title: Chlorination and chloramination of bisphenol A, bisphenol F, and bisphenol A diglycidyl ether in drinking water.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Drive, Lawrence, KS, 66045, United States.
authors.forename: Rachael F
authors.initials: RF
authors.lastname: Lane
authors.affiliation: Department of Civil and Environmental Engineering, Utah State University, 4110 Old Main Hill, EL 211D, Logan, UT, 84322-4110, United States. Electronic address: craig.adams@usu.edu.
authors.forename: Craig D
authors.initials: CD
authors.lastname: Adams
authors.affiliation: Department of Civil, Environmental, and Architectural Engineering, University of Kansas, 2150 Learned Hall, 1530 W. 15th St., Lawrence, KS, 66045, United States.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Randtke
authors.affiliation: Department of Civil, Environmental, and Architectural Engineering, University of Kansas, 2150 Learned Hall, 1530 W. 15th St., Lawrence, KS, 66045, United States.
authors.forename: Ray E
authors.initials: RE
authors.lastname: Carter
mesh_terms: D001559:Benzhydryl Compounds / Q000737:chemistry*; D002700:Chloramines / Q000737:chemistry; D060766:Drinking Water / Q000737:chemistry*; D052244:Endocrine Disruptors / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D054879:Halogenation; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D010636:Phenols / Q000737:chemistry*; D013696:Temperature; D014874:Water Pollutants, Chemical / Q000737:chemistry*; D000098826:Bisphenol A Compounds; D000098833:Bisphenol F Compounds
chemical_list: D001559:Benzhydryl Compounds; D002700:Chloramines; D060766:Drinking Water; D052244:Endocrine Disruptors; D004852:Epoxy Compounds; D010636:Phenols; D014874:Water Pollutants, Chemical; C019273:bisphenol A diglycidyl ether; D000098826:Bisphenol A Compounds; C030816:chloramine; C006780:bisphenol A; C008745:4,4'-bisphenol F; D000098833:Bisphenol F Compounds
keywords: Bisphenol A; Bisphenol A diglycidyl ether; Bisphenol F; Chlorination; Drinking water; Epoxy