Electrophilic Chlorination of Naphthalene in Combustion Flue Gas

doi:10.1021/acs.est.9b00350

	Electrophilic Chlorination of Naphthalene in Combustion Flue Gas
	Wang, Dan 1,2; Zhang, Haijun 1; Fan, Yun 1; Ren, Meihui 1,2; Cao, Rong 1,2; Chen, Jiping 1
刊名	ENVIRONMENTAL SCIENCE & TECHNOLOGY
	2019-05-21
卷号	53 期号:10 页码:5741-5749
ISSN号	0013-936X
DOI	10.1021/acs.est.9b00350
通讯作者	Zhang, Haijun(hjzhang@dicp.ac.cn)
英文摘要	Naphthalene chlorination is an important formation mechanism of polychlorinated naphthalenes (PCNs) in combustion flue gas. In this study, a total of 21 metal chlorides and oxides were screened for their activities in the electrophilic chlorination of naphthalene. Copper(II) chloride exhibited the highest activity at 200-350 degrees C, followed by copper(I) chloride. Copper(II) chloride primarily acted as a strong chlorinating agent to facilitate chlorine substitution on naphthalene. Iron (II and III) chlorides were only highly active at 200-250 degrees C. At 250 degrees C, the average naphthalene chlorination efficiency over CuCl2 center dot 2H(2)O was 7.5-fold, 30.2-fold and 34.7-fold higher than those over CuCl, FeCl3 center dot 6H(2)O and FeCl2 center dot 4H(2)O, respectively. The other metal chlorides were less active. Under heated conditions, copper(II) and iron(III) chlorides were transformed to copper (I) and iron(II) chlorides via dechlorination, and then transformed to oxychlorides and oxides, thereby forming dechlorination-oxychlorination cycles of copper and iron species, respectively. The results obtained suggest that electrophilic chlorination of naphthalene in combustion flue gas is primarily driven by dechlorination-oxychlorination cycles of copper and iron species, and the reaction produces a selective chlorination pattern at 1 and 4 positions of naphthalene.
资助项目	National Natural Science Foundation of China[21876170] ; National Natural Science Foundation of China[21477125] ; Chinese National Basic Research Program[2015CB453100] ; Scientific Innovation Foundation[DICP ZZBS201601]
WOS关键词	DE-NOVO SYNTHESIS ; MSWI FLY-ASH ; POLYCYCLIC AROMATIC-HYDROCARBONS ; DIBENZO-P-DIOXINS ; POLYCHLORINATED NAPHTHALENES ; COPPER(II) CHLORIDE ; ORGANIC POLLUTANTS ; EMISSION ; PCNS ; SUBSTITUTION
WOS研究方向	Engineering ; Environmental Sciences & Ecology
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000469288100025
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese National Basic Research Program ; Chinese National Basic Research Program ; Scientific Innovation Foundation ; Scientific Innovation Foundation ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese National Basic Research Program ; Chinese National Basic Research Program ; Scientific Innovation Foundation ; Scientific Innovation Foundation ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese National Basic Research Program ; Chinese National Basic Research Program ; Scientific Innovation Foundation ; Scientific Innovation Foundation ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Chinese National Basic Research Program ; Chinese National Basic Research Program ; Scientific Innovation Foundation ; Scientific Innovation Foundation
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/172040]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Zhang, Haijun
作者单位	1.Chinese Acad Sci, CAS Key Lab Separat Sci Analyt Chem, Dalian Inst Chem Phys, Dalian 116023, Liaoning, Peoples R China 2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Wang, Dan,Zhang, Haijun,Fan, Yun,et al. Electrophilic Chlorination of Naphthalene in Combustion Flue Gas[J]. ENVIRONMENTAL SCIENCE & TECHNOLOGY,2019,53(10):5741-5749.
APA	Wang, Dan,Zhang, Haijun,Fan, Yun,Ren, Meihui,Cao, Rong,&Chen, Jiping.(2019).Electrophilic Chlorination of Naphthalene in Combustion Flue Gas.ENVIRONMENTAL SCIENCE & TECHNOLOGY,53(10),5741-5749.
MLA	Wang, Dan,et al."Electrophilic Chlorination of Naphthalene in Combustion Flue Gas".ENVIRONMENTAL SCIENCE & TECHNOLOGY 53.10(2019):5741-5749.