Transformation, products, and pathways of chlorophenols via electro-enzymatic catalysis: How to control toxic intermediate products
Du, Penghui1,2; Zhao, He1; Li, Haitao3; Zhang, Di1; Huang, Ching-Hua4; Deng, Manfeng1; Liu, Chenming1; Cao, Hongbin1
2016-02-01
发表期刊CHEMOSPHERE
ISSN0045-6535
卷号144期号:FEB页码:1674-1681
摘要Chlorophenols can be easily oxidized into chlorobenzoquinones (CBQs), which are highly toxic and have been linked to bladder cancer risk. Herein, we report the transformation, products, and pathways of 2,4-dichlorophenol (DCP) by horseradish peroxidase (HRP) and electro-generated hydrogen peroxide (H2O2) and suggest methods to control the formation of toxic intermediate products. After a 10-min electroenzymatic process, 99.7% DCP removal may be achieved under optimal conditions. A total of 16 reaction products, most of which are subsequently verified as DCA polymers and related quinone derivatives, are identified by using ultra-performance liquid chromatography-time-of-flight mass spectrometry (UPLC-TOF-MS). A five-step reaction pathway for DCP transformation, including HRP-driven substrate oxidation, substitution and radical coupling, quick redox equilibrium, nucleophilic reaction and precipitation from aqueous solution, is proposed. Current variations and the presence of CO2 could significantly affect these reaction pathways. In particular, higher currents enhance the hydroxylation process by promoting alkaline conditions and abundant H2O2 formation. As both OH- and H2O2 are strong nucleophiles, they easily react with CBQ products to form hydroxylated products, which can significantly reduce solution toxicity. An adequate supply of CO2 can provide favorable pH conditions and facilitate enzymatic steps, such as substrate oxidation and radical coupling, to generate precipitable polymerized products. All of the results suggest that toxic intermediate products can be effectively reduced and controlled during the electroenzymatic process to remove DCP and other phenolic pollutants from wastewaters. (C) 2015 Elsevier Ltd. All rights reserved.
关键词Electro-enzymatic Catalysis 2 Horseradish Peroxidase (Hrp) 4-dichlorophenol Oxidative Coupling Reaction Mechanism
文章类型Article
WOS标题词Science & Technology ; Life Sciences & Biomedicine
DOI10.1016/j.chemosphere.2015.10.038
收录类别SCI
语种英语
关键词[WOS]IMMOBILIZED HORSERADISH-PEROXIDASE ; DISINFECTION BY-PRODUCTS ; LACCASE CATALYSIS ; BISPHENOL-A ; REMOVAL ; DEGRADATION ; PHENOLS ; WATER ; 2,4-DICHLOROPHENOL ; PENTACHLOROPHENOL
WOS研究方向Environmental Sciences & Ecology
WOS类目Environmental Sciences
项目资助者National Natural Science Foundation of China(51108441 ; 51209191 ; 51102238 ; 51378487)
WOS记录号WOS:000367774400212
引用统计
被引频次:6[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/122111/20262
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, Key Lab Green Proc & Engn, Beijing 100190, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Being Acad Sci & Technol, Environm Protect Inst Light Ind, Beijing 100089, Peoples R China
4.Georgia Inst Technol, Sch Civil & Environm Engn, Atlanta, GA 30332 USA
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Du, Penghui,Zhao, He,Li, Haitao,et al. Transformation, products, and pathways of chlorophenols via electro-enzymatic catalysis: How to control toxic intermediate products[J]. CHEMOSPHERE,2016,144(FEB):1674-1681.
APA Du, Penghui.,Zhao, He.,Li, Haitao.,Zhang, Di.,Huang, Ching-Hua.,...&Cao, Hongbin.(2016).Transformation, products, and pathways of chlorophenols via electro-enzymatic catalysis: How to control toxic intermediate products.CHEMOSPHERE,144(FEB),1674-1681.
MLA Du, Penghui,et al."Transformation, products, and pathways of chlorophenols via electro-enzymatic catalysis: How to control toxic intermediate products".CHEMOSPHERE 144.FEB(2016):1674-1681.
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