Simulation of the Environmental Degradation of TBBPA by EC-LC-MS
- Oxidative degradation processes of tetrabromobisphenol A (TBBPA), a brominated flame retardant (BFR) in wood, plastics and electronics, were investigated by electrochemistry (EC) coupled online to electrospray ionization mass spectrometry (ESI/MS). Oxidative phase I and II metabolites production was achieved using an electrochemical flow-through cell equipped with a boron doped diamond electrode. Structural elucidation and prediction of oxidative metabolism pathways of TBBPA according to type II ipso-substitution were based on retention time, m/z ratio in negative mode and fragmentation pattern. Using the data obtained through high resolution MS analysis and the identification of single electron transfer (SET) as the initial step of a two-electron oxidation provided the necessary information to propose a mechanism for the electrochemical oxidation of TBBPA. Oxidation reactions involving aromatic hydroxylation and β-scission were the main degradation observed when studying theOxidative degradation processes of tetrabromobisphenol A (TBBPA), a brominated flame retardant (BFR) in wood, plastics and electronics, were investigated by electrochemistry (EC) coupled online to electrospray ionization mass spectrometry (ESI/MS). Oxidative phase I and II metabolites production was achieved using an electrochemical flow-through cell equipped with a boron doped diamond electrode. Structural elucidation and prediction of oxidative metabolism pathways of TBBPA according to type II ipso-substitution were based on retention time, m/z ratio in negative mode and fragmentation pattern. Using the data obtained through high resolution MS analysis and the identification of single electron transfer (SET) as the initial step of a two-electron oxidation provided the necessary information to propose a mechanism for the electrochemical oxidation of TBBPA. Oxidation reactions involving aromatic hydroxylation and β-scission were the main degradation observed when studying the electrochemical behavior of TBBPA. Computational chemistry experiments using density functional theory (DFT) allowed to identify mono-hydroxylated reaction intermediate and dismissed the mechanism involving two concurrent hydroxylation. TBBPA oxidation products were compared to known metabolites of its biological and environmental degradation confirming the ability of electrochemistry to simulate β-scission reactions.…
Autor*innen: | Ranil C. Temgoua Tonleu, Matthias KochORCiD |
---|---|
Dokumenttyp: | Posterpräsentation |
Veröffentlichungsform: | Präsentation |
Sprache: | Englisch |
Jahr der Erstveröffentlichung: | 2024 |
Organisationseinheit der BAM: | 1 Analytische Chemie; Referenzmaterialien |
1 Analytische Chemie; Referenzmaterialien / 1.7 Organische Spuren- und Lebensmittelanalytik | |
DDC-Klassifikation: | Naturwissenschaften und Mathematik / Chemie / Analytische Chemie |
Freie Schlagwörter: | Chemical and material safety; Chemical characterization; Electrochemistry; Emerging pollutants; Environment-material interactions; Mass spectrometry |
Themenfelder/Aktivitätsfelder der BAM: | Chemie und Prozesstechnik |
Chemie und Prozesstechnik / Chemische Charakterisierung und Spurenanalytik | |
Veranstaltung: | Mass Spectrometry Forum 2024 |
Veranstaltungsort: | Vienna, Austria |
Beginndatum der Veranstaltung: | 21.02.2024 |
Enddatum der Veranstaltung: | 23.02.2024 |
Verfügbarkeit des Dokuments: | Datei im Netzwerk der BAM verfügbar ("Closed Access") |
Datum der Freischaltung: | 27.02.2024 |
Referierte Publikation: | Nein |