Degradation of progestagens by oxidation with potassium permanganate in wastewater effluents

Chemistry Central Journal

Volumn 7, Issue 1, 2013, Pages

  Fayad, Paul B ^a   Zamyadi, Arash ^b   Broseus, Romain ^b   Prévost, Michèle ^b   Sauvé, Sébastien ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

^b ÉCOLE POLYTECHNIQUE DE MONTRÉAL   (Canada)

Author keywords

Endocrine disruptors; Kinetic rate constant; LDTD APCI MSMS; Oxidation; Potassium permanganate; Steroid hormones

Indexed keywords

EID: 84878643016     PISSN: None     EISSN: 1752153X     Source Type: Journal    
DOI: 10.1186/1752-153X-7-84     Document Type: Article

References (62)

1. Ternes TA, Joss A. Human Pharmaceuticals, Hormones and Fragrances. The Challenge of Micropollutants in Urban Water Management 2007, London: IWA Publishing.
2. Kolpin DW, Furlong ET, Meyer MT, Thurman EM, Zaugg SD, Barber LB, Buxton HT. Pharmaceuticals, Hormones, and Other Organic Wastewater Contaminants in U.S. Streams, 1999-2000: A National Reconnaissance. Environ Sci Technol 2002, 36:1202-1211. 10.1021/es011055j, 11944670.
3. Servos MR, Bennie DT, Burnison BK, Jurkovic A, McInnis R, Neheli T, Schnell A, Seto P, Smyth SA, Ternes TA. Distribution of estrogens, 17[beta]-estradiol and estrone, in Canadian municipal wastewater treatment plants. Sci Total Environ 2005, 336:155-170. 10.1016/j.scitotenv.2004.05.025, 15589256.
4. Ying GG, Kookana RS, Ru YJ. Occurrence and fate of hormone steroids in the environment. Environ Int 2002, 28:545-551. 10.1016/S0160-4120(02)00075-2, 12503920.
5. Purdom CE, Hardiman PA, Bye VVJ, Eno NC, Tyler CR, Sumpter JP. Estrogenic Effects of Effluents from Sewage Treatment Works. Chem Ecol 1994, 8:275-285.
6. Routledge EJ, Sheahan D, Desbrow C, Brighty GC, Waldock M, Sumpter JP. Identification of Estrogenic Chemicals in STW Effluent. 2. In Vivo Responses in Trout and Roach. Environ Sci Technol 1998, 32:1559-1565.
7. Desbrow C, Routledge EJ, Brighty GC, Sumpter JP, Waldock M. Identification of Estrogenic Chemicals in STW Effluent. 1. Chemical Fractionation and in Vitro Biological Screening. Environ Sci Technol 1998, 32:1549-1558.
8. Lopez de Alda MJ, Diaz-Cruz S, Petrovic M, Barcelo D. Liquid chromatography-(tandem) mass spectrometry of selected emerging pollutants (steroid sex hormones, drugs and alkylphenolic surfactants) in the aquatic environment. J Chrom A 2003, 1000:503-526.
9. Auriol M, Filali-Meknassi Y, Tyagi RD, Adams CD, Surampalli RY. Endocrine disrupting compounds removal from wastewater, a new challenge. Process Biochem 2006, 41:525-539.
10. Lopez de Alda MJ, Barcelo D. Review of analytical methods for the determination of estrogens and progestogens in waste waters. Fresenius J Anal Chem 2001, 371:437-447. 10.1007/s002160101027, 11760051.
11. Briciu RD, Kot-Wasik A, Namiesnik J. Analytical Challenges and Recent Advances in the Determination of Estrogens in Water Environments. J Chrom Sci 2009, 47:127-139.
12. Viglino L, Aboulfadl K, Prevost M, Sauve S. Analysis of natural and synthetic estrogenic endocrine disruptors in environmental waters using online preconcentration coupled with LC-APPI-MS/MS. Talanta 2008, 76:1088-1096. 10.1016/j.talanta.2008.05.008, 18761160.
