Hydrolysis and Chlorination of 2,6-Dichloro-1,4-benzoquinone under conditions typical of drinking water distribution systems

Water Res. 2021 Jul 15:200:117219. doi: 10.1016/j.watres.2021.117219. Epub 2021 May 9.

Abstract

Halobenzoquinones (HBQs) are emerging disinfection by-products (DBPs) that are postulated drivers of bladder carcinogenicity. Prior assessments of 2,6-dichloro-1,4-benzoquinone (DCBQ) occurrence in drinking water distribution systems have revealed a gradual decline with increasing distance from points of entry. While this signals a degradation pathway, there is limited quantitative data on rate of that degradation. A systematic evaluation of DCBQ hydrolysis was performed, resulting in a rate law that is first order in both hydroxide [OH-] and [DCBQ]. The impact of temperature on that rate was characterized according to the Arrhenius relationship. Under the conditions tested (pH~7.2, T = 20°C) chloramine did not significantly impact DCBQ concentrations. However, DCBQ was rapidly degraded in solutions containing free available chlorine (FAC). Kinetic analysis showed non-integer order with respect to FAC. Further investigation led to a model that invoked reaction with dichlorine monoxide (Cl2O) as well as FAC.

Keywords: Disinfection by- products; Distribution system; Halobenzoquinones; Kinetics; Stability; Temperature.

MeSH terms

  • Benzoquinones
  • Chlorine
  • Disinfection
  • Drinking Water*
  • Halogenation
  • Hydrolysis
  • Kinetics
  • Water Pollutants, Chemical* / analysis
  • Water Purification*

Substances

  • Benzoquinones
  • Drinking Water
  • Water Pollutants, Chemical
  • Chlorine