DICP OpenIR
Electrophilic Chlorination of Naphthalene in Combustion Flue Gas
Wang, Dan1,2; Zhang, Haijun1; Fan, Yun1; Ren, Meihui1,2; Cao, Rong1,2; Chen, Jiping1
Corresponding AuthorZhang, Haijun(hjzhang@dicp.ac.cn)
Source PublicationENVIRONMENTAL SCIENCE & TECHNOLOGY
2019-05-21
ISSN0013-936X
DOI10.1021/acs.est.9b00350
Volume53Issue:10Pages:5741-5749
Funding ProjectNational Natural Science Foundation of China[21876170] ; National Natural Science Foundation of China[21477125] ; Chinese National Basic Research Program[2015CB453100] ; Scientific Innovation Foundation[DICP ZZBS201601]
Funding OrganizationNational 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
WOS SubjectEngineering, Environmental ; Environmental Sciences
WOS Research AreaEngineering ; Environmental Sciences & Ecology
WOS KeywordDE-NOVO SYNTHESIS ; MSWI FLY-ASH ; POLYCYCLIC AROMATIC-HYDROCARBONS ; DIBENZO-P-DIOXINS ; POLYCHLORINATED NAPHTHALENES ; COPPER(II) CHLORIDE ; ORGANIC POLLUTANTS ; EMISSION ; PCNS ; SUBSTITUTION
AbstractNaphthalene 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.
Language英语
Funding OrganizationNational 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
WOS IDWOS:000469288100025
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/172041
Collection中国科学院大连化学物理研究所
Corresponding AuthorZhang, Haijun
Affiliation1.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
Recommended Citation
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.
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