Chlorination and chloramination of bisphenol A, bisphenol F, and bisphenol A diglycidyl ether in drinking water

• BPA and BPF are oxidized by free chlorine (HOCl/OCl−) under drinking water conditions.
• Half-lives of BPA and BPF with 1 mg/L of free chlorine ranged from 3 to 35 min.
• BPA and BPF are oxidized by monochloramine (NH2Cl) under drinking water conditions.
• Half-lives of BPA and BPF with 3.5 mg/L NH2Cl as Cl2 were approximately 1–10 days.
• BADGE was found unreactive with both free chlorine and monochloramine.

Bisphenol A (BPA), bisphenol F (BPF), and bisphenol A diglycidyl ether (BADGE) are common components of epoxy coatings used in food packaging and in drinking water distribution systems. Thus, leachates from the epoxy may be exposed to the disinfectants free chlorine (Cl2/HOCl/OCl−) and monochloramine (MCA, NH2Cl). Bisphenols are known endocrine disrupting chemicals (EDC) with estrogenic activity. Chlorination by-products have the potential to have reduced or enhanced estrogenic qualities, and are, therefore, of interest. In this work, chlorination reactions for bisphenols and BADGE were explored (via LC/MS/MS) and kinetic modeling (using a pseudo-first order approach) was conducted to predict the fate of these compounds in drinking water. The half-lives of BPA and BPF with 1 mg/L of free chlorine ranged from 3 to 35 min over the pH range from 6 to 11 and the temperature range of 10–25 °C. Half-lives for reactions of BPA and BPF with a nominal MCA concentration of 3.5 mg/L as Cl2 were from 1 to 10 days and were greater at higher pH and lower temperature. Formation of chlorinated bisphenol A by-products was observed during the kinetic studies. BADGE was found unreactive with either oxidant.