Chlorination of bisphenol A: kinetics and by-products formation

Chemosphere. 2004 Aug;56(5):465-73. doi: 10.1016/j.chemosphere.2004.03.001.

Abstract

The kinetics of initial chlorination of bisphenol A (BPA) was studied between pH 2 and 11 at room temperature (20 +/- 2 degrees C). pH Profile of the apparent second-order rate constant of the reaction of BPA with chlorine were modeled considering the elementary reactions of HOCl with BPA species and an acid-catalyzed reaction. The predominant reactions at near neutral pH were the reactions of HOCl with the two phenolate species of BPA (k = 3.10 x 10(4) M(-1)s(-1) for BPA- and 6.62 x 10(4) M(-1) s(-1) for BPA(2-)). At near neutral pH, half-life times of BPA were calculated to be less than 1.5 h for chlorine residual higher than 0.2 mg l(-1). Chlorination of synthetic treated waters spiked with BPA showed that BPA disappeared within 4 h and that chlorinated bisphenol A congeners were rapidly formed and remained in solution for up to 10-20 h when low chlorine dosages are applied (0.5-1 mg l(-1)). To limit their presence in drinking water networks, it is then necessary to maintain high chlorine residuals that rapidly produce and decompose chlorinated bisphenol A congeners.

Publication types

  • Comparative Study

MeSH terms

  • Benzhydryl Compounds
  • Chlorine / chemistry*
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Half-Life
  • Hydrogen-Ion Concentration
  • Kinetics
  • Models, Chemical*
  • Phenols / chemistry*
  • Water Pollutants, Chemical / analysis*
  • Water Supply / analysis*

Substances

  • Benzhydryl Compounds
  • Phenols
  • Water Pollutants, Chemical
  • Chlorine
  • bisphenol A