A quantum mechanical study on the formation of PCDD/Fs from 2-chlorophenol as precursor

Environ Sci Technol. 2008 Oct 1;42(19):7301-8. doi: 10.1021/es801599n.

Abstract

The most direct route to the formation of polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs) in combustion and thermal processes is the gas-phase reaction of chemical precursors such as chlorinated phenols. Detailed insight into the mechanism and kinetics properties is a prerequisite for understanding the formation of PCDD/Fs. In this paper, we carried out molecular orbital theory calculations for the homogeneous gas-phase formation of PCDD/Fs from 2-chlorophenol (2-CP). The profiles of the potential energy surface were constructed, and the possible formation pathways are discussed. The single-point energy calculation was carried out at the MPWB1K/ 6-311+G(3f,2p) level. Several energetically favorable formation pathways were revealed for the first time. The rate constants of crucial elementary steps were deduced over a wide temperature range of 600 approximately 1200 K using canonical variational transition-state theory (CVT) with small curvature tunneling contribution (SCT). The rate-temperature formulas were fitted. The ratio of PCDD to PCDF formed shows strong dependency on the reaction temperature and chlorophenoxy radicals (CPRs) concentration.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Chlorophenols / chemistry*
  • Dimerization
  • Kinetics
  • Polychlorinated Dibenzodioxins / analogs & derivatives*
  • Polychlorinated Dibenzodioxins / chemical synthesis
  • Polychlorinated Dibenzodioxins / chemistry
  • Quantum Theory*
  • Temperature

Substances

  • Benzofurans
  • Chlorophenols
  • Polychlorinated Dibenzodioxins
  • dibenzofuran