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

Research on Chemical Intermediates - Tập 35 - Trang 21-34 - 2009
Julie R. Peller1, Stephen P. Mezyk2, William J. Cooper3
1Department of Chemistry, Indiana University Northwest, Gary, USA
2Department of Chemistry and Biochemistry, California State University at Long Beach, Long Beach, USA
3Urban Water Research Center, Department of Civil and Environmental Engineering, University of California, Irvine, Irvine, USA

Tóm tắt

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 × 109 (±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 μmol/kGy, corresponding to an overall degradation efficiency of 76%.

Tài liệu tham khảo

R.A. Rudel, S.J. Melly, P.W. Geno, G. Sun, J.G. Brody, Identification of alkylphenols and other estrogenic phenolic compounds in wastewater, septage, and groundwater on Cape Cod, Massachusetts. Environ. Sci. Technol. 32, 861–869 (1998) H.M. Kuch, K. Ballschmiter, Determination of endocrine-disrupting phenolic compounds and estrogens in surface and drinking water by HRGC-(NCI)-MS in the picogram per liter range. Environ. Sci. Technol. 35, 3201–3206 (2001) M. Furhacker, S. Scharf, H. Weber, Bisphenol A: emissions from point sources. Chemosphere 41, 751–756 (2000) H. Fromme, T. Kuchler, T. Otto, K. Pilz, J. Muller, A. Wenzel, Occurrence of phthalates and bisphenol A and F in the environment. Water Res. 36, 1429–1438 (2002) T. Suzuki, Y. Nakagawa, I. Takano, K. Yaguchi, Y. Kazuo, Environmental fate of bisphenol A and its biological metabolites in river water and their xeno-estrogenic activity. Environ. Sci. Technol. 38, 2389–2396 (2004) R. Bannister, N. Beresford, D. May, E.J. Routledge, S. Jobling, M. Rand-Weaver, Novel estrogen receptor-related transcripts in Marisa cornuarietis; a freshwater snail with reported sensitivity to estrogenic chemicals. Environ. Sci. Technol. 41, 2643–2650 (2007) S. Jobling, M. Nolan, C. Tyler, G. Brighty, J.P. Sumpter, Widespread secual disruption in wild fish. Environ. Sci. Technol. 32, 2498–2506 (1998) L.N. Vandenberg, M.V. Maffini, P.R. Wadia, C. Sonnenschein, B.S. Rubin, A.M. Soto, Exposure to environmentally relevant doses of the xenoestrogen bisphenol-A alters development of the fetal mouse mammary gland. Endocrinology 148, 116–127 (2007) K. Nakamura, K. Itoh, T. Sugimoto, S. Fushiki, Prenatal exposure to bisphenol A affects adult murine neocortical structure. Neurosci. Lett. 420, 100–105 (2007) Y. Takai, O. Tsutsumi, Y. Ikezuki, Y. Kamei, Y. Osuga, T. Yano, Y. Taketan, Preimplantation exposure to bisphenol A advances postnatal development. Reprod. Toxicol. 15, 71–74 (2001) I. Bautista-Toledo, M.A. Ferro-Garcia, J. Rivera-Utrilla, C. Moreno-Castilla, F.J. Vegas Fernandez, Bisphenol A removal from water by activated carbon. Effects of carbon characteristics and solution chemistry. Environ. Sci. Technol. 39, 6246–6250 (2005) G. Belgin, M.A. Oturan, N. Oturan, O. Erbatur, Indirect electrochemical treatment of bisphenol A in water via electrochemically generated Fenton’s reagent. Environ. Sci. Technol. 37, 3716–3723 (2003) Q. Huang, J. Weber, Transformation and removal of bisphenol A from aqueous phase via peroxidase-mediated oxidative coupling reactions: efficacy, products, and pathways. Environ. Sci. Technol. 39, 6029–6036 (2005) K. Nomiyama, T. Tanizaki, T. Koga, K. Arizono, R. Shinohara, Oxidative degradation of BPA using TiO2 in water, and transition of estrogenic activity in the degradation pathways. Arch. Environ. Contam. Toxicol. 52, 8–15 (2007) R. Thiruvenkatachari, T.O. Kwon, S. Moon, Application of slurry type photocatalytic oxidation-submerged hollow fiber microfiltration hybrid system for the degradation of bisphenol A (BPA). Sep. Sci. Technol. 