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

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.

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.

Graphical abstract

Keywords

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

References

[1] Ben W, Sun P, Huang C H (2016). Effects of combined UV and chlorine treatment on chloroform formation from triclosan. Chemosphere, 150: 715–722

[2] Bull R J, Reckhow D A, Rotello V, Bull O M, Kim J (2006). Use of Toxicological and Chemical Models to Prioritize DBP Research. #2867., A.R.F.a.E.p. ed. Boston: Academic Press

[3] Cai M, Sun P, Zhang L, Huang C H (2017). UV/Peracetic Acid for Degradation of Pharmaceuticals and Reactive Species Evaluation. Environmental Science & Technology, 51(24): 14217–14224

[4] Chuang Y H, McCurry D L, Tung H H, Mitch W A (2015). Formation pathways and trade-offs between Haloacetamides and Haloacetaldehydes during combined chlorination and chloramination of lignin phenols and natural waters. Environmental Science & Technology, 49(24): 14432–14440

[5] Craik S A, Weldon D, Finch G R, Bolton J R, Belosevic M (2001). Inactivation of Cryptosporidium parvum oocysts using medium- and low-pressure ultraviolet radiation. Water Research, 35(6): 1387–1398

[6] Deng L, Huang C H, Wang Y L (2014). Effects of combined UV and chlorine treatment on the formation of trichloronitromethane from amine precursors. Environmental Science & Technology, 48(5): 2697–2705

[7] Michael C. Dodd and Ching-Hua Huang (2004). Transformation of the Antibacterial Agent Sulfamethoxazole in Reactions with Chlorine:  Kinetics, Mechanisms, and Pathways. Environmental Science & Technology, 38(21): 5607–5615 doi:10.1021/es035225z

[8] Dotson A D, Rodriguez C E, Linden K G (2012). UV disinfection implementation status in US water treatment plants. Journal AWWA, 104(5): E318–E324

[9] Du P, Zhao H, Cao H, Huang C H, Liu W, Li Y (2017). Transformation of halobenzoquinones with the presence of amino acids in water: Products, pathways and toxicity. Water Research, 122: 299–307

[10] Fang J, Fu Y, Shang C (2014). The roles of reactive species in micropollutant degradation in the UV/free chlorine system. Environmental Science & Technology, 48(3): 1859–1868

[11] Fang J Y, Shang C (2012). Bromate formation from bromide oxidation by the UV/persulfate process. Environmental Science & Technology, 46(16): 8976–8983

[12] Gao Z C, Lin Y L, Xu B, Xia Y, Hu C Y, Zhang T Y, Qian H, Cao T C, Gao N Y (2020). Effect of bromide and iodide on halogenated by-product formation from different organic precursors during UV/chlorine processes. Water Research, 182:116035

[13] Guo K, Wu Z, Shang C, Yao B, Hou S, Yang X, Song W, Fang J (2017). Radical chemistry and structural relationships of PPCP degradation by UV/Chlorine treatment in simulated drinking water. Environmental Science & Technology, 51(18): 10431–10439

[14] Hansen K M S, Zortea R, Piketty A, Vega S R, Andersen H R (2013). Photolytic removal of DBPs by medium pressure UV in swimming pool water. Science of the Total Environment, 443: 850–856

[15] Huang R, Wang W, Qian Y, Boyd J M, Zhao Y, Li X F (2013). Ultra pressure liquid chromatography-negative electrospray ionization mass spectrometry determination of twelve halobenzoquinones at ng/L levels in drinking water. Analytical Chemistry, 85(9): 4520–4529

[16] Li J, Wang W, Moe B, Wang H, Li X F (2015). Chemical and toxicological characterization of halobenzoquinones, an emerging class of disinfection byproducts. Chemical Research in Toxicology, 28(3): 306–318

[17] Li T, Jiang Y, An X, Liu H, Hu C, Qu J (2016). Transformation of humic acid and halogenated byproduct formation in UV-chlorine processes. Water Research, 102: 421–427

