and pollution
Is Part Of: Environmental science & technology, 2007-06, Vol.41 (11), p.4111-4117
Description: Despite widespread implementation of zero-valent iron remediation schemes, the manner and order of chemical bond cleavage in iron-mediated organohalide transformations remains imperfectly understood. We present insights from carbon isotope fractionation for the dehalogenation of 1,1,2,2-tetrachloroethane (1,1,2,2-TeCA) and 1,1,1-trichloroethane (1,1,1-TCA) by various reactants. Elimination of HCl by OH- gave isotope fractionation in 1,1,2,2-TeCA of ε = −25.6‰, KIEC = 1.02 to 1.03 per carbon center, consistent with a concerted (E2) mechanism. In contrast, 1,1,1-TCA reduction by Cr(II), Fe(0), and Cu-plated iron (Cu/Fe) resulted in ε = −13.6‰ to −15.8‰ indicating the initial involvement of a single C−Cl bond (KIEC ≈ 1.03). 1,1,2,2-TeCA reduction by Cr(II), Fe(0), and Cu/Fe yielded ε = −18.7‰, −19.3‰, and −17.0‰, respectively. In the two latter cases, depletion of the minor product TCE by 26‰ indicated its formation via nonreductive dehydrohalogenation. The major 1,1,2,2-TeCA reduction products, cis- and trans-DCE, differed by 2.3‰ ± 1.0‰ in Cr(II) systems, but were equivalent in Fe(0) and Cu/Fe systems. In contrast, the ratio of cis-DCE to trans-DCE concentration was 2.5 for reduction with Cr(II) and Fe(0), but ∼3.8 with Cu/Fe. Complementary isotope and concentration data therefore suggest differences in the transition state geometry and/or reaction intermediates in each reductant system.
Publisher: Washington, DC: American Chemical Society
Language: English
Identifier: ISSN: 0013-936X
EISSN: 1520-5851
DOI: 10.1021/es063040x
PMID: 17612198
CODEN: ESTHAG
Source: MEDLINE
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1,1,2,2-Tetrachloroethane Reactions with OH-, Cr(II), Granular Iron, and a Copper−Iron Bimetal: Insights from Product Formation and Associated Carbon Isotope Fractionation

Copyright © 2007 American Chemical Society ;2007 INIST-CNRS ;Copyright American Chemical Society Jun 1, 2007 ;ISSN: 0013-936X ;EISSN: 1520-5851 ;DOI: 10.1021/es063040x ;PMID: 17612198 ;CODEN: ESTHAG

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