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首页> 美国卫生研究院文献>other >Mechanism of Intrinsic Chemiluminescence Production from the Degradation of Persistent Chlorinated Phenols by Fenton System: A Structure-Activity Relationship Study and the Critical Role of Quinoid and Semiquinone Radical Intermediates
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Mechanism of Intrinsic Chemiluminescence Production from the Degradation of Persistent Chlorinated Phenols by Fenton System: A Structure-Activity Relationship Study and the Critical Role of Quinoid and Semiquinone Radical Intermediates

机译：Fenton体系降解持久性氯化苯酚的内在化学发光机理：结构-活性关系研究及醌型和半醌型自由基中间体的关键作用

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摘要

We found recently that intrinsic chemiluminescence (CL) could be produced by all 19 chlorophenolic persistent organic pollutants during environmentally-friendly advanced oxidation processes. However, the underlying mechanism for the structure-activity relationship (SAR, i.e., the chemical structures and the CL generation) remains unclear. In this study, we found that, for all 19 chlorophenol congeners tested, the CL increased with increasing number of chlorine atoms in general; and for chlorophenol isomers (such as the 6 trichlorophenols), the CL decreased in the order of meta- > ortho-/para-Cl-substituents with respect to the -OH group of chlorophenols. Further studies showed that not only chlorinated quinoid intermediates, but more interestingly, chlorinated semiquinone radicals were produced during the degradation of trichlorophenols by Fenton reagent; and the type and yield of which were determined by the directing effects, hydrogen bonding and steric hindrance effect of the OH- and/or Cl-substitution groups. More importantly, a good correlation was observed between the formation of these quinoid intermediates and CL generation, which could fully explain the above SAR findings. This represents the first report on the structure-activity relationship study and the critical role of quinoid and semiquinone radical intermediates, which may have broad chemical and environmental implications for future studies on remediation of other halogenated persistent organic pollutants by advanced oxidation processes.
机译：我们最近发现，在环境友好的高级氧化过程中，所有19种氯酚类持久性有机污染物均可能产生内在化学发光（CL）。但是，结构-活性关系（SAR，即化学结构和CL的产生）的基本机理仍不清楚。在这项研究中，我们发现，对于所测试的所有19种氯酚同类物，CL通常随着氯原子数目的增加而增加；对于氯酚异构体（例如6种三氯酚），相对于氯酚的-OH基团，CL依次以间->邻-/对-Cl-取代基的顺序降低。进一步的研究表明，在Fenton试剂降解三氯酚的过程中，不仅氯化醌类中间体，而且更有趣的是产生了氯化半醌基。其类型和收率由OH和/或Cl取代基团的定向作用，氢键作用和位阻作用决定。更重要的是，在这些醌型中间体的形成与CL生成之间观察到良好的相关性，可以充分解释上述SAR结果。这是关于结构-活性关系研究以及醌类和半醌类自由基中间体的关键作用的第一份报告，这可能对今后通过高级氧化工艺修复其他卤代持久性有机污染物的研究具有广泛的化学和环境影响。

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