Electrochimica Acta p. 287 - 294 (2013)
Update date:2022-08-11
Topics:
Chan, Ya Yun
Yue, Yanni
Li, Yongxin
Webster, Richard D.
The electrochemical behavior of bisphenol A (BPA) was examined using cyclic voltammetry, bulk electrolysis and chemical oxidation in aprotic organic solvents. It was found that BPA undergoes a chemically irreversible voltammetric oxidation process to form compounds that cannot be electrochemically converted back to the starting materials on the voltammetric timescale. To overcome the effects of electrode fouling during controlled potential electrolysis experiments, NO+ was used as a one-electron chemical oxidant. A new product, hydroxylated bisdienone was isolated from the chemical oxidation of BPA with 4 mol equiv of NO+SbF6- in low water content CH3CN. The structure of the cation intermediate species was deduced and it was proposed that BPA is oxidized in a four-electron/two-proton process to form a relatively unstable dication which reacts quickly in the presence of water in acetonitrile (in a mechanism that is similar to phenols in general). However, as the water content of the solvent increased it was found that the chemical oxidation mechanism produced a nitration product in high yield. The findings from this study provide useful insights into the reactions that can occur during oxidative metabolism of BPA and highlight the possibility of the role of a bisdienone cation as a reactive metabolite in biological systems.
View MoreContact:86-571-85586718
Address:join hands science park,NO.4028 nanhuan road,hanghzou ,zhejiang,china
Contact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Hunan Haili Chemical Industry Co.,Ltd.
Contact:+86-731-85521860
Address:No.251, 2nd Section, Furong Road, Changsha,Hunan,China
Shanghai Maxchemco Chemical Industry Co., Ltd.
Contact:(86)21-51079223
Address:No.1305-8, B241, the Ecust Park, Huajing Road, Xuhui District, Shanghai
zhenjiang runjing high purity chemical co ltd
Contact:+86-511-83361155
Address:No.8.haixi road,international chemical park
Doi:10.3390/molecules23020375
(2018)Doi:10.1021/ol302006b
(2012)Doi:10.1021/j150318a010
(1930)Doi:10.1016/S0040-4039(00)95759-9
(1987)Doi:10.1039/c5sc00305a
(2015)Doi:10.3390/70800674
(2002)