Oxidation of bisphenol A by a boron-doped diamond electrode in different water matrices: transformation products and inorganic by-products

Abstract

An electrochemical advanced oxidation process employing a boron-doped diamond anode for the treatment of synthetic waters and secondary effluents of wastewater treatment plants (WWTP) was studied. The efficiency and formation of transformation products (TPs) for this treatment process were investigated at different current densities for bisphenol A (BPA) spiked to synthetic water and WWTP effluents. A complete removal of the parent compound was achieved in WWTP effluents. Higher applied current densities resulted in faster removal. At the same time, a correlation between the applied current density and the ozone concentration measured in the bulk solution was revealed. Hence, the observed transformation of BPA is likely due to the generation of reactive oxygen species such as hydroxyl radicals and ozone. Based on a suspected target screening approach, four known TPs and two unreported (new) TPs were identified by LC–MS analysis. These results suggest a transformation pathway following three steps: hydroxylation of the aromatic ring, followed by oxidation of the isopropylidene bridge and finally a ring opening and formation of organic acids and other small molecules. The presence of chloride ions in WWTP effluents can result in the generation of excessive concentrations of chlorate and perchlorate during electrochemical oxidation. Applying a current density of 208 mA cm−2, a complete elimination of BPA was achievable after 15 min (Q/V = 430 mA h L−1); however, the oxidation resulted in concentrations of chlorate and perchlorate of 2.85 and 5.65 mg L−1, respectively. These values were directly dependent on the exposure time and desired degree of BPA removal.

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References

  1. Andreozzi R (1999) Advanced oxidation processes (AOP) for water purification and recovery. Catal Today 53:51–59

    CAS  Article  Google Scholar 

  2. Anglada A, Urtiaga A, Ortiz I, Mantzavinos D, Diamadopoulos E (2011) Boron-doped diamond anodic treatment of landfill leachate: evaluation of operating variables and formation of oxidation by-products. Water Res 45:828–838

    CAS  Article  Google Scholar 

  3. Arnold SM, Clark KE, Staples CA, Klecka GM, Dimond SS, Caspers N, Hentges SG (2013) Relevance of drinking water as a source of human exposure to bisphenol A. J Expo Sci Environ Epidemiol 23:137–144

    CAS  Article  Google Scholar 

  4. Arslan-Alaton I, Aytac E, Kusk KO (2014) Effect of Fenton treatment on the aquatic toxicity of bisphenol A in different water matrices. Environ Sci Pollut Res Int 21:12122–12128

    CAS  Article  Google Scholar 

  5. Azizi O, Hubler D, Schrader G, Farrell J, Chaplin BP (2011) Mechanism of perchlorate formation on boron-doped diamond film anodes. Environ Sci Technol 45:10582–10590

    CAS  Article  Google Scholar 

  6. Bader H, Hoigné J (1981) Determination of ozone in water by the indigo method. Water Res 15:449–456

    CAS  Article  Google Scholar 

  7. Bergmann MEH, Koparal AS, Iourtchouk T (2014) Electrochemical advanced oxidation processes, formation of halogenate and perhalogenate species—a critical review. Crit Rev Environ Sci Technol 44:348–390

    CAS  Article  Google Scholar 

  8. Bertanza G, Pedrazzani R, Zambarda V, Grande MD, Icarelli F, Baldassarre L (2010) Removal of endocrine disrupting compounds from wastewater treatment plant effluents by means of advanced oxidation. Water Sci Technol 61:1663–1671

    CAS  Article  Google Scholar 

  9. Bourgin M, Bichon E, Antignac JP, Monteau F, Leroy G, Barritaud L, Chachignon M, Ingrand V, Roche P, Le Bizec B (2013) Chlorination of bisphenol A: non-targeted screening for the identification of transformation products and assessment of estrogenicity in generated water. Chemosphere 93:2814–2822

    CAS  Article  Google Scholar 

  10. Brede C, Fjeldal P, Skjevrak I, Herikstad H (2003) Increased migration levels of bisphenol A from polycarbonate baby bottles after dishwashing, boiling and brushing. Food Addit Contam 20:684–689

    CAS  Article  Google Scholar 

  11. Cui YH, Li XY, Chen G (2009) Electrochemical degradation of bisphenol A on different anodes. Water Res 43:1968–1976

    CAS  Article  Google Scholar 

  12. Da Silva JCC, Reis Teodoro JA, Afonso RJ, Aquino SF, Augusti R (2014) Photodegradation of bisphenol A in aqueous medium: monitoring and identification of by-products by liquid chromatography coupled to high-resolution mass spectrometry. Rapid Commun Mass Spectrom 28:987–994

    Article  Google Scholar 

  13. Dupuis A, Migeot V, Cariot A, Albouy-Llaty M, Legube B, Rabouan S (2012) Quantification of bisphenol A, 353-nonylphenol and their chlorinated derivatives in drinking water treatment plants. Environ Sci Pollut Res Int 19:4193–4205

