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Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection.
Li, Wanxin; Zhang, Xiangru; Han, Jiarui.
  • Li W; Department of Civil and Environmental Engineering, The Hong Kong University of Science and Technology, Hong Kong SAR00000, China.
  • Zhang X; Department of Civil and Environmental Engineering, The Hong Kong University of Science and Technology, Hong Kong SAR00000, China.
  • Han J; Department of Civil and Environmental Engineering, The Hong Kong University of Science and Technology, Hong Kong SAR00000, China.
Environ Sci Technol ; 56(23): 16929-16939, 2022 Dec 06.
Article in English | MEDLINE | ID: covidwho-2133140
ABSTRACT
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.
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Full text: Available Collection: International databases Database: MEDLINE Main subject: Water Pollutants, Chemical / Drinking Water / Water Purification / Disinfectants / COVID-19 Limits: Humans Language: English Journal: Environ Sci Technol Year: 2022 Document Type: Article Affiliation country: Acs.est.2c06394

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Full text: Available Collection: International databases Database: MEDLINE Main subject: Water Pollutants, Chemical / Drinking Water / Water Purification / Disinfectants / COVID-19 Limits: Humans Language: English Journal: Environ Sci Technol Year: 2022 Document Type: Article Affiliation country: Acs.est.2c06394