Photodegradation of the novel brominated flame retardant 2,4,6-Tris-(2,4,6-tribromophenoxy)-1,3,5-triazine in solvent system: Kinetics, photolysis products and pathway. 2019

Dominique Lörchner, and Werner Kraus, and Robert Köppen
Bundesanstalt für Materialforschung und -prüfung (BAM), Richard-Willstätter-Str. 11, D-12489, Berlin, Germany; TU Berlin, Institut für Lebensmitteltechnologie und Lebensmittelchemie, Gustav-Meyer-Allee 25, D-13305, Berlin, Germany.

In this study the direct and indirect photolysis of the novel brominated flame retardant 2,4,6-Tris-(2,4,6-tribromophenoxy)-1,3,5-triazine (TTBP-TAZ) in an organic solvent mixture (60:30:10, ACN:MeOH:THF) under UV-(C) and simulated sunlight irradiation was investigated, and the formed photo-transformation products were identified for the first time. TTBP-TAZ was almost completely degraded within 10 min under UV-(C) irradiation. Due to the fast degradation no specific kinetic order could be observed. In comparison, the reaction under simulated sunlight irradiation was much slower and thus, the kinetic first-order could be determined. The observed photolysis rate constant k as well as the half-life time t1/2 were estimated to be k = (0.0163 ± 0.0002) h-1 and t1/2 = 42.3 h, respectively. The addition of 2-propanol and hydrogen peroxide to investigate the influence of indirect photolysis under UV-(C) irradiation causes no influence on the degradation of TTBP-TAZ. Nevertheless, the removal of TTBP-TAZ under UV-(C) and simulated sunlight without additional chemicals (except solvent) indicates that the direct photolysis plays a significant role in the degradation mechanism of TTBP-TAZ. In both irradiation experiments, TTBP-TAZ was quantitatively degraded that involve the formation of previously unknown PTPs. Overall, two main PTPs were determined when irradiated with UV-(C) and eight sequential debromination products were observed when irradiated by simulated sunlight. These were determined by HPLC-DAD and - MS/(MS), respectively. Based on the chosen experimental conditions the consecutive debromination as well as photo-Fries rearrangement was confirmed as the main degradation pathway by high resolution mass spectrometry and X-ray diffraction.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D010782 Photolysis Chemical bond cleavage reactions resulting from absorption of radiant energy. Photodegradation
D005411 Flame Retardants Materials applied to fabrics, bedding, furniture, plastics, etc. to retard their burning; many may leach out and cause allergies or other harm. Fire Retardant,Fire Retardants,Fireproofing Agent,Fireproofing Agents,Flame Retardant,Agent, Fireproofing,Agents, Fireproofing,Retardant, Fire,Retardant, Flame,Retardants, Fire,Retardants, Flame
D006842 Hydrocarbons, Brominated Hydrocarbon compounds with one or more HYDROGEN atoms substituted with BROMINE. Brominated Hydrocarbons
D014227 Triazines Heterocyclic rings containing three nitrogen atoms, commonly in 1,2,4 or 1,3,5 or 2,4,6 formats. Some are used as HERBICIDES. Triazine,Benzotriazines
D054879 Halogenation Covalent attachment of HALOGENS to other compounds. Bromination,Chlorination,Fluorination,Iodination,Iodation

Related Publications

Dominique Lörchner, and Werner Kraus, and Robert Köppen
March 2018, Environmental science & technology,
Dominique Lörchner, and Werner Kraus, and Robert Köppen
December 2014, Environmental science & technology,
Dominique Lörchner, and Werner Kraus, and Robert Köppen
March 2024, Environmental pollution (Barking, Essex : 1987),
Dominique Lörchner, and Werner Kraus, and Robert Köppen
June 2019, Environmental science and pollution research international,
Dominique Lörchner, and Werner Kraus, and Robert Köppen
April 2014, Environmental science & technology,
Dominique Lörchner, and Werner Kraus, and Robert Köppen
September 2022, International journal of environmental research and public health,
Copied contents to your clipboard!