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Degradation of chlorinated butenes and butadienes in granular iron columns

机译：粒状铁塔中氯化丁烯和丁二烯的降解

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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-l,4-dichlorobutene-2 (l,4-DCB-2), 3,4-dichlorobutene-l (3,4-DCB-l), 2,3,4-trichlorobutene-1 (TCB), 2-chlorobutadiene-l,3 (chloroprene) and 2,3-dichlorobutadiene-l,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 m~2/mL) than the 2 chlorinated butadienes (t_1/2' ranged from 102 to 197 min mVmL). 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-l and TCB, undergo reductive β-elimination reactions resulting in 1,3-butadiene and chloroprene intermediates. Dechlorination of l,4-DCB-2 to 1,3-butadiene occurs through a reductive elimination similar to reductive β-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.
机译：生产氯丁橡胶的生产设施有可能释放出至少5种氯化丁烯和丁二烯的混合物，包括反式1,4-二氯丁烯-2（l，4-DCB-2），3,4-二氯丁烯-1（ 3,4-DCB-1），2,3,4-三氯丁烯-1（TCB），2-氯丁二烯-1,3（氯丁二烯）和2,3-二氯丁二烯-1,3（DCBD）进入地下水环境。为了评估使用粒状铁修复上述污染物的潜力，进行了一系列柱实验。所有5种化合物的降解均遵循拟一级动力学。三种氯化丁烯的降解速度更快（表面积标准化半衰期，t_1 / 2'，范围为1.6至5.2 min m〜2 / mL）比两种氯化丁二烯（t_1 / 2'，范围为102至197 min mVmL）更快。 。所有颗粒铁都将所有污染物完全脱氯为1,3-丁二烯，作为一种常见的反应中间体，然后降解为相对无害的最终产物的混合物，这些最终产物包括1-丁烯，顺式-2-丁烯，反式-2-丁烯和正丁烷-丁烷。根据动力学数据，产物分布和氯气质量平衡，提出了这些化合物的反应途径。对于氯化丁烯，3,4-DCB-1和TCB进行还原性β消除反应，生成1,3-丁二烯和氯丁二烯中间体。通过类似于还原β-消除的还原消除，将1,4-DCB-2脱氯为1,3-丁二烯。对于两种氯化丁二烯，氯丁二烯和DCBD的脱氯，脱氯是通过氢解途径进行的。常见的非氯化中间体1,3-丁二烯进行催化加氢，生成丁烷异构体和正丁烷的混合物。结果表明，粒状铁是处理被这些化合物污染的地下水的有效材料。

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