CAS OpenIR  > 湿法冶金清洁生产技术国家工程实验室
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
Source PublicationWATER RESEARCH
ISSN0043-1354
Volume122Pages:299-307
Abstract

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.

KeywordDisinfection Byproducts (Dbps) Halobenzoquinone (Hbq) Amino Acids Nucleophilic Reaction Covalent Binding Toxicity
SubtypeArticle
WOS HeadingsScience & Technology ; Technology ; Life Sciences & Biomedicine ; Physical Sciences
DOI10.1016/j.watres.2017.06.007
Indexed BySCI
Language英语
WOS KeywordDisinfection By-products ; Drinking-water ; Humic Constituents ; Bromo-benzoquinones ; Laccase Catalysis ; Quinones ; Stability ; Oxidation ; Chlorophenols ; Glutathione
WOS Research AreaEngineering ; Environmental Sciences & Ecology ; Water Resources
WOS SubjectEngineering, Environmental ; Environmental Sciences ; Water Resources
Funding OrganizationNational Natural Science Foundation of China(51378487 ; Youth Innovation Promotion Association, CAS(2014037) ; China Scholarship Council ; 51425405)
WOS IDWOS:000407404300030
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/23146
Collection湿法冶金清洁生产技术国家工程实验室
Affiliation1.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
Recommended Citation
GB/T 7714
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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