Halogenated benzoquinones (HBQs) are frequently detected in tap water. HBQ levels are correlated with water age. As the water-transmission distance (water age) increases, the levels of bromo-benzoquinones (Br-BQs) decreased and those of chloro-benzoquinones (Cl-BQs) remained relatively stable in drinking water-distribution system in the presence of residual chlorine. 2,3,5,6-Tetrachloro-1,4-benzoquinone (TCBQ) and 2,6-dibromo-1,4-benzoquinone (DBBQ) were the most abundant Cl-BQ and Br-BQ, with maximum concentrations of 60.2 and 181.4 ng/L, respectively. TCBQ and DBBQ were chosen as representatives of HBQs to investigate their reactions with chlorine, including kinetics, pathways, and changes in toxicity. The hydrolysis and chlorination rates of HBQs were significantly pH-dependent, and the kinetic rates of DBBQ were faster than TCBQ in the pH range of 5-10. Chlorination converted highly toxic TCBQ and DBBQ to less-toxic chlorinated/brominated aliphatic disinfection by-products (DBPs), thereby reducing the overall toxicity of water bodies. This study provides comprehensive insights into the distinct life cycles of TCBQ and DBBQ in drinking water, covering formation, transformation, and toxicity. These findings provide a nuanced understanding of the risks posed by HBQs at various locations within the drinking water distribution system, offering valuable guidance for improving the control of DBPs in drinking water.
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Chloro- and bromo-benzoquinone formation and transformation mechanisms in a drinking water-distribution system.
J Hazard Mater
January 2024
College of Environmental Science and Engineering, Donghua University, 2999 North Renmin Road, Shanghai 201620, China; Shanghai institute of pollution control and ecological security, Shanghai 200092, China. Electronic address:
Halogenated benzoquinones (HBQs) are frequently detected in tap water. HBQ levels are correlated with water age. As the water-transmission distance (water age) increases, the levels of bromo-benzoquinones (Br-BQs) decreased and those of chloro-benzoquinones (Cl-BQs) remained relatively stable in drinking water-distribution system in the presence of residual chlorine.
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Environ Mol Mutagen
June 2020
Key Laboratory of Drinking Water Science and Technology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing, China.
Recently, halobenzoquinones (HBQs) disinfection byproducts, including 2,6-dichloro-1, 4-benzoquinone (DCBQ), 2,6-dichloro-3-methyl-1, 4-benzoquinone (DCMBQ), 2,3,6-trichloro-1, 4-benzoquinone (TCBQ), and 2,6-dibromobenzoquinone (DBBQ), have been of increasing concern due to their reported ability to induce oxidative damage, and thus genotoxicity. However, data on the risk of genotoxicity due to chromosomal damage by HBQs are still scarce. Here, the cytotoxicity and genotoxicity of the four HBQs were assessed using human cell lines (bladder cancer 5637 cells, colon carcinoma Caco-2 cells, and gastric MGC-803 cells).
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Anal Chim Acta
October 2018
School of Environment and Civil Engineering, Dongguan University of Technology, Dongguan, China; Guangdong Engineering and Technology Research Center for Advanced Nanomaterials, Dongguan University of Technology, Dongguan, China. Electronic address:
Halobenzoquinones (HBQs) were reported as disinfection byproducts (DBPs) which had potential risk of bladder cancer. In this paper, a highly selective analytical method for HBQs was developed by HBQs-mediated assembly of amino acid modified Mn-doped ZnS/Quantum Dots (Mn: ZnS QDs). In the presence HBQs, a charge-transfer complex (CTC) was formed between aromatic rings of HBQs and the primary amino groups on the surface of the QDs.
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Environ Sci Technol
August 2015
†Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta, Canada T6G 2G3.
Halobenzoquinones (HBQs) widely occur in drinking water treatment plant (DWTP) effluents; however, HBQ precursors and their removal by treatments remain unclear. Thus, we have investigated HBQ precursors in plant influents and their removal by each treatment before chlorination in nine DWTPs. The levels of HBQ precursors were determined using formation potential (FP) tests for 2,6-dichloro-1,4-benzoquinone (DCBQ), 2,3,6-trichloro-1,4-benzoquinone (TCBQ), 2,6-dichloro-3-methyl-1,4-benzoquinone (DCMBQ), and 2,6-dibromo-1,4-benzoquinone (DBBQ).
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Environ Sci Technol
May 2013
Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, Alberta, Canada, T6G 2G3.
Halobenzoquinones (HBQs) are a group of emerging disinfection byproducts (DBPs) found in treated drinking water. Because the use of UV treatment for disinfection is becoming more widespread, it is important to understand how the HBQs may be removed or changed due to UV irradiation. Water samples containing four HBQs, 2,6-dichloro-1,4-benzoquinone (DCBQ), 2,3,6-trichloro-1,4-benzoquinone (TCBQ), 2,6-dichloro-3-methyl-1,4-benzoquinone (DCMBQ), and 2,6-dichloro-1,4-benzoquinone (DBBQ), were treated using a modified bench scale collimated beam device, mimicking UV treatment.
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