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http://dx.doi.org/10.4491/eer.2006.11.4.232

POLYCHLORINATED NAPHTHALENE (PCN) AND DIBENZOFURAN (PCDF) CONGENER PATTERNS FROM PHENOL PRECURSORS IN THERMAL PROCESS: [II] EXPERIMENTAL RESULTS FROM DICHLOROPHENOLS (DCPs)  

Ryu, Jae-Yong (Environmental Research Team, Daegu-Gyeongbuk Development Institute)
Kim, Do-Hyong (Environmental Engineering, Georgia Institute of Technology)
Choi, Kum-Chan (Department of Environmental Engineering, Dong-A University)
Suh, Jeong-Min (Department of Regional Environmental System Engineering, Pusan National University)
Publication Information
Environmental Engineering Research / v.11, no.4, 2006 , pp. 232-240 More about this Journal
Abstract
Polychlorinated naphthalenes (PCNs) formed along with dibenzo-p-dioxin and dibenzofuran products in the slow combustion of dichlorophenols (DCPs) at $600^{\circ}C$ were identified. Each DCP reactant produced a unique set of PCN products. Major PCN congeners observed in the experiments were consistent with products predicted from a mechanism involving an intermediate formed by ortho-ortho carbon coupling of phenoxy radicals; polychlorinated dibenzofurans (PCDFs) are formed from the same interemediate. Tautomerization of the intermediate and $H_2O$ elimination produces PCDFs; alternatively, CO elimination to form dihydrofulvalene and fusion produces naphthalenes. Only trace amounts of tetrachloronaphthalene congeners were formed, suggesting that the preferred PCN formation pathways from chlorinated phenols involve loss of chlorine. 3,4-DCP produced the largest yields of PCDF and PCN products with two or more chlorine substituents. 2,6-DCP did not produce tri- or tetra-chlorinated PCDF or PCN congeners. It did produce 1,8-DCN, however, which could not be explained.
Keywords
Municipal waste incinerator; Thermal process; Combustion; Polychlorinated Naphthalenes; Polychlorinated Dibenzofurans; Chlorophenol;
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