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

Rachael F Lane; Craig D Adams; Stephen J Randtke; Ray E Carter Jr

doi:10.1016/j.watres.2015.04.014

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

Water Res. 2015 Aug 1:79:68-78. doi: 10.1016/j.watres.2015.04.014. Epub 2015 Apr 24.

Authors

Rachael F Lane¹, Craig D Adams², Stephen J Randtke³, Ray E Carter Jr³

Affiliations

¹ Department of Chemistry, University of Kansas, 2010 Malott Hall, 1251 Wescoe Drive, Lawrence, KS, 66045, United States.
² 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.
³ Department of Civil, Environmental, and Architectural Engineering, University of Kansas, 2150 Learned Hall, 1530 W. 15th St., Lawrence, KS, 66045, United States.

PMID: 25965889
DOI: 10.1016/j.watres.2015.04.014

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.

Keywords: Bisphenol A; Bisphenol A diglycidyl ether; Bisphenol F; Chlorination; Drinking water; Epoxy.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Benzhydryl Compounds / chemistry*
Chloramines / chemistry
Drinking Water / chemistry*
Endocrine Disruptors / chemistry*
Epoxy Compounds / chemistry*
Halogenation
Hydrogen-Ion Concentration
Kinetics
Phenols / chemistry*
Temperature
Water Pollutants, Chemical / chemistry*

Substances

Benzhydryl Compounds
Chloramines
Drinking Water
Endocrine Disruptors
Epoxy Compounds
Phenols
Water Pollutants, Chemical
2,2-bis(4-glycidyloxyphenyl)propane
chloramine
bisphenol A
4,4'-bisphenol F