[18] Li X, Li Z, Xing Z, Song Z, Ye B, Wang Z, Wu Q (2021). UV-LED/P25-based photocatalysis for effective degradation of isothiazolone biocide. Frontiers of Environmental Science & Engineering, 15(5): 85 doi:10.1007/s11783-020-1379-x

[19] Lu T, Chen F (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry, 33(5): 580–592

[20] Mansor N A, Tay K S (2020). Potential toxic effects of chlorination and UV/chlorination in the treatment of hydrochlorothiazide in the water. Science of the Total Environment, 714: 136745

[21] Mellahi D, Zerdoumi R, Rebbani N, Gheid A (2015). The relationship between chlorine consumption and trihalomethane formation from hydrophobic and transphilic fractions: A comparative study between two dams of east Algeria. Journal of Water Reuse and Desalination, 5(1): 72–82

[22] Oliver B G, Carey J H (1977). Photochemical Production of Chlorinated Organics in Aqueous Solutions Containing Chlorine. Environmental Science & Technology, 11(9): 893–895

[23] Pan Y, Zhang X R, Zhai J P (2015). Whole pictures of halogenated disinfection byproducts in tap water from China’s cities. Frontiers of Environmental Science & Engineering, 9(1): 121–130

[24] Qian Y, Wang W, Boyd J M, Wu M, Hrudey S E, Li X F (2013). UV-induced transformation of four halobenzoquinones in drinking water. Environmental Science & Technology, 47(9): 4426–4433

[25] Qin F, Zhao Y Y, Zhao Y, Boyd J M, Zhou W, Li X F (2010). A toxic disinfection by-product, 2,6-dichloro-1,4-benzoquinone, identified in drinking water. Angewandte Chemie (International ed. in English), 49(4): 790–792

[26] Richardson S D, Ternes T A (2014). Water analysis: Emerging contaminants and current issues. Analytical Chemistry, 86(6): 2813–2848

[27] Saha A, Kawade M N, Upadhyaya H P, Kumar A, Naik P D (2013). Photoexcitation of 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane) to repulsive surface nσ*(C–Br) at 234 nm: Dynamics of C–Br and C–Cl bond rupture. Chemical Physics, 416: 1–10

[28] Sharma V K, Yang X, Cizmas L, Mcdonald T J, Luque R, Sayes C M, Yuan B L, Dionysiou D D (2017). Impact of metal ions, metal oxides, and nanoparticles on the formation of disinfection byproducts during chlorination. Chemical Engineering Journal, 317: 777–792

[29] Sharma V K, Yu X, McDonald T J, Jinadatha C, Dionysiou D D, Feng M (2019). Elimination of antibiotic resistance genes and control of horizontal transfer risk by UV-based treatment of drinking water: A mini review. Frontiers of Environmental Science & Engineering, 13(3): 37

[30] Shu Z, Li C, Belosevic M, Bolton J R, El-Din M G (2014). Application of a solar UV/chlorine advanced oxidation process to oil sands process-affected water remediation. Environmental Science & Technology, 48(16): 9692–9701

[31] Smith M B (2017). Organic Synthesis (4th Edition). Smith M B, ed. Boston: Academic Press, 97–160

[32] Sun P, Lee W N, Zhang R, Huang C H (2016). Degradation of DEET and Caffeine under UV/Chlorine and Simulated Sunlight/Chlorine Conditions. Environmental Science & Technology, 50(24): 13265–13273 doi:10.1021/acs.est.6b02287

[33] Wang W, Moe B, Li J H, Qian Y C, Zheng Q, Li X F (2016). Analytical characterization, occurrence, transformation, and removal of the emerging disinfection byproducts halobenzoquinones in water. Trends in Analytical Chemistry, 85: 97–110

[34] Wang W, Qian Y, Boyd J M, Wu M, Hrudey S E, Li X F (2013a). Halobenzoquinones in swimming pool waters and their formation from personal care products. Environmental Science & Technology, 47(7): 3275–3282

[35] Wang W, Qian Y, Boyd J M, Wu M, Hrudey S E, Li X F (2013b). Halobenzoquinones in swimming pool waters and their formation from personal care products. Environmental Science & Technology, 47(7): 3275–3282