    CAS  Article  Google Scholar 

  14. Fujishima A, Einaga Y, Rao TN, Tryk DA (2005) Diamond electrochemistry. BKC, Tokyo, p 586

    Google Scholar 

  15. Gasperi J, Sebastian C, Ruban V, Delamain M, Percot S, Wiest L, Mirande C, Caupos E, Demare D, Kessoo M, Kessoo D, Saad M, Schwartz JJ, Dubois P, Fratta C, Wolff H, Moilleron R, Chebbo G, Cren C, Millet M, Barraud S, Gromaire MC (2014) Micropollutants in urban stormwater: occurrence, concentrations, and atmospheric contributions for a wide range of contaminants in three French catchments. Environ Sci Pollut Res Int 21:5267–5281

    CAS  Article  Google Scholar 

  16. Greco G, Grosse S, Letzel T (2013) Serial coupling of reversed-phase and zwitterionic hydrophilic interaction LC/MS for the analysis of polar and nonpolar phenols in wine. J Sep Sci 36:1379–1388

    CAS  Article  Google Scholar 

  17. Gültekin I, Ince NH (2007) Synthetic endocrine disruptors in the environment and water remediation by advanced oxidation processes. J Environ Manag 85:816–832

    Article  Google Scholar 

  18. Huber MM, Göbel A, Joss A, Hermann N, Löffler D, McArdell CS, Ried A, Siegrist H, Ternes TA, von Gunten U (2005) Oxidation of pharmaceuticals during ozonation of municipal wastewater effluents: a pilot study. Environ Sci Technol 39:4290–4299

    CAS  Article  Google Scholar 

  19. International Organization for Standardization (2007) Water quality—determination of dissolved anions by liquid chromatography of ions. International Organization for Standardization, Geneva, p 15

    Google Scholar 

  20. Ju P, Fan H, Guo D, Meng X, Xu M, Ai S (2012) Electrocatalytic degradation of bisphenol A in water on a Ti-based PbO2–ionic liquids (ILs) electrode. Chem Eng J 179:99–106

    CAS  Article  Google Scholar 

  21. Kraft A (2007) Doped diamond: a compact review on a new, versatile electrode material. Int J Electrochem Sci 2:355–385

    CAS  Google Scholar 

  22. Kraft A, Stadelmann M, Wünsche M, Blaschke M (2006) Electrochemical ozone production using diamond anodes and a solid polymer electrolyte. Electrochem Commun 8:883–886

    CAS  Article  Google Scholar 

  23. Krauss M, Singer H, Hollender J (2010) LC-high resolution MS in environmental analysis: from target screening to the identification of unknowns. Anal Bioanal Chem 397:943–951

    CAS  Article  Google Scholar 

  24. Kusvuran E, Yildirim D (2013) Degradation of bisphenol A by ozonation and determination of degradation intermediates by gas chromatography–mass spectrometry and liquid chromatography–mass spectrometry. Chem Eng J 220:6–14

    CAS  Article  Google Scholar 

  25. Lang IA, Galloway TS, Scarlett A, Henley WE, Depledge M, Wallace RB, Melzer D (2008) Association of urinary bisphenol A concentration with medical disorders and laboratory abnormalities in adults. JAMA 300:1303–1310

    CAS  Article  Google Scholar 

  26. Martínez-Huitle CA, Ferro S (2006) Electrochemical oxidation of organic pollutants for the wastewater treatment: direct and indirect processes. Chem Soc Rev 35:1324–1340

    Article  Google Scholar 

  27. May PW (2008) Materials science. The new diamond age? Science 319:1490–1491

    CAS  Article  Google Scholar 

  28. Molkenthin M, Olmez-Hanci T, Jekel MR, Arslan-Alaton I (2013) Photo-Fenton-like treatment of BPA: effect of UV light source and water matrix on toxicity and transformation products. Water Res 47:5052–5064

    CAS  Article  Google Scholar 

  29. Murugananthan M, Yoshihara S, Rakuma T, Shirakashi T (2008) Mineralization of bisphenol A (BPA) by anodic oxidation with boron-doped diamond (BDD) electrode. J Hazard Mater 154:213–220

    CAS  Article  Google Scholar 

  30. Oturan MA, Pinson J (1995) Hydroxylation by electrochemically generated OH radicals. Mono- and polyhydroxylation of benzoic acid: products and isomers distribution. J Phys Chem 99:13948–13954

    CAS  Article  Google Scholar 

  31. Panizza M, Cerisola G (2009) Direct and mediated anodic oxidation of organic pollutants. Chem Rev 109:6541–6569

    CAS  Article  Google Scholar 

  32. Pereira GF, Rocha-Filho RC, Bocchi N, Biaggio SR (2012) Electrochemical degradation of bisphenol A using a flow reactor with a boron-doped diamond anode. Chem Eng J 198–199:282–288

