Recently, the combination of peroxymonosulfate (PMS) and hydroxylamine (HA) has been proposed as a green and efficient sulfate radical (

)-based advanced oxidation process (AOP) for eliminating organic contaminants. However, we found that toxic nitrosated and nitrated aromatic compounds were generated during the treatment of phenolic compounds by PMS/HA system, indicating the involvement of reactive nitrogen species (RNS) during the interaction of PMS with HA. Specifically, considerable production of p-nitrosophenol (p-NSP) and mononitrophenol were obtained when phenol was oxidized by PMS/HA system under various conditions. At the molar ratio between HA and PMS of 1.0 and pH 5.0, sum of the yields of p-NSP and nitrophenols reached their maxima (around 50%). Moreover, production of p-NSP was inhibited while that of nitrophenols was promoted when applied NH₂OH1/2H₂SO₄ was replaced by NH₂OHHCl, which was possibly related to the formation of secondary reactive species induced by the reaction of

with chloride ion. Further, formation of undesirable nitrosated and nitrated aromatic products was obtained in the treatment of other phenolic compounds including acetaminophen, bisphenol A, and bisphenol S by PMS/HA system. Considering the toxicity of nitrosated and nitrated aromatic compounds, practical application of PMS/HA system for environmental decontamination should be scrutinized.

中文翻译：

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过氧单硫酸盐和羟胺的组合处理苯酚中的亚硝化和硝化芳烃产物的形成

最近，过氧单硫酸盐 (PMS) 和羟胺 (HA) 的组合被提出作为一种绿色有效的硫酸根自由基。

) 的高级氧化工艺 (AOP)，用于消除有机污染物。然而，我们发现在通过 PMS/HA 系统处理酚类化合物的过程中会产生有毒的亚硝化和硝化芳族化合物，这表明在 PMS 与 HA 相互作用期间活性氮物质 (RNS) 的参与。具体而言，当苯酚在各种条件下被 PMS/HA 系统氧化时，获得了大量的对亚硝基苯酚( p- NSP) 和单硝基苯酚。在 HA 和 PMS 之间的摩尔比为 1.0 和 pH 值为 5.0 时，p- NSP 和硝基苯酚的产量总和达到最大值（约 50%）。此外，当应用NH时，p- NSP的产生受到抑制，而硝基苯酚的产生得到促进。₂ OH 1/2H ₂ SO ₄被NH ₂ OH HCl取代，这可能与

与氯离子。此外，在通过 PMS/HA 系统处理包括对乙酰氨基酚、双酚 A 和双酚 S 在内的其他酚类化合物时，会形成不良的亚硝化和硝化芳烃产物。考虑到亚硝化和硝化芳香族化合物的毒性，应仔细审查 PMS/HA 系统在环境净化中的实际应用。