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首页> 外文期刊>RSC Advances >Reductive dechlorination of endosulfan isomers and its metabolites by zero-valent metals: reaction mechanism and degradation products
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Reductive dechlorination of endosulfan isomers and its metabolites by zero-valent metals: reaction mechanism and degradation products

机译：零价金属对硫丹异构体及其代谢物的还原脱氯：反应机理和降解产物

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摘要

The widely used organochlorine pesticide endosulfan (ES) is extremely toxic to fishes, other aquatic species and mammals. Current evidence suggests that all known natural attenuation residues of ES, i.e., ES-metabolites, retain the original chlorinated skeleton of ES and are potential carcinogens. The objective of the present study was to identify the dechlorinated products formed during the reduction of ES-isomers, i.e., endosulfan-1 and endosulfan-2 and ES-metabolites, namely endosulfan sulfate (ES-S), endosulfan lactone (ES-L), endosulfan ether (ES-E) and endosulfan alcohol (ES-A), by various metallic surfaces. During dechlorination by nano zero-valent iron (NZVI), the mass spectra of the degradation products were consistent with the loss of one, two and three chlorine atoms from the parent molecules. During the interaction of ES-E with Mg0, the degradation products had mass spectra consistent with the loss of 1–6 chlorine atoms from the parent molecule. In all cases, dechlorination appears to occur through sequential electron transfer at the metallic surface. Tentative chemical structures for various degradation products were proposed. Synthesis of some of the observed degradation products was possible using ES-E as the starting molecule. 1H NMR, crystallographic (X-ray diffraction) and GC-MS analysis of the synthesized products provide final confirmation of the proposed chemical structures. A pathway for stepwise reductive dechlorination of ES-isomers and metabolites is proposed. Some of the degradation products identified in the present study being less chlorinated, may be less toxic and more amenable to subsequent biodegradation and ultimate mineralization in the natural environment.
机译：广泛使用的有机氯农药硫丹（ES）对鱼类，其他水生物和哺乳动物具有极高的毒性。当前证据表明，所有已知的ES自然衰减残基，即ES代谢物，都保留了ES的原始氯化骨架，并且是潜在的致癌物。本研究的目的是鉴定在还原ES异构体（ ie ），硫丹1和硫丹2和硫丹代谢物的过程中形成的脱氯产物，即硫酸硫丹（ES-S） ，硫丹内酯（ES-L），硫丹醚（ES-E）和硫丹醇（ES-A），通过各种金属表面形成。在纳米零价铁（NZVI）脱氯过程中，降解产物的质谱与母体分子中一个，两个和三个氯原子的损失一致。在ES-E与Mg 0 相互作用期间，降解产物的质谱与从母体分子损失的1-6个氯原子一致。在所有情况下，脱氯似乎都是通过在金属表面上依次进行电子转移而发生的。提出了各种降解产物的初步化学结构。使用ES-E作为起始分子，可以合成某些观察到的降解产物。合成产物的 1 H NMR，晶体学（X射线衍射）和GC-MS分析为所提出的化学结构提供了最终确认。提出了ES-异构体和代谢物逐步还原脱氯的途径。在本研究中确定的某些降解产物氯化程度较低，毒性较低，并且更适合自然环境中的后续生物降解和最终矿化作用。

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