13. Tomsikova H, Aufartova J, Solich P, Novakova L, Sosa-Ferrera Z, Santana-Rodriguez JJ. High-sensitivity analysis of female-steroid hormones in environmental samples. TrAC Trends Anal Chem 2012, 34:35-58.
14. Chang H, Wan Y, Wu S, Fan Z, Hu J. Occurrence of androgens and progestogens in wastewater treatment plants and receiving river waters: Comparison to estrogens. Water Res 2011, 45:732-740. 10.1016/j.watres.2010.08.046, 20850861.
15. Sumpter JP, Johnson AC. Lessons from Endocrine Disruption and Their Application to Other Issues Concerning Trace Organics in the Aquatic Environment. Environ Sci Technol 2005, 39:4321-4332. 10.1021/es048504a, 16047764.
16. Liu Z, Ogejo JA, Pruden A, Knowlton KF. Occurrence, fate and removal of synthetic oral contraceptives (SOCs) in the natural environment: A review. Sci Total Environ 2011, 409:5149-5161. 10.1016/j.scitotenv.2011.08.047, 21975000.
17. Besse JP, Garric J. Progestagens for human use, exposure and hazard assessment for the aquatic environment. Environ Pollut 2009, 157:3485-3494. 10.1016/j.envpol.2009.06.012, 19615798.
18. Kobayashi M, Sorensen P, Stacey N. Hormonal and pheromonal control of spawning behavior in the goldfish. Fish Physiol Biochem 2002, 26:71-84.
19. Kolodziej EP, Gray JL, Sedlak DL. Quantification of steroid hormones with pheromonal properties in municipal wastewater effluent. Environ Toxicol Chem 2003, 22:2622-2629. 10.1897/03-42, 14587901.
20. Dinger JC, Heinemann LAJ, Kuhl-Habich D. The safety of a drospirenone-containing oral contraceptive: final results from the European Active Surveillance study on Oral Contraceptives based on 142,475 women-years of observation. Contraception 2007, 75:344-354. 10.1016/j.contraception.2006.12.019, 17434015.
21. Runnalls TJ, Margiotta-Casaluci L, Kugathas S, Sumpter JP. Pharmaceuticals in the Aquatic Environment: Steroids and Anti-Steroids as High Priorities for Research. Hum Ecol Risk Assess 2010, 16:1318-1338.
22. Shore LS, Shemesh M. Naturally produced steroid hormones and their release into the environment. Pure Appl Chem 2003, 75:1859-1871.
23. Koubovec D, Ronacher K, Stubsrud E, Louw A, Hapgood JP. Synthetic progestins used in HRT have different glucocorticoid agonist properties. Mol Cell Endocrinol 2005, 242:23-32. 10.1016/j.mce.2005.07.001, 16125839.
24. Shao X, Ma J, Wen G, Yang J. Oxidationof estrone by permanganate: reaction kinetics and estrogenicity removal. Chin Sci Bull 2010, 55:802-808.
25. Guan X, He D, Ma J, Chen G. Application of permanganate in the oxidation of micropollutants: a mini review. Front Environ Sci Engin China 2010, 4:405-413.
26. Jiang J, Pang SY, Ma J, Liu H. Oxidation of Phenolic Endocrine Disrupting Chemicals by Potassium Permanganate in Synthetic and Real Waters. Environ Sci Technol 2012, 46:1774-1781. 10.1021/es2035587, 22208220.
27. Hu L, Martin HM, Arce-Bulted O, Sugihara MN, Keating KA, Strathmann TJ. Oxidation of Carbamazepine by Mn(VII) and Fe(VI): Reaction Kinetics and Mechanism. Environ Sci Technol 2008, 43:509-515.
28. Hu L, Martin HM, Strathmann TJ. Oxidation kinetics of antibiotics during water treatment with potassium permanganate. Environ Sci Technol 2010, 44:6416-6422. 10.1021/es101331j, 20704243.
