000175329 001__ 175329
000175329 005__ 20181203022641.0
000175329 0247_ $$2doi$$a10.1021/es203348q
000175329 02470 $$2ISI$$a000299136200041
000175329 037__ $$aARTICLE
000175329 245__ $$aKinetic and Mechanistic Investigations of the Oxidation of Tramadol by Ferrate and Ozone
000175329 269__ $$a2012
000175329 260__ $$c2012
000175329 336__ $$aJournal Articles
000175329 520__ $$aThe kinetics and oxidation products (OPs) of tramadol (TRA), an opioid, were investigated for its oxidation with ferrate (Fe(VI)) and ozone (O-3). The kinetics could be explained by the speciation of the tertiary amine moiety of TRA, with apparent second-order rate constants of 7.4 (+/- 04) M-1 s(-1) (Fe(VI)) and 4.2 (+/- 0.3) x 10(4) M-1 s(-1) (O-3) at pH 8.0, respectively. In total, six OPs of TRA were identified for both oxidants using Qq-LIT-MS, LTQFT-MS, GC-MS, and moiety-specific chemical reactions. In excess of oxidants, these OPs can be further transformed to unidentified OPs. Kinetics and OP identification confirmed that the lone electron pair of the amine-N is the predominant site of oxidant attack. An oxygen transfer mechanism can explain the formation of N-oxide-TRA, while a one-electron transfer may result in the formation of N-centered radical cation intermediates, which could lead to the observed N-dealkylation, and to the identified formamide and aldehyde derivatives via several intermediate steps. The proposed radical intermediate mechanism is favored for Fe(VI) leading predominantly to N-desmethyl-TRA (ca. 40%), whereas the proposed oxygen transfer prevails for O-3 attack resulting in N-oxide-TRA as the main OP (ca. 90%).
000175329 6531_ $$aWaste-Water Treatment
000175329 6531_ $$aAqueous-Solution
000175329 6531_ $$aMicropollutant Oxidation
000175329 6531_ $$aNitrilotriacetic Acid
000175329 6531_ $$aInorganic-Compounds
000175329 6531_ $$aPeroxyl Radicals
000175329 6531_ $$aManganese Oxide
000175329 6531_ $$aRate Constants
000175329 6531_ $$aOzonation
000175329 6531_ $$aProducts
000175329 700__ $$0245483$$aZimmermann, Saskia G.$$g212981
000175329 700__ $$aSchmukat, Annekatrin
000175329 700__ $$aSchulz, Manoj
000175329 700__ $$aBenner, Jessica
000175329 700__ $$0245482$$avon Gunten, Urs$$g210253
000175329 700__ $$aTernes, Thomas A.
000175329 773__ $$j46$$q876-884$$tEnvironmental Science & Technology
000175329 909C0 $$0252250$$pLTQE$$xU12400
000175329 909CO $$ooai:infoscience.tind.io:175329$$particle$$pENAC
000175329 917Z8 $$x106743
000175329 937__ $$aEPFL-ARTICLE-175329
000175329 973__ $$aEPFL$$rREVIEWED$$sPUBLISHED
000175329 980__ $$aARTICLE