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Enhanced formation of trihalomethane disinfection byproducts from halobenzoquinones under combined UV/chlorine conditions

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Abstract

Halobenzoquinones (HBQs) are highly toxic disinfection byproducts (DBPs) and are also precursors of other DBPs such as trihalomethanes (THMs). The formation of THMs from HBQs during chlorine-only and UV/chlorine processes with or without bromide was investigated experimentally. Density functional theory (DFT) reactivity descriptors were also applied to predict the nucleophilic/electrophilic reactive sites on HBQs and intermediates. The results were combined to explain the different behaviors of 2,6-dichloro-1,4-benzoquinone (2,6-DCBQ) and tetrachloro-1,4-benzoquinone (TCBQ) and to propose mechanism for the promoting roles of UV and hydroxylation of HBQs in THMs formation. Under UV/chlorine, UV significantly enhanced THMs formation from 2,6-DCBQ compared to chlorine-only, mainly due to the production of OH-DCBQ*. Excited 2,6-DCBQ* by UV benefited nucleophilic hydrolysis to produce OH-DCBQ*, which favored electrophilic attack by chlorine, thereby inducing more THMs formation. UV/chlorine modestly promoted THMs formation from TCBQ compared to chlorine-only. Hydroxylation of TCBQ and UV irradiation were both important in promoting THMs formation due to the high electrophilic property of OH-TCBQ and TCBQ*. Meanwhile, hydroxylation of HBQs and CHCl3 formation were enhanced at higher pH. This work suggested that enhanced formation of THMs from HBQs should be considered in the application of combined UV and chlorine processes.

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Acknowledgements

This work was supported partly by National Natural Science Foundation of China (Grant No. 51978643) and Youth Innovation Promotion Association, CAS (No. 2014037). The authors thank W.-N. Lee and Dr. G. Zhu at Georgia Tech for analytical assistance.

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Authors and Affiliations

  1. Bei**g Engineering Research Center of Process Pollution Control, Division of Environment Technology and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Bei**g, 100190, China

    He Zhao, Chen Zhong & Penghui Du

  2. School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, GA, 30332, USA

    He Zhao, Ching-Hua Huang & Peizhe Sun

  3. State Environmental Protection Key Laboratory of Integrated Surface Water-Groundwater Pollution Control, School of Environmental Science and Engineering, Southern University of Science and Technology, Shenzhen, 518055, China

    Penghui Du

  4. School of Environmental Science and Engineering, Tian** University, Tian**, 300072, China

    Peizhe Sun

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  1. He Zhao
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  2. Ching-Hua Huang
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  3. Chen Zhong
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  4. Penghui Du
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Correspondence to Ching-Hua Huang.

Additional information

Highlights

• 2,6-DCBQ and TCBQ generated THMs differently in chlorine and UV/chlorine processes.

• UV significantly enhanced hydroxylation of 2,6-DCBQ and CHCl3 formation.

• THMs formation of DCBQ was enhanced due to UV benefitting excited DCBQ* hydrolysis.

• Hydroxylation and UV were both important for TCBQ in promoting THMs formation.

• High pH promoted hydroxylation of HBQs and CHCl3 formation, especially for TCBQ.

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Enhanced formation of trihalomethane disinfection byproducts from halobenzoquinones under combined UV/chlorine conditions

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Zhao, H., Huang, CH., Zhong, C. et al. Enhanced formation of trihalomethane disinfection byproducts from halobenzoquinones under combined UV/chlorine conditions. Front. Environ. Sci. Eng. 16, 76 (2022). https://doi.org/10.1007/s11783-021-1510-7

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  • DOI: https://doi.org/10.1007/s11783-021-1510-7

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