Oxidative removal of quinclorac by permanganate through a rate-limiting [3+2] cycloaddition reaction

doi:10.1039/c8em00024g

CORC > 烟台海岸带研究所 > 中国科学院烟台海岸带研究所 > 中科院海岸带环境过程与生态修复重点实验室 > 近岸生态与环境实验室

	Oxidative removal of quinclorac by permanganate through a rate-limiting [3+2] cycloaddition reaction
	Song, Dean ; Cheng, Hanyang ; Jiang, Xiaohua ; Sun, Huiqing ; Kong, Fanyu ; Liang, Rongning ; Qiang, Zhimin ; Liu, Huijuan ; Qu, Jiuhui
刊名	ENVIRONMENTAL SCIENCE-PROCESSES & IMPACTS
	2018-05-01
卷号	20 期号:5 页码:790-797
关键词	TRANSFORMATION PRODUCTS REACTION-KINETICS POTASSIUM-PERMANGANATE LEPORINUS-OBTUSIDENS MASS-SPECTROMETRY WATER-TREATMENT BY-PRODUCTS DEGRADATION HERBICIDES CHLORINATION
ISSN号	2050-7887
DOI	10.1039/c8em00024g
产权排序	[Song, Dean ; Sun, Huiqing ; Kong, Fanyu] Chinese Acad Agr Sci, Tobacco Res Inst, State Agr Minist Lab Qual & Safety Risk Assessmen, Qingdao 266101, Peoples R China ; [Song, Dean ; Jiang, Xiaohua ; Liang, Rongning] Chinese Acad Sci, Yantai Inst Coastal Zone Res, Key Lab Coastal Environm Proc & Ecol Remediat, Yantai 264003, Peoples R China ; [Cheng, Hanyang ; Qiang, Zhimin ; Liu, Huijuan ; Qu, Jiuhui] Chinese Acad Sci, Res Ctr Ecoenvironm Sci, Key Lab Drinking Water Sci & Technol, Beijing 100085, Peoples R China
文献子类	Article
英文摘要	Quinclorac, a widely used herbicide in agriculture, has been recognized as an emerging environmental pollutant owing to its long persistence and potential risk to humans. However, no related information is available on the degradation of quinclorac by employing oxidants. Herein, the reactivity of quinclorac with permanganate was systematically investigated in water by combining experimental and computational approaches. The reaction followed overall second-order kinetics pointing to a bimolecular rate-limiting step. The second-order rate constant was found to be 3.47 10 3 M 1 s 1 at 25 C, which was independent of pH over the range from 5 to 9 and was dependent on temperature over the range from 19 to 35 C. The initial product was identified by UPLC-Q-TOF-MS to be monohydroxylated quinclorac, which was more susceptible to further oxidation. The result could be supported by the complete simulation of the reaction process in DFT calculations, indicating the [3 + 2] cycloaddition oxidation of the benzene ring in the rate-limiting step. The plausible mechanism was then proposed, accompanied by the analysis of the HOMO indicating the hydroxylation position and of the ESP suggesting a more electron-rich moiety. Considering the high effectiveness and low toxicity, permanganate oxidation was considered to be a very promising technique for removing quinclorac from aquatic environments.
WOS关键词	TRANSFORMATION PRODUCTS ; REACTION-KINETICS ; POTASSIUM-PERMANGANATE ; LEPORINUS-OBTUSIDENS ; MASS-SPECTROMETRY ; WATER-TREATMENT ; BY-PRODUCTS ; DEGRADATION ; HERBICIDES ; CHLORINATION
WOS研究方向	Chemistry, Analytical ; Environmental Sciences
语种	英语
WOS记录号	WOS:000433191900007
资助机构	Agricultural Science and Technology Innovation Program [ASTIPTRIC06] ; Science and Technology Project of Yantai [2014ZH086] ; Youth Innovation Promotion Association of CAS [2014190] ; National Natural Science Foundation of China [41576106] ; Qingdao Postdoctoral Application Research Project [2016105]
内容类型	期刊论文
源URL	[http://ir.yic.ac.cn/handle/133337/24472]
专题	烟台海岸带研究所_近岸生态与环境实验室烟台海岸带研究所_中科院海岸带环境过程与生态修复重点实验室
作者单位	1.Chinese Acad Sci, Res Ctr Ecoenvironm Sci, Key Lab Drinking Water Sci & Technol, Beijing 100085, Peoples R China 2.Chinese Acad Agr Sci, Tobacco Res Inst, State Agr Minist Lab Qual & Safety Risk Assessmen, Qingdao 266101, Peoples R China; 3.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Key Lab Coastal Environm Proc & Ecol Remediat, Yantai 264003, Peoples R China;
推荐引用方式 GB/T 7714	Song, Dean,Cheng, Hanyang,Jiang, Xiaohua,et al. Oxidative removal of quinclorac by permanganate through a rate-limiting [3+2] cycloaddition reaction[J]. ENVIRONMENTAL SCIENCE-PROCESSES & IMPACTS,2018,20(5):790-797.
APA	Song, Dean.,Cheng, Hanyang.,Jiang, Xiaohua.,Sun, Huiqing.,Kong, Fanyu.,...&Qu, Jiuhui.(2018).Oxidative removal of quinclorac by permanganate through a rate-limiting [3+2] cycloaddition reaction.ENVIRONMENTAL SCIENCE-PROCESSES & IMPACTS,20(5),790-797.
MLA	Song, Dean,et al."Oxidative removal of quinclorac by permanganate through a rate-limiting [3+2] cycloaddition reaction".ENVIRONMENTAL SCIENCE-PROCESSES & IMPACTS 20.5(2018):790-797.