    Article  Google Scholar 

  33. Qiu L-L, Wang X, Zhang X-H, Zhang Z, Gu J, Liu L, Wang Y, Wang X, Wang S-L (2013) Decreased androgen receptor expression may contribute to spermatogenesis failure in rats exposed to low concentration of bisphenol A. Toxicol Lett 219:116–124

    CAS  Article  Google Scholar 

  34. Rajab M, Greco G, Heim C, Helmreich B, Letzel T (2013a) Serial coupling of RP and zwitterionic hydrophilic interaction LC–MS: suspects screening of diclofenac transformation products by oxidation with a boron-doped diamond electrode. J Sep Sci 36:3011–3018

    CAS  Google Scholar 

  35. Rajab M, Heim C, Greco G, Helmreich B, Letzel T (2013b) Removal of sulfamethoxazole from wastewater treatment plant effluents by a boron-doped diamond electrode. Int J Environ Pollut Solut 1:88–97

    Google Scholar 

  36. Rajab M, Heim C, Letzel T, Drewes JE, Helmreich B (2015) Electrochemical disinfection using boron-doped diamond electrode—the synergetic effects on in situ ozone and free chlorine generation. Chemosphere 121:3011–3018

    Article  Google Scholar 

  37. Rice EW, Baird RB, Eaton AD, Clesceri LS (2012) Standard methods for examination of water and wastewater, 22nd edn. American Public Health Association, Washington, DC

    Google Scholar 

  38. Rivero MJ, Alonso E, Dominguez S, Ribao P, Ibañez R, Ortiz I, Irabien A (2014) Kinetic analysis and biodegradability of the Fenton mineralization of bisphenol A. J Chem Technol Biotechnol 89:1228–1234

    CAS  Article  Google Scholar 

  39. Sarkar S, Ali S, Rehmann L, Nakhla G, Ray MB (2014) Degradation of estrone in water and wastewater by various advanced oxidation processes. J Hazard Mater 278:16–24

    CAS  Article  Google Scholar 

  40. Sharpe RM (2011) Pediatrics: endocrine disruption and human health effects—a call to action. Nat Rev Endocrinol 7:633–634

    Article  Google Scholar 

  41. Sirés I, Brillas E, Oturan MA, Rodrigo MA, Panizza M (2014) Electrochemical advanced oxidation processes: today and tomorrow. A review. Environ Sci Pollut Res Int 21:8336–8367

    Article  Google Scholar 

  42. Ternes TA, Meisenheimer M, McDowell D, Sacher F, Brauch H-J, Haist-Gulde B, Preuss G, Wilme U, Zulei-Seibert N (2002) Removal of pharmaceuticals during drinking water treatment. Environ Sci Technol 36:3855–3863

    CAS  Article  Google Scholar 

  43. Umar M, Roddick F, Fan L, Aziz HA (2013) Application of ozone for the removal of bisphenol A from water and wastewater—a review. Chemosphere 90:2197–2207

    CAS  Article  Google Scholar 

  44. Von Gunten U (2003) Ozonation of drinking water: part I. Oxidation kinetics and product formation. Water Res 37:1443–1467

    Article  Google Scholar 

  45. Warrington P (2002) Ambient water quality guidelines for chlorate. National Library of Canada Cataloguing in Publication Data. http://www.env.gov.bc.ca/wat/wq/BCguidelines/chlorate/chlorate.html. Retrieved 15 Mar 2016

  46. Yates R, Stenstrom MK (2000) Gravimetric sampling procedure for aqueous ozone concentrations. Water Res 34:1413–1416

    CAS  Article  Google Scholar 

  47. Yoshihara S, Murugananthan M (2009) Decomposition of various endocrine-disrupting chemicals at boron-doped diamond electrode. Electrochim Acta 54:2031–2038

    CAS  Article  Google Scholar 

Download references

Acknowledgments

This research was supported by the Federal Ministry of Education and Research of Germany (03X0087G). Students and staff at the Technische Universität München, in particular Markus Orbig and Jürgen Ederer, are gratefully acknowledged for the laboratory work and data analysis. The authors want to thank Sylvia Große for the fruitful discussions.

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Correspondence to B. Helmreich.

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Editorial responsibility: J. Trögl

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Rajab, M., Heim, C., Letzel, T. et al. Oxidation of bisphenol A by a boron-doped diamond electrode in different water matrices: transformation products and inorganic by-products. Int. J. Environ. Sci. Technol. 13, 2539–2548 (2016). https://doi.org/10.1007/s13762-016-1087-z

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Keywords

  • Organic micropollutants
  • Electrochemical advanced oxidation process
  • Degradation products
  • Ozone
  • Wastewater treatment plant effluents