Toxicity of chloroprene, 1,3-dichlorobutene-2, and 1,4-dichlorobutene-2.

Clary, John J.

doi:10.1289/ehp.7721269

Cited by 11 publications

(2 citation statements)

References 6 publications

(7 reference statements)

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“…Solubilities of these compounds range from 256 to 7190 mg/L [1,[4][5][6], suggesting dissolution behaviour is similar to common problematic DNAPL compounds such as trichloroethene (TCE) and tetrachloroethene (PCE). There are no maximum contamination limits (MCLs) for the five chlorinated aliphatics above, however each of the compounds is considered to be toxic [1,[4][5][6][7][8]. Furthermore, 1,4-DCB-2, 3,4-DCB-1 and chloroprene were found to be mutagenic by plate incorporation assay [9] and 1,4-DCB-2, 2,3,4-TCB-1 and chloroprene are considered carcinogenic [1,10,11] while 3,4-DCB-1 is considered a potential carcinogen [5].…”

Section: Introductionmentioning

confidence: 99%

Degradation of chlorinated butenes and butadienes by granular iron

Hughes¹,

Gillham²,

Gui³

2008

WIT Transactions on Ecology and the Environment

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Sites where chlorobutyl rubber is produced have the potential to release a mixture of chlorinated butenes and butadienes, which are known to be toxic and persistent, into the groundwater environment. The potential contaminants include trans-1,4-dichlorobutene-2 (1,4-DCB-2), 3,4-dichlorobutene-1 (3,4-DCB-1), 2,3,4-trichlorobutene-1 (2,3,4-TCB-1), 2-chlorobutadiene-1,3 (chloroprene) and 2,3-dichlorobutadiene-1,3 (DCBD). Granular iron has been shown to reductively dechlorinate a number of compounds and has been used in permeable reactive barriers (PRBs) for in-situ groundwater remediation. To evaluate the possibility of using granular iron for the remediation of the above contaminants, a series of batch experiments were conducted. Results show that dechlorination reactions for chlorinated butenes closely followed pseudo-first-order kinetics with normalized half-lives ranging from 5.1 to 7.5 h. Chlorinated butadienes degraded much slower in batch tests with normalized half-lives ranging from 38.8 to 128 h. Chlorine mass balance calculations showed that 1,4-DCB-2, 3,4-DCB-1 and chloroprene were fully dechlorinated by granular iron. 2,3,4-TCB-1 was transformed to chloroprene as an intermediate via a reductive β-elimination pathway. Neither the presence of CaCO 3 nor temperature affected degradation rates suggesting that mass transport to iron surfaces was limiting degradation in batch tests. A column experiment was conducted on 3,4-DCB-1 and a normalized half-life of 1.6 min was found. Faster degradation in the column was thought to be due to enhanced mixing effects. 3,4-DCB-1 was converted to 1,3-butadiene via reductive β-elimination, which was then converted to a mixture of 1-butene, cis-2-butene and trans-2-butene via catalytic hydrogenation.

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Section: Introductionmentioning

confidence: 99%

Degradation of chlorinated butenes and butadienes by granular iron

Hughes¹,

Gillham²,

Gui³

2008

WIT Transactions on Ecology and the Environment

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“…[1,[3][4][5][6][7] 1,4-DCB-2, 3,4-DCB-1 and chloroprene were found to be mutagenic by plate incorporation assay; [8] 1,4-DCB-2, TCB and chloroprene are considered carcinogenic [1,9,10] and 3,4-DCB-1 is considered a potential carcinogen. [4] Thus their release into the environment could have detrimental effects on human and environmental health.…”

Section: Introductionmentioning

confidence: 99%

Degradation of chlorinated butenes and butadienes in granular iron columns

Hughes

Gui

Gillham

2009

Journal of Environmental Science and Health, Part A

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Manufacturing facilities for production of chlorobutyl rubber have the potential to release a mixture of at least 5 chlorinated butenes and butadienes including trans-1,4-dichlorobutene-2 (1,4-DCB-2), 3,4-dichlorobutene-1 (3,4-DCB-1), 2,3,4-trichlorobutene-1 (TCB), 2-chlorobutadiene-1,3 (chloroprene) and 2,3-dichlorobutadiene-1,3 (DCBD) into groundwater environment. To evaluate the potential of using granular iron in the remediation of the above contaminants, a series of column experiments were conducted. Degradation of all 5 compounds followed pseudo-first-order kinetics. The three chlorinated butenes degraded much faster (surface area normalized half-lives, t(1/2)', ranged from 1.6 to 5.2 min m2/mL) than the 2 chlorinated butadienes (t(1/2)' ranged from 102 to 197 min m2/mL). All contaminants fully dechlorinated by granular iron to 1,3-butadiene as a common reaction intermediate that then degraded to a mixture of relatively non-harmful end products consisting of 1-butene, cis-2-butene, trans-2-butene and n-butane. Based on the kinetic data, product distributions, and chlorine mass balances, reaction pathways for these compounds are proposed. For the chlorinated butenes, 3,4-DCB-1 and TCB, undergo reductive beta-elimination reactions resulting in 1,3-butadiene and chloroprene intermediates. Dechlorination of 1,4-DCB-2 to 1,3-butadiene occurs through a reductive elimination similar to reductive beta-elimination. For dechlorination of the two chlorinated butadienes, chloroprene and DCBD, dechlorination occurs through a hydrogenolysis pathway. The common non-chlorinated intermediate, 1,3-butadiene, undergoes catalytic hydrogenation resulting in a mixture of butane isomers and n-butane. The results suggest that granular iron is an effective material for treatment of groundwater contaminated with these compounds.

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1,3-Dichloro-2-butene

Conrow

2001

Encyclopedia of Reagents for Organic Synthesis

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Toxicity of chloroprene, 1,3-dichlorobutene-2, and 1,4-dichlorobutene-2.

Cited by 11 publications

References 6 publications

Degradation of chlorinated butenes and butadienes by granular iron

Degradation of chlorinated butenes and butadienes by granular iron

Degradation of chlorinated butenes and butadienes in granular iron columns

1,3-Dichloro-2-butene

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