40, 2871–2888 (2005) Y. Ohko, I. Ando, C. Niwa, T. Tatsuma, T. Yamamura, Y. Kubota, A. Fujishima, Degradation of bisphenol A in water by TiO2 photocatalyst. Environ. Sci. Technol. 35, 2365–2368 (2001) R.A. Torres, C. Petrier, E. Combat, F. Moulet, C. Pulgarin, Bisphenol A mineralization by integrated ultrasound-UV-iron (II) treatment. Environ. Sci. Technol. 41, 297–302 (2007) M. Deborde, S. Rabouan, J.-P. Duguet, B. Legube, Kinetics of aqueous ozone-induced oxidation of some endocrine disruptors. Environ. Sci. Technol. 39, 6086–6092 (2005) T. Saito, K. Kato, Y. Yokogawa, M. Nishida, N. Yamashita, Detoxification of bisphenol A and nonylphenol by purified extracellular laccase from a fungus isolated from soil. J. Biosci. Bioeng. 98, 64–66 (2004) G. Buxton, C. Greenstock, W.P. Helman, A.B. Ross, Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O−) in aqueous solution. J. Phys. Chem. Ref. Data 17, 513–886 (1988) J. Peller, P.V. Kamat, Radiolytic transformations of chlorinated phenols and chlorinated phenoxyacetic acids. J. Phys. Chem. A 109, 9528–9535 (2005) M.J. Lundqvist, L.A. Eriksson, Hydroxyl radical reactions with phenol as a model for generation of biologically reactive tyrosyl radicals. J. Phys. Chem. B 104, 848–855 (2000) U. Stafford, K. Gray, P.V. Kamat, Radiolytic and TiO2-assisted photocatalytic degradation of 4-chlorophenol. A comparative study. J. Phys. Chem. 98, 6343–6351 (1994) R. Terzian, N. Serpone, Pulse radiolytic studies of the reaction of pentahalophenols with OH radicals: formation of pentahalophenoxyl, dihydroxylpentahalocyclohexadienyl, and semiquinone radicals. Langmuir 7, 3081–3089 (1991) K. Whitham, S. Lyons, R. Miller, D. Nett, P. Treas, A. Zante, R.W. Fessenden, M.D. Thomas, Y. Wang, Linear accelerator for radiation chemistry research at Notre Dame in IEEE Proceedings of the Particle Accelerator Conference and International Conference on High Energy Accelerators, Dallas, Texas, 1995, pp. 131–133 G.V. Buxton, C.R. Stuart, Re-evaluation of the thiocyanate dosimeter for pulse radiolysis. J. Chem. Soc. Faraday Trans. 91, 279 (1995) S.P. Mezyk, T. Neubauer, W.J. Cooper, J.R. Peller, Free-radical-induced oxidative and reductive degradation of sulfa drugs in water: absolute kinetics and efficiencies of hydroxyl radical and hydrated electron reactions. J. Phys. Chem. A 111, 9019–9024 (2007) G. Albarran, J. Bentley, R.H. Schuler, Substituent effects in the reaction of OH radicals with aromatics: toluene. J. Phys. Chem.A 107, 7770–7774 (2003) M. Al-Sheikhly, J. Silverman, P. Neta, L. Karam, Mechanisms of ionizing radiation-induced destruction of 2,6-dichlorophenyl in aqueous solutions. Environ. Sci. Technol. 31, 2473–2477 (1997) B. Gozmen, M.A. Oturan, O. Oturan, O. Erbatur, Indirect electrochemical treatment of bisphenol A in water via electrochemically generated Fenton’s reagent. Environ. Sci. Technol. 37, 3716–3723 (2003) M. Roder, L. Wojnarovits, G. Foldiak, S.S. Emmi, G. Beggiato, M. D’Angelantonio, Addition and elimination kinetics in OH radical induced oxidation of phenol and cresols in acidic and alkaline solutions. Radiat. Phys. Chem. 54, 475–479 (1999) N.V. Raghavan, S. Steenken, Electrophilic reaction of the OH radical with phenol. Determination of the distribution of isomeric dihydroxycyclohexadienyl radicals. J. Am. Chem. Soc. 102, 3495–3499 (1980) G. Buxton, J.R. Langan, J.R. Smith, Aromatic hydroxylation. 8. A radiation chemistry study of the oxidation of hydroxycyclohexadienyl radicals. J Phys. Chem. 90, 6309–6313 (1986)