Bisphenol A reactions with hydroxyl radicals: diverse pathways determined between deionized water and tertiary treated wastewater solutions

Abstract

The oxidative reactions of bisphenol A (BPA) with radiolytically generated hydroxyl radicals were studied in both deionized water and tertiary treated wastewaters. In deionized water, bisphenol A reacts with the hydroxyl radical by addition to the aromatic ring, k = 6.9 9 10 9 (±0.2) M -1 s -1 , to eventually form the prominent, long-lived, hydroxylated intermediate product. In contrast, in tertiary treated water solutions, although the initial hydroxyl radical addition reaction occurs, the hydroxylation is averted, and a different mechanistic pathway ensues. The removal constant for the hydroxyl radical reaction with BPA is 0.45 ± 0.04 lmol/kGy, corresponding to an overall degradation efficiency of 76%.

Evaluation of parameters influencing removal efficiencies for organic contaminant degradation in advanced oxidation processes

“…While the reaction rate constant for the OH with BPA falls in the predicted range for aromatic compounds ((6.970.2) Â 10 9 M À1 s À1 ), the hydroxyl radical-mediated removal of BPA in high-purity water measured in steady state radiolysis experiments occurs with only 76% efficiency (Peller et al 2009). The removal efficiency is defined as the number of contaminant molecules destroyed per 100 hydroxyl radical reactions generated in solution.…”

“…For example, the initial step of OH reactions often involves addition to an electron-rich site. In the case of aromatic contaminants such as bisphenol A (BPA), the hydroxyl radical adds to an aromatic ring to form a transient cyclohexadienyl radical (as shown in Figure 1), which is readily detected using transient UV absorption (Peller et al 2009). The time-dependent changes in the transient absorption spectra provide insight into the subsequent chemistry that occurs.…”

“…The time-dependent changes in the transient absorption spectra provide insight into the subsequent chemistry that occurs. In a treated wastewater matrix, the initial OH reaction with BPA was followed by another fast chemical transformation, observed as the formation of a second transient absorption peak, which differed from its chemistry in pure water (Peller et al 2009). …”

Catalytic behavior of melamine glyoxal resin towards consecutive oxidation and oxy-Michael addition

“…The selectivities in DMF for cyclohexenol and cyclohexenone were found to be 37.19 and 62.81%, respectively. Analyses of insitu-generated peroxide in reaction media have been the area of major interest [24][25][26]. The starch iodide paper test was performed to check the presence of peroxide.…”

Hydroxy-Iron/β-cyclodextrin-Film Amperometric Sensor for the Endocrine Disruptor Substance Bisphenol-A in an Aqueous Medium with Reduced Fouling Effects

“…Currently, polycarbonates and epoxy resins are pervasively used to manufacture parts or bodies of various household and technological equipment such as supermarket food-wrappers, compact disks, soft drink bottles, electronic appliances, computers, furniture, auto-parts, machineries, and plastic pipes, to mention some (Burridge 2003;Saal and Hughes 2005). However, bisphenol A (BPA) possesses a similar partial chemical structure with the estrogen hormone, it exhibits affinity toward the estrogen receptor (Xu et al 2007), and has been identified as an endocrine disrupting chemical (Peller, Mezyk, and J. Cooper 2009). There is no doubt that BPA and its derivatives in the materials of the containers and wrappers of the food and drinks make their way into consumers' body fluid and the environment due to their high solubility in oils=fats and, to some extent, in water (Kuch and Ballschmiter 2001;Stuart et al 2005;NTP 2008).…”