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首页> 外文期刊>Environmental Science & Technology >Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone imine
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Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone imine

机译:通过氯化转化对乙酰氨基酚产生毒物1,4-苯醌和N-乙酰基-对苯醌亚胺

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The reaction of the common pain reliever acetaminophen (paracetamol, 4-acetamidophenol) with hypochlorite was investigated over time under conditions that simulate wastewater disinfection. Initially, the reaction was studied in pure water at neutral pH (7.0), a range of reaction times (2-90 min), and a molar excess of hypochlorite (2-57 times) relative to the acetaminophen concentration. The reaction was monitored using reversed-phase liquid chromatography (LC) with ultraviolet absorbance, electrochemical, and mass spectrometric detection. At 1 mu mol/L (150 ppb) and 10 mu mol/L (1.5 ppm) levels, acetaminophen readily reacted to form at least 11 discernible products, all of which exhibited greater LC retention than the parent. Two of the products were unequivocally identified as the toxic compounds 1,4-benzoquinone and N-acetyl-p-benzoquinone imine (NAPQI, which is the toxicant associated with lethality in acetaminophen overdoses. With a hypochlorite dose of 57 mu mol/L (4 ppm as Cl-2) 88% of the acetaminophen (10,mu mol/L initial) was transformed in I h. The two quinoidal oxidation products 1,4-benzoquinone and NAPQI accounted for 25% and 1.5% of the initial acetaminophen concentration, respectively, at a I h reaction time. Other products that were identified included two ring chlorination products, chloro-4-acetamidophenol and dichloro-4-acetamidophenol, which combined were approximately 7% of the initial acetaminophen concentration at 1 h. The reaction was also studied in wastewater, where similar reactivity was noted. These results demonstrate that acetaminophen is likely to be transformed significantly during wastewater chlorination. The reactivity of the chlorine-transformation products was also studied with sulfite to simulate dechlorination, and 1,4-benzoquinone and NAPQI were completely reduced.
机译:在模拟废水消毒的条件下,随时间推移研究了常见的止痛药对乙酰氨基酚(对乙酰氨基酚,4-乙酰氨基苯酚)与次氯酸盐的反应。最初,在中性pH(7.0),反应时间范围(2-90分钟)和次氯酸盐相对于对乙酰氨基酚浓度而言摩尔过量(2-57倍)的纯水中研究了反应。使用具有紫外吸收,电化学和质谱检测的反相液相色谱(LC)监测反应。在1μmol / L(150 ppb)和10μmol / L(1.5 ppm)的水平下,对乙酰氨基酚容易反应形成至少11种可分辨的产物,所有这些产物均比母体具有更大的LC保留。明确地确定了其中两种产品为有毒化合物1,4-苯醌和N-乙酰基-对苯醌亚胺(NAPQI),它是对乙酰氨基酚过量致死性的有毒物质。次氯酸盐剂量为57μmol / L( 4 ppm(以Cl-2计)在1 h内转化了88%的对乙酰氨基酚(初始浓度为10μmol/ L),两种醌型氧化产物1,4-苯醌和NAPQI分别占初始对乙酰氨基酚的25%和1.5%在1小时的反应时间中,其浓度分别为2环氯化反应产物,即氯-4-对乙酰氨基苯酚和二氯-4-对乙酰氨基苯酚,两者合计约为1小时对乙酰氨基酚初始浓度的7%。还对废水中的反应进行了研究,发现其反应性相似,这些结果表明对乙酰氨基酚在废水氯化过程中可能会被显着转化,氯转化产物的反应性也得到了研究。 d用亚硫酸盐模拟脱氯,完全还原了1,4-苯醌和NAPQI。

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