Chlorination of bisphenol A: kinetics and by-products formation

• Published in: Chemosphere (Oxford) Vol. 56; no. 5; pp. 465 - 473
• Main Authors: Gallard, Hervé, Leclercq, Amélie, Croué, Jean-Philippe
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 01.08.2004; Elsevier
• Subjects: Applied sciences; Benzhydryl Compounds; Bisphenol A; Chlorinated BPA congeners; Chlorination; Chlorine - chemistry; Chromatography, Gas; Chromatography, High Pressure Liquid; Drinking water and swimming-pool water. Desalination; Exact sciences and technology; Half-Life; Hydrogen-Ion Concentration; Kinetics; Models, Chemical; Phenols - chemistry; Pollution; Rate constants; Water Pollutants, Chemical - analysis; Water Supply - analysis; Water treatment and pollution; Bisphenol A; Chlorinated BPA congeners; Chlorination; Rate constants; Drinking water treatment; Organic matter; Chlorine; Reaction product; Pollutant formation; Disinfection; Endocrine disruptor; Operating conditions; Phenols; Kinetics
• ISSN: 0045-6535; 1879-1298
• DOI: 10.1016/j.chemosphere.2004.03.001

The kinetics of initial chlorination of bisphenol A (BPA) was studied between pH 2 and 11 at room temperature (20 ± 2 °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=3.10×10 4 M −1 s −1 for BPA − and 6.62 × 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.