Chlorination of bisphenol F and the estrogenic and peroxisome proliferator-activated receptor gamma effects of its disinfection byproducts. (15th December 2016)

• Record Type: Journal Article
• Authors: Zheng, Sai; Shi, Jia-chen; Hu, Jian-ying; Hu, Wen-xin; Zhang, Jing; Shao, Bing
• Is Part Of: Water research. Volume 107(2016)
• Page Start: 1
• Page End: 10
• Publication Date: 2016-12-15
• Subjects: Bisphenol F -- Chlorination -- Transformation byproducts -- Estrogenic effect -- Peroxisome proliferator-activated receptor gamma (PPAR-γ) effect; Water -- Pollution -- Research -- Periodicals; 363.7394
• DOI: 10.1016/j.watres.2016.10.048
• Languages: English
• ISSNs: 0043-1354

Abstract

Abstract: The reaction kinetics and transformation pathways between bisphenol F (BPF) and sodium hypochlorite were investigated at pH values ranging from 6.5 to 8.5 and with different initial concentration ratios. The reaction rate was pH- and free available chlorine (FAC)-dependent: the reaction rate at pH 8.5 was almost 10 times than that at pH 6.5. A total of 40 compounds were tentatively identified as chloro-substituted BPF and polyphenolic compounds by liquid chromatography quadrupole time-of-flight mass spectrometry operating in electrospray ionization mode (LC-ESI-Q-ToF), and 4 main byproducts were confirmed by 1 H and 13 C nuclear magnetic resonance (NMR). Toxicity tests indicated that the estrogenic effects of chloro-substituted BPF decrease as the chlorine substitution increase. On the contrary, increasing numbers of chlorines on the phenolic rings of BPF enhanced the nuclear receptor peroxisome proliferator-activated receptor gamma (PPARγ) activity. Tetra-chlorinated BPF had an approximately 6.9-fold higher activity than BPF. Graphical abstract: Highlights: Disinfection reaction rate was pH- and free available chlorine-dependent. About 40 byproducts were tentatively identified and reaction pathways were proposed. Estrogenic effects of byproducts decreased as the chlorine substitution increased. PPARγ effects of chlorine-substituted BPF were enhanced after chlorination.