Transformation of halobenzoquinones with the presence of amino acids in water: Products, pathways and toxicity
Du, Penghui1,2,3; Zhao, He1; Cao, Hongbin1; Huang, Ching-Hua3; Liu, Wen3; Li, Yao2
2017-10-01
发表期刊WATER RESEARCH
ISSN0043-1354
卷号122页码:299-307
摘要

The transformation and detoxification of halobenzoquinones (HBQs), a class of emerging disinfection byproducts (DBPs), was studied in the presence of amino acids (AAs). The reaction activity of three HBQs with Ms generally ranked as 2-chlorobenzoquinone (CBQ) < 2,6-dichlorobezoquinone (DCBQ) < tetrachloroquinone (TCBQ), consistent with their halogenation degree and the calculated electron affinity (EA) results. According to mass spectrometry and density functional theory (DFT) calculations, Ms can easily covalently incorporate into HBQs via nucleophilic addition (CBQ and DCBQ) or substitution (TCBQ) through C-N-C or C-S-C linkages. Hydroxylation, nucleophilic reaction and decarboxylation were proposed to be the three major reaction pathways for HBQs transformation with AAs. HBQs firstly underwent the spontaneous hydrolysis, resulting in OH-HBQs formation. Then, nucleophilic addition/substitution of AAs occurred on HBQs and OH-HBQs to produce AA-HBQs/AA-HBQs-OH adducts. These adducts were subsequently oxidized into their corresponding decarboxylated forms. Based on the results of Luminous bacterium Q67 acute toxicity test, the toxicity of HBQs solution greatly decreased with Ms presented. The toxicity change was well explained by the lowest unoccupied molecular orbital energy (E-LUMO) of formed products. Notably, the step that AAs nucleophilic bonded with HBQs led to the highest rise of k(LUMO), which should be the most effective pathway for HBQs detoxification. This study shows that binding with amino nitrogen compounds should be an important process for HBQs transformation and detoxification, which helps to better understand the fate of this typical DBP in surface water. (C) 2017 Elsevier Ltd. All rights reserved.

关键词Disinfection Byproducts (Dbps) Halobenzoquinone (Hbq) Amino Acids Nucleophilic Reaction Covalent Binding Toxicity
文章类型Article
WOS标题词Science & Technology ; Technology ; Life Sciences & Biomedicine ; Physical Sciences
DOI10.1016/j.watres.2017.06.007
收录类别SCI
语种英语
关键词[WOS]Disinfection By-products ; Drinking-water ; Humic Constituents ; Bromo-benzoquinones ; Laccase Catalysis ; Quinones ; Stability ; Oxidation ; Chlorophenols ; Glutathione
WOS研究方向Engineering ; Environmental Sciences & Ecology ; Water Resources
WOS类目Engineering, Environmental ; Environmental Sciences ; Water Resources
项目资助者National Natural Science Foundation of China(51378487 ; Youth Innovation Promotion Association, CAS(2014037) ; China Scholarship Council ; 51425405)
WOS记录号WOS:000407404300030
引用统计
被引频次:1[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.ipe.ac.cn/handle/122111/23146
专题湿法冶金清洁生产技术国家工程实验室
作者单位1.Chinese Acad Sci, Beijing Engn Res Ctr Proc Pollut Control, Inst Proc Engn, Div Environm Technol & Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Georgia Inst Technol, Sch Civil & Environm Engn, Atlanta, GA 30332 USA
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Du, Penghui,Zhao, He,Cao, Hongbin,et al. Transformation of halobenzoquinones with the presence of amino acids in water: Products, pathways and toxicity[J]. WATER RESEARCH,2017,122:299-307.
APA Du, Penghui,Zhao, He,Cao, Hongbin,Huang, Ching-Hua,Liu, Wen,&Li, Yao.(2017).Transformation of halobenzoquinones with the presence of amino acids in water: Products, pathways and toxicity.WATER RESEARCH,122,299-307.
MLA Du, Penghui,et al."Transformation of halobenzoquinones with the presence of amino acids in water: Products, pathways and toxicity".WATER RESEARCH 122(2017):299-307.
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