Formation of Larger Molecular Weight Disinfection Byproducts from Acetaminophen in Chlorine Disinfection.
Wanxin LiXiangru ZhangJiarui HanPublished in: Environmental science & technology (2022)
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.
Keyphrases
- drinking water
- liver injury
- health risk
- health risk assessment
- drug induced
- chronic pain
- drug delivery
- mass spectrometry
- molecular dynamics
- wastewater treatment
- pain management
- neuropathic pain
- risk assessment
- cancer therapy
- spinal cord
- ms ms
- anti inflammatory
- drug release
- quantum dots
- sewage sludge
- anaerobic digestion