Abstract
In recent decades, increasing attention has been directed toward the effects of bisphenol A(BPA) as an environmental pollutant, primarily due to its demonstrated endocrine-disruptive effects. A growing body of evidence indicates that many BPA derivatives exhibit endocrine activity and other adverse biological properties. A review of the published literature was performed to identify BPA degradation intermediates resulting from chemical degradation processes of BPA, as well as its associated co-pollutants.Products of biological metabolism were not included in this study. Seventy-nine chemicals were identified. Of these chemicals, a subset - those containing two 6-membered aromatic rings connected by a central ring-linking carbon - was identified, anda further literature review was conducted to identify demonstrated biological effects associated with the chemicals in this subset. The objectives of this review were to assess the potential risks to human and environmental health associated with BPA derivatives,characterize our current understanding of BPA's degradation intermediates and copollutants,and identify compounds of interest that have received insufficient scrutiny.Laboratory experiments were performed on one of the BPA analogues identified in the literature review to better understand its degradation by photochemical processes. 4-cumylphenol (4-CP) is an impurity in industrial grade BPA, and has been identified in various environmental matrices. A series of experiments was conducted to determine the influence of variables including pH, and concentrations of chloride, humic acids (HA),carbonate, and nitrate on photo-oxidative processes under simulated sunlight in an artificial seawater matrix. 4-CP was shown to undergo both direct and indirect photodegradation in aqueous solutions. In the range of pH 6.0-9.0, higher pH was correlated with faster photodegradation rates both in the presence and absence of HA. Selective quenching of hydroxyl radical (•OH) by methanol served to identify reactions in which •OH plays a significant role. HA were shown to be an effective photosensitizer for the photodegradation of 4-CP. In the presence of NaCl, degradation is influenced by HA and nitrate, both of which act as photosensitizers in marine systems, and a synergistic effect was found to exist between HA and carbonate. Low concentrations of NaCl in the presence of HA inhibited photodegradation of 4-CP, but concentrations approaching and exceeding marine NaCl concentrations accelerated loss of 4-CP. Further work todetermine intermediates and products by mass spectroscopy will aid in understandingreaction mechanisms.