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

doi:10.1007/s11783-021-1510-7

Front. Environ. Sci. Eng.

2022, Vol. 16

Issue (6) : 76 https://doi.org/10.1007/s11783-021-1510-7

RESEARCH ARTICLE

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

He Zhao^1,², Ching-Hua Huang²(

), Chen Zhong¹, Penghui Du^1,³, Peizhe Sun^2,⁴

¹. Beijing Engineering Research Center of Process Pollution Control, Division of Environment Technology and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China
². School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, GA 30332, USA
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
⁴. School of Environmental Science and Engineering, Tianjin University, Tianjin 300072, China

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Abstract

• 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.

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.

Keywords Halobenzoquinone Trihalomethane Chlorine disinfection UV irradiation Disinfection byproducts Combined UV/chlorine

Corresponding Author(s): Ching-Hua Huang

Issue Date: 11 October 2021

Cite this article:

He Zhao,Ching-Hua Huang,Chen Zhong, et al. Enhanced formation of trihalomethane disinfection byproducts from halobenzoquinones under combined UV/chlorine conditions[J]. Front. Environ. Sci. Eng., 2022, 16(6): 76.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-021-1510-7
https://academic.hep.com.cn/fese/EN/Y2022/V16/I6/76

Fig.1 Formation of chloroform from (a) CBQ, (b) 2,5-DCBQ, (c) 2,6-DCBQ and (d) TCBQ as a function of time by chlorine and UV/chlorine processes, including (c) 2,6-DCBQ, (d) TCBQ with the presence of TBA in the UV/chlorine process. ([HBQs]₀ = 20 μM, [HClO]₀ = 100 μM, pH= 7.0, UV= 3.9 × 10⁻⁶ Einstein/(L·s)).

Fig.2 Formation of chloroform from (a) 2,6-DCBQ and (b) TCBQ at different pHs by chlorine and UV/chlorine processes. ([HBQ]₀ = 20 μM, [HClO]₀ = 100 μM, reaction time= 15 min, UV= 3.9 × 10⁻⁶ Einstein/(L·s)).

Fig.3 Peak area ratios of the OH-HBQ products and the initial HBQ of 2,6-DCBQ and TCBQ: (a) effect of different pHs without UV irradiation, and (b) effect of UV irradiance at pH 7.0. ([HBQ]₀ = 20 μM, reaction time= 15 min).

Fig.4 Formation of (a) CHBr₂Cl and CHBr₃, (b) CHBrCl₂ and CHCl₃ from 2,6-DCBQ with the presence of bromide by chlorine and UV/chlorine processes. ([2,6-DCBQ]₀ = 20 μM, [HClO]₀ = 100 μM, [Br^-]₀ = 100 μM, pH= 7.0, UV= 3.9 × 10⁻⁶ Einstein/(L·s)).

Fig.5 Formation of (a) CHBr₂Cl and CHBr₃, (b) CHBrCl₂ and CHCl₃ from TCBQ with the presence of bromide by chlorine and UV/chlorine processes. ([TCBQs]₀ = 20 μM, [HClO]₀ = 100 μM, [Br^?]₀ = 100 μM, pH= 7.0, UV= 3.9 × 10⁻⁶ Einstein/(L·s)).

Fig.6 The (a) formation of CHBr₃ from 2,6-DCBQ, and (b) formation of CHBr₂Cl from TCBQ with the presence of bromide by chlorine and UV/chlorine processes at different pHs. ([HBQ]₀ = 20 μM, [HClO]₀ = 100 μM, [Br^-]₀ = 100 μM, reaction time= 15 min, UV= 3.9 × 10⁻⁶ Einstein/(L·s)).

Tab.1 The global nucleophilicity index and global electrophilicity index of HBQs and intermediates

Fig.7 Prediction of chlorination reactive sites on HBQs and intermediates by the local nucleophilicity index (N_k, e*eV) calculation (The N_k index is visualized by the diameter of red circles, a bigger red circle indicating a higher N_k index). (a) 2,6-DCBQ, (b) OH-DCBQ, (c) 2,6-DCBQ*, (d) OH-DCBQ*, (e) TCBQ, (f) OH-TCBQ, (g) TCBQ* and (h) OH-TCBQ*.

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