Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection,Environmental Science & Technology

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Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection
Environmental Science & Technology ( IF 10.8 ) Pub Date : 2022-11-21 , DOI: 10.1021/acs.est.2c06394
Wanxin Li ₁ , Xiangru Zhang ₁ , Jiarui Han ₁

Affiliation

Acetaminophen is widely used to treat mild to moderate pain and to reduce fever. Under the worldwide COVID-19 pandemic, this over-the-counter pain reliever and fever reducer has been drastically consumed, which makes it even more abundant than ever in municipal wastewater and drinking water sources. Chlorine is the most widely used oxidant in drinking water disinfection, and chlorination generally causes the degradation of organic compounds, including acetaminophen. In this study, a new reaction pathway in the chlorination of acetaminophen, i.e., oxidative coupling reactions via acetaminophen radicals, was investigated both experimentally and computationally. Using an ultraperformance liquid chromatograph coupled to an electrospray ionization-triple quadrupole mass spectrometer, we detected over 20 polymeric products in chlorinated acetaminophen samples, some of which have structures similar to the legacy pollutants “polychlorinated biphenyls”. Both C–C and C–O bonding products were found, and the corresponding bonding processes and kinetics were revealed by quantum chemical calculations. Based on the product confirmation and intrinsic reaction coordinate computations, a pathway for the formation of the polymeric products in the chlorination of acetaminophen was proposed. This study suggests that chlorination may cause not only degradation but also upgradation of a phenolic compound or contaminant.

中文翻译：

氯气消毒中对乙酰氨基酚形成较大分子量消毒副产物

对乙酰氨基酚广泛用于治疗轻度至中度疼痛和退烧。在全球 COVID-19 大流行期间，这种非处方止痛药和退烧药已被大量消耗，这使得它在市政废水和饮用水源中比以往任何时候都更加丰富。氯是饮用水消毒中使用最广泛的氧化剂，氯化通常会导致包括对乙酰氨基酚在内的有机化合物的降解。在这项研究中，对乙酰氨基酚氯化反应的新反应途径，即通过对乙酰氨基酚自由基的氧化偶联反应，在实验和计算上进行了研究。使用耦合到电喷雾电离-三重四极杆质谱仪的超高效液相色谱仪，我们在氯化对乙酰氨基酚样品中检测到 20 多种聚合物产物，其中一些具有类似于遗留污染物“多氯联苯”的结构。发现了C-C和C-O键合产物，并通过量子化学计算揭示了相应的键合过程和动力学。基于产物确认和本征反应坐标计算，提出了对乙酰氨基酚氯化反应中聚合物产物形成的途径。这项研究表明，氯化可能不仅会导致酚类化合物或污染物的降解，还会导致其升级。并通过量子化学计算揭示了相应的键合过程和动力学。基于产物确认和本征反应坐标计算，提出了对乙酰氨基酚氯化反应中聚合物产物形成的途径。这项研究表明，氯化可能不仅会导致酚类化合物或污染物的降解，还会导致其升级。并通过量子化学计算揭示了相应的键合过程和动力学。基于产物确认和本征反应坐标计算，提出了对乙酰氨基酚氯化反应中聚合物产物形成的途径。这项研究表明，氯化可能不仅会导致酚类化合物或污染物的降解，还会导致其升级。

更新日期：2022-11-21

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