[36] Wang W, Qian Y, Li J, Moe B, Huang R, Zhang H, Hrudey S E, Li X F (2014). Analytical and toxicity characterization of halo-hydroxyl-benzoquinones as stable halobenzoquinone disinfection byproducts in treated water. Analytical Chemistry, 86(10): 4982–4988

[37] Wang H, Ma D, Shi W,  Yang Z, Cai Y, Gao B (2021).  Formation of disinfection by-products during sodium hypochlorite cleaning of fouled membranes from membrane bioreactors. Frontiers of Environmental Science & Engineering, 15(5):  102 doi:10.1007/s11783-021-1389-3

[38] Westerhoff P, Chao P, Mash H (2004). Reactivity of natural organic matter with aqueous chlorine and bromine. Water Research, 38(6): 1502–1513

[39] Wu Q Y, Yan Y J, Lu Y, Du Y, Liang Z F, Hu H Y (2020). Identification of important precursors and theoretical toxicity evaluation of byproducts driving cytotoxicity and genotoxicity in chlorination. Frontiers of Environmental Science & Engineering, 14(2): 25

[40] Yang C, Sun W, Ao X (2020). Bacterial inactivation, DNA damage, and faster ATP degradation induced by ultraviolet disinfection. Frontiers of Environmental Science & Engineering, 14(1): 13

[41] Yang P, Kong D, Ji Y, Lu J, Yin X, Zhou Q (2018). Chlorination and chloramination of benzophenone-3 and benzophenone-4 UV filters. Ecotoxicology and Environmental Safety, 163: 528–535

[42] Young T R, Li W, Guo A, Korshin G V, Dodd M C (2018). Characterization of disinfection byproduct formation and associated changes to dissolved organic matter during solar photolysis of free available chlorine. Water Research, 146: 318–327

[43] Zhang K, Parker K M (2018). Halogen Radical Oxidants in Natural and Engineered Aquatic Systems. Environmental Science & Technology, 52(17): 9579–9594

[44] Zhang X, Wei D, Sun X, Bai C, Du Y (2021). Free available chlorine initiated Baeyer-Villiger oxidation: A key mechanism for chloroform formation during aqueous chlorination of benzophenone UV filters. Environmental Pollution, 268(Pt A): 115737

[45] Zhang Y S, Shao Y S, Gao N Y, Gao Y Q, Chu W H, Li S, Wang Y, Xu S X (2018). Kinetics and by-products formation of chloramphenicol (CAP) using chlorination and photocatalytic oxidation. Chemical Engineering Journal, 333: 85–91

[46] Zhao Q, Shang C, Zhang X, Ding G, Yang X (2011). Formation of halogenated organic byproducts during medium-pressure UV and chlorine coexposure of model compounds, NOM and bromide. Water Research, 45(19): 6545–6554

[47] Zhao Y, Anichina J, Lu X, Bull R J, Krasner S W, Hrudey S E, Li X F (2012). Occurrence and formation of chloro- and bromo-benzoquinones during drinking water disinfection. Water Research, 46(14): 4351–4360

[48] Zhao Y, Qin F, Boyd J M, Anichina J, Li X F (2010). Characterization and determination of chloro- and bromo-benzoquinones as new chlorination disinfection byproducts in drinking water. Analytical Chemistry, 82(11): 4599–4605

[49] Zhong C, Zhao H, Han Q, Cao H, Duan F, Shen J, Xie Y, Guo W, Sun S (2020). Coupling-oxidation process promoted ring-opening degradation of 2-mecapto-5-methyl-1,3,4-thiadizaole in wastewater. Water Research, 186: 116362 doi: 10.1016/j.watres.2020.116362

[50] Zhu Q, Gu A, Li D, Zhang T, Xiang L, He M (2021). Online recognition of drainage type based on UV-vis spectra and derivative neural network algorithm. Frontiers of Environmental Science & Engineering, 15(6): 136 doi:10.1007/s11783-021-1430-6

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.

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://doi.org/10.1007/s11783-021-1510-7 and is accessible for authorized users.

RIGHTS & PERMISSIONS

2021 Higher Education Press