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Int. J. Mol. Sci. 2015, 16(9), 20620-20640; doi:10.3390/ijms160920620

Quantum Chemical and Kinetic Study on Polychlorinated Naphthalene Formation from 3-Chlorophenol Precursor

Environment Research Institute, Shandong University, Jinan 250100, China
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Received: 31 July 2015 / Revised: 26 August 2015 / Accepted: 27 August 2015 / Published: 31 August 2015
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
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Abstract

Polychlorinated naphthalenes (PCNs) are the smallest chlorinated polycyclic aromatic hydrocarbons (Cl-PAHs) and are often called dioxin-like compounds. Chlorophenols (CPs) are important precursors of PCN formation. In this paper, mechanistic and kinetic studies on the homogeneous gas-phase formation mechanism of PCNs from 3-CP precursor were investigated theoretically by using the density functional theory (DFT) method and canonical variational transition-state theory (CVT) with small curvature tunneling contribution (SCT). The reaction priority of different PCN formation pathways were disscussed. The rate constants of crucial elementary steps were deduced over a wide temperature range of 600−1200 K. The mechanisms were compared with the experimental observation and our previous works on the PCN formation from 2-CP and 4-CP. This study shows that pathways ended with Cl elimination are favored over those ended with H elimination from the 3-CP precursor. The formation potential of MCN is larger than that of DCN. The chlorine substitution pattern of monochlorophenols has a significant effect on isomer patterns and formation potential of PCN products. The results can be input into the environmental PCN controlling and prediction models as detailed parameters, which can be used to confirm the formation routes of PCNs, reduce PCN emission and establish PCN controlling strategies. View Full-Text
Keywords: 3-chlorophenol; polychlorinated naphthalene; formation mechanism; rate constants; density functional method 3-chlorophenol; polychlorinated naphthalene; formation mechanism; rate constants; density functional method
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Xu, F.; Shi, X.; Zhang, Q. Quantum Chemical and Kinetic Study on Polychlorinated Naphthalene Formation from 3-Chlorophenol Precursor. Int. J. Mol. Sci. 2015, 16, 20620-20640.

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