Radical/radical vs radical/molecule reactions in the formation of PCDD/Fs from (chloro)phenols in incinerators

Chemosphere. 2002 Mar;46(9-10):1273-8. doi: 10.1016/s0045-6535(01)00272-7.

Abstract

Pathways from chlorinated phenols as precursors to PCDD/Fs are discussed with focus on the effect of (poly)chlorination on thermochemistry and rate in the displacement of chlorine from a chlorophenol molecule by a (chloro)phenoxy radical (reaction (A) as a key example). Through measurements on the respective methylethers (anisoles) the O-H bond of 2,4,6-TCP turns out to be 5 kcal/ mol, and that in PCP 4 kcal/mol, less strong than O-H in phenol itself. On this basis it is concluded that-in contrast with earlier proposals--displacements such as in reaction (A) are at least as slow as reaction (B) of phenoxy radical with chlorobenzene. PhO. + PhCl -->PhOPh + Cl. reaction B Compared with condensation of two (chloro)phenoxy radicals, such radical/molecule reactions are therefore an insignificant pathway to dioxins in incinerators.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / analysis
  • Benzofurans / chemistry*
  • Dibenzofurans, Polychlorinated
  • Environmental Monitoring
  • Incineration
  • Polychlorinated Dibenzodioxins / analogs & derivatives*
  • Polychlorinated Dibenzodioxins / analysis
  • Polychlorinated Dibenzodioxins / chemistry*
  • Refuse Disposal*
  • Soil Pollutants / analysis*
  • Temperature

Substances

  • Benzofurans
  • Dibenzofurans, Polychlorinated
  • Polychlorinated Dibenzodioxins
  • Soil Pollutants