29. Dash S, Patel S, Mishra BK. Oxidation by permanganate: synthetic and mechanistic aspects. Tetrahedron 2009, 65:707-739.
30. Rodriguez E, Majado ME, Meriluoto J, Acero JL. Oxidation of microcystins by permanganate: reaction kinetics and implications for water treatment. Water Res 2007, 41:102-110. 10.1016/j.watres.2006.10.004, 17097716.
31. Ma J, Graham N. Controlling the formation of chloroform by permanganate preoxidation-Destruction of precursors. J Water Supply Res Technol -AQUA 1996, 45:308-315.
32. Korshin GV, Chang HS, Frenkel AI, Ferguson JF. Structural Study of the Incorporation of Heavy Metals into Solid Phase Formed during the Oxidation of EDTA by Permanganate at High pH. Environ Sci Technol 2007, 41:2560-2565. 10.1021/es062554t, 17438816.
33. Waldemer RH, Tratnyek PG. Kinetics of contaminant degradation by permanganate. Environ Sci Technol 2006, 40:1055-1061. 10.1021/es051330s, 16509357.
34. Sharp EL, Parsons SA, Jefferson B. Seasonal variations in natural organic matter and its impact on coagulation in water treatment. Sci Total Environ 2006, 363:183-194. 10.1016/j.scitotenv.2005.05.032, 15987654.
35. Sharp EL, Jarvis P, Parsons SA, Jefferson B. Impact of fractional character on the coagulation of NOM. Colloids Surf A Physicochem Eng Asp 2006, 286:104-111.
36. Fabris R, Chow CWK, Drikas M, Eikebrokk B. Comparison of NOM character in selected Australian and Norwegian drinking waters. Water Res 2008, 42:4188-4196. 10.1016/j.watres.2008.06.023, 18706670.
37. Forsberg C. Will an increased greenhouse impact in Fennoscandia give rise to more humic and coloured lakes?. Hydrobiologia 1992, 229:51-58.
38. Eikebrokk B, Vogt RD, Liltved H. NOM increase in Northern European source waters: Discussion of possible causes and impacts on coagulation/contact filtration processes. Water Sci Technol Water Supply 2004, 4:45-54.
39. Worrall F, Burt TP. Trends in DOC concentration in Great Britain. J Hydrol 2007, 346:81-92.
40. Worrall F, Burt TP. Changes in DOC treatability: Indications of compositional changes in DOC trends. J Hydrol 2009, 366:1-8.
41. Matilainen A, Sillanpää M. Removal of natural organic matter from drinking water by advanced oxidation processes. Chemosphere 2010, 80:351-365. 10.1016/j.chemosphere.2010.04.067, 20494399.
42. Pereira RO, Postigo C, de Alda ML, Daniel LA, Barcelo D. Removal of estrogens through water disinfection processes and formation of by-products. Chemosphere 2011, 82:789-799. 10.1016/j.chemosphere.2010.10.082, 21087787.
43. Broseus R, Vincent S, Aboulfadl K, Daneshvar A, Sauve S, Barbeau B, Prevost M. Ozone oxidation of pharmaceuticals, endocrine disruptors and pesticides during drinking water treatment. Water Res 2009, 43:4707-4717. 10.1016/j.watres.2009.07.031, 19695660.
44. Fayad PB, Prevost M, Sauve S. Laser Diode Thermal Desorption/Atmospheric Pressure Chemical Ionization Tandem Mass Spectrometry Analysis of Selected Steroid Hormones in Wastewater: Method Optimization and Application. Anal Chem 2010, 82:639-645. 10.1021/ac902074x, 20000768.
45. AFNOR Recueil de Normes Françaises; Qualité de l'Eau (French standards and regulations for the quality of water) 1994, 403. Paris: Association Française de Normalisation, AFNOR.
