Advertisement

1,3,5-Tris-(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione: kinetic studies and phototransformation products

  • Dominique Lörchner
  • Lothar W. Kroh
  • Robert KöppenEmail author
Research Article

Abstract

1,3,5-Tris-(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione (TDBP-TAZTO) is an emerging brominated flame retardant which is widely used in several plastic materials (electric and electronic equipment, musical instruments, automotive components). However, until today, no photochemical studies as well as the identification of possible phototransformation products (PTPs) were described in literature. Therefore, in this study, UV-(C) and simulated sunlight irradiation experiments were performed to investigate the photolytic degradation of TDBP-TAZTO and to identify relevant PTPs for the first time. The UV-(C) irradiation experiments show that the photolysis reaction follows a first-order kinetic model. Based on this, the photolysis rate constant k as well as the half-life time t1/2 were calculated to be k = (41 ± 5 × 10−3) min−1 and t1/2 = (17 ± 2) min. In comparison, a minor degradation of TDBP-TAZTO and no formed phototransformation products were obtained under simulated sunlight. In order to clarify the photochemical behavior, different chemicals were added to investigate the influence on indirect photolysis: (i) H2O2 for generation of hydroxyl radicals and (ii) two quenchers (2-propanol, sodium azide) for scavenging oxygen species which were formed during the irradiation experiments. Herein, nine previously unknown PTPs of TDBP-TAZTO were detected under UV-(C) irradiation and identified by HPLC-(HR)MS. As a result, debromination, hydroxylation, and dehydrobromination reactions could be presumed as the main degradation pathways by high-resolution mass spectrometry. The direct as well as the OH radical-induced indirect photolysis were observed.

Graphical abstract

.

Keywords

UV irradiation TDBP-TAZTO Debromination Hydroxylation HRMS Emerging brominated flame retardant 

Notes

Supplementary material

11356_2019_4815_MOESM1_ESM.docx (284 kb)
ESM 1 (DOCX 284 kb)

References

  1. Chen D, Hale RC, Letcher RJ (2015) Photochemical and microbial transformation of emerging flame retardants: cause for concern? Environ Toxicol Chem 34(4):687–699CrossRefGoogle Scholar
  2. Christiansson A, Eriksson J, Teclechiel D, Bergman A (2009) Identification and quantification of products formed via photolysis of decabromodiphenyl ether. Environ Sci Pollut Res Int 16(3):312–321CrossRefGoogle Scholar
  3. Darnerud P (2003) Toxic effects of brominated flame retardants in man and in wildlife. Environ Int 29(6):841–853CrossRefGoogle Scholar
  4. EFSA (2012) Scientific opinion on emerging and novel brominated flame retardants (BFRs) in food. EFSA J 10(10):2908CrossRefGoogle Scholar
  5. Egloff C, Crump D, Chiu S, Manning G, McLaren KK, Cassone CG, Letcher RJ, Gauthier LT, Kennedy SW (2011) In vitro and in ovo effects of four brominated flame retardants on toxicity and hepatic mRNA expression in chicken embryos. Toxicol Lett 207(1):25–33CrossRefGoogle Scholar
  6. Environment Agency, E. a. W, 2010. Environmental prioritisation of low production volume substances under REACH: PBT screening. Environment Agency, Rio House, Waterside Drive, Aztec West, Almondsbury, BristolGoogle Scholar
  7. Hamers T, Kamstra JH, Sonneveld E, Murk AJ, Kester MHA, Andersson PL, Legler J, Brouwer A (2006) In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol Sci :Off J SocToxicol 92(1):157–173CrossRefGoogle Scholar
  8. Kim U-J, Jo H, Lee I-S, Joo G-J, Oh J-E (2015) Investigation of bioaccumulation and biotransformation of polybrominated diphenyl ethers, hydroxylated and methoxylated derivatives in varying trophic level freshwater fishes. Chemosphere 137:108–114CrossRefGoogle Scholar
  9. Law K, Halldorson T, Danell R, Stern G, Gewurtz S, Alaee M, Marvin C, Whittle M, Tomy G (2006) Bioaccumulation and trophic transfer of some brominated flame retardants in a Lake Winnipeg (Canada) food web. Environ Toxicol Chem 25(8):2177–2186CrossRefGoogle Scholar
  10. Leal JF, Esteves VI, Santos EBH (2013) BDE-209: kinetic studies and effect of humic substances on photodegradation in water. Environ Sci Technol 47(24):14010–14017CrossRefGoogle Scholar
  11. Li J, Liang Y, Zhang X, Lu J, Zhang J, Ruan T, Zhou Q, Jiang G (2011) Impaired gas bladder inflation in zebrafish exposed to a novel heterocyclic brominated flame retardant tris(2,3-dibromopropyl) isocyanurate. Environ Sci Technol 45(22):9750–9757CrossRefGoogle Scholar
  12. Li J, Zhang X, Bao J, Liu Y, Li J, Li J, Liang Y, Zhang J, Zhang A (2015) Toxicity of new emerging pollutant tris-(2,3-dibromopropyl) isocyanurate on BALB/c mice. J Appl Toxicol: JAT 35(4):375–382CrossRefGoogle Scholar
  13. Liang D, Wang C, Sun J, Li SP (2016) Photolytic degradation of tris-(2,3-dibromopropyl) isocyanurate (TBC) in aqueous systems. Environ Technol 37(18):2292–2297CrossRefGoogle Scholar
  14. Liu Q, Ren X, Long Y, Hu L, Qu G, Zhou Q, Jiang G (2016) The potential neurotoxicity of emerging tetrabromobisphenol a derivatives based on rat pheochromocytoma cells. Chemosphere 154:194–203CrossRefGoogle Scholar
  15. Pan Y, Tsang DCW, Wang Y, Li Y, Yang X (2016) The photodegradation of polybrominated diphenyl ethers (PBDEs) in various environmental matrices: kinetics and mechanisms. Chem Eng J 297:74–96CrossRefGoogle Scholar
  16. Qu G, Shi J, Li Z, Ruan T, Fu J, Wang P, Wang T, Jiang G (2011) Detection of tris-(2, 3-dibromopropyl) isocyanurate as a neuronal toxicant in environmental samples using neuronal toxicity-directed analysis. Sci China Chem 54(10):1651–1658CrossRefGoogle Scholar
  17. Ruan T, Wang Y, Wang C, Wang P, Fu J, Yin Y, Qu G, Wang T, Jiang G (2009) Identification and evaluation of a novel heterocyclic brominated flame retardant tris(2,3-dibromopropyl) isocyanurate in environmental matrices near a manufacturing plant in Southern China. Environ Sci Technol 43(9):3080–3086CrossRefGoogle Scholar
  18. Stieger G, Scheringer M, Ng CA, Hungerbühler K (2014) Assessing the persistence, bioaccumulation potential and toxicity of brominated flame retardants: data availability and quality for 36 alternative brominated flame retardants. Chemosphere 116:118–123CrossRefGoogle Scholar
  19. Wang L, Zhang M, Lou Y, Ke R, Zheng M (2017) Levels and distribution of tris-(2,3-dibromopropyl) isocyanurate and hexabromocyclododecanes in surface sediments from the Yellow River Delta wetland of China. Mar Pollut Bull 114(1):577–582CrossRefGoogle Scholar
  20. Watanabe I (2003) Environmental release and behavior of brominated flame retardants. Environ Int 29