Catalytic oxidative degradation of 17α-ethinylestradiol by FeIII-TAML/H2O2: Estrogenicities of the products of partial, and extensive oxidation

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dc.contributor.author Chen, JL en
dc.contributor.author Ravindran, S en
dc.contributor.author Swift, Simon en
dc.contributor.author Wright, Leonard en
dc.contributor.author Singhal, Naresh en
dc.date.accessioned 2015-04-24T00:49:31Z en
dc.date.available 2012-09-03 en
dc.date.issued 2012-12-01 en
dc.identifier.citation Water Research, 2012, 46 (19), pp. 6309 - 6318 (10) en
dc.identifier.issn 0043-1354 en
dc.identifier.uri http://hdl.handle.net/2292/25292 en
dc.description.abstract The oxidative degradation of the oral contraceptive 17α-ethinylestradiol (EE2) in water by a new advanced catalytic oxidation process was investigated. The oxidant employed was hydrogen peroxide in aqueous solution and the catalyst was the iron tetra-amido macrocyclic ligand (FeIII-TAML) complex that has been designated Na[Fe(H2O)(B*)] (FeIII-B*). EE2 (10 μM) was oxidised rapidly by the FeIII-B*/H2O2 (5 nM/4 mM) catalytic oxidation system at 25 °C, and for reactions at pH 8.40–11.00, no unchanged EE2 was detected in the reaction mixtures after 60 min. No oxidation of EE2 was detected in blank reactions using either H2O2 or FeIII-B* alone. The maximum rate of EE2 loss occurred at pH 10.21. At this pH the half-life of EE2 was 2.1 min and the oxidised products showed around 30% estrogenicity removal, as determined by the yeast estrogen screen (YES) bioassay. At pH 11.00, partial oxidation of EE2 by FeIII-B*/H2O2 (5 nM/4 mM) was studied (half-life of EE2 was 14.5 min) and in this case the initial intermediates formed were a mixture of the epimers 17α-ethynyl-1,4-estradiene-10α,17β-diol-3-one (1a) and 17α-ethynyl-1,4-estradiene-10β,17β-diol-3-one (1b) (identified by LC-ToF-MS and 1H NMR spectroscopy). Significantly, this product mixture displayed a slightly higher estrogenicity than EE2 itself, as determined by the YES bioassay. Upon the addition of further aliquots of FeIII-B* (to give a FeIII-B* concentration of 500 nM) and H2O2 (to bring the concentration up to 4 mM assuming the final concentration had dropped to zero) to this reaction mixture the amounts of 1a and 1b slowly decreased to zero over a 60 min period as they were oxidised to unidentified products that showed no estrogenicity. Thus, partial oxidation of EE2 gave products that have slightly increased estrogenicity, whereas more extensive oxidation by the advanced catalytic oxidation system completely removed all estrogenicity. These results underscore the importance of controlling the level of oxidation during the removal of EE2 from water by oxidative processes en
dc.language eng en
dc.publisher Elsevier en
dc.relation.ispartofseries Water Research en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0043-1354/ http://www.elsevier.com/journals/water-research/0043-1354/guide-for-authors#10010 en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Catalytic oxidative degradation of 17α-ethinylestradiol by FeIII-TAML/H2O2: Estrogenicities of the products of partial, and extensive oxidation en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.watres.2012.09.012 en
pubs.issue 19 en
pubs.begin-page 6309 en
pubs.volume 46 en
dc.rights.holder Copyright: Elsevier en
dc.identifier.pmid 23022118 en
pubs.author-url http://www.sciencedirect.com/science/article/pii/S0043135412006550 en
pubs.end-page 6318 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 361652 en
pubs.org-id Engineering en
pubs.org-id Civil and Environmental Eng en
pubs.org-id Medical and Health Sciences en
pubs.org-id Medical Sciences en
pubs.org-id Molecular Medicine en
pubs.org-id Science en
pubs.org-id Chemistry en
dc.identifier.eissn 1879-2448 en
pubs.record-created-at-source-date 2012-12-04 en
pubs.dimensions-id 23022118 en


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