46. Jiang J, Pang SY, Ma J. Role of Ligands in Permanganate Oxidation of Organics. Environ Sci Technol 2010, 44:4270-4275. 10.1021/es100038d, 20429549.
47. Jiang J, Pang SY, Ma J. Oxidation of Triclosan by Permanganate (Mn(VII)): Importance of Ligands and In Situ Formed Manganese Oxides. Environ Sci Technol 2009, 43:8326-8331. 10.1021/es901663d, 19924964.
48. Yan YE, Schwartz FW. Kinetics and Mechanisms for TCE Oxidation by Permanganate. Environ Sci Technol 2000, 34:2535-2541.
49. Deborde M, Rabouan S, Gallard H, Legube B. Aqueous chlorination kinetics of some endocrine disruptors. Environ Sci Technol 2004, 38:5577-5583. 10.1021/es040006e, 15575274.
50. Barbeau B, Desjardins R, Mysore C, Prevost M. Impacts of water quality on chlorine and chlorine dioxide efficacy in natural waters. Water Res 2005, 39:2024-2033. 10.1016/j.watres.2005.03.025, 15922397.
51. Schulten HR. Models of Humic Structures: Association of Humic Acids and Organic Matter in Soils and Water. Humic Substances and Chemical Contaminants 2001, 73-87. Madison, WI: Soil Science Society of America, Clapp CE, Hayes MHB, Senesi N, Bloom PR, Jardine PM.
52. He D, Guan X, Ma J, Yang X, Cui C. Influence of humic acids of different origins on oxidation of phenol and chlorophenols by permanganate. J Hazard Mater 2010, 182:681-688. 10.1016/j.jhazmat.2010.06.086, 20633987.
53. Karanfil T, Kilduff JE, Schlautman MA, Weber WJ. Adsorption of Organic Macromolecules by Granular Activated Carbon. 1. Influence of Molecular Properties Under Anoxic Solution Conditions. Environ Sci Technol 1996, 30:2187-2194.
54. Karanfil T, Schlautman MA, Kilduff JE, Weber WJ. Adsorption of Organic Macromolecules by Granular Activated Carbon. 2. Influence of Dissolved Oxygen. Environ Sci Technol 1996, 30:2195-2201.
55. Chiou CT, Kile DE, Brinton TI, Malcolm RL, Leenheer JA, MacCarthy P. A comparison of water solubility enhancements of organic solutes by aquatic humic materials and commercial humic acids. Environ Sci Technol 1987, 21:1231-1234.
56. Chin YP, Weber WJ. Estimating the effects of dispersed organic polymers on the sorption of contaminants by natural solids. I. A predictive thermodynamic humic substance organic solute interaction model. Environ Sci Technol 1989, 23:978-984.
57. Ghosh K, Schnitzer M. Macromolecular structures of humic substances. Soil Sci 1980, 126:266-276.
58. Schlautman MA, Morgan JJ. Effects of aqueous chemistry on the binding of polycyclic aromatic hydrocarbons by dissolved humic materials. Environ Sci Technol 1993, 27:961-969.
59. Cameron RS, Thornton BK, Swift RS, Posner AM. Molecular weight and shape of humic acid from sedimentation and diffusion measurements on fractionated extracts. J Soil Sci 1972, 23:394-408.
60. Chen X, Xiao B, Liu J, Fang T, Xu X. Kinetics of the oxidation of MCRR by potassium permanganate. Toxicon 2005, 45:911-917. 10.1016/j.toxicon.2005.02.011, 15904686.
61. Huang KC, Hoag GE, Chheda P, Woody BA, Dobbs GM. Kinetics and mechanism of oxidation of tetrachloroethylene with permanganate. Chemosphere 2002, 46:815-825. 10.1016/S0045-6535(01)00186-2, 11922062.
62. Huang KC, Hoag GE, Chheda P, Woody BA, Dobbs GM. Oxidation of chlorinated ethenes by potassium permanganate: a kinetics study. J Hazard Mater 2001, 87:155-169. 10.1016/S0304-3894(01)00241-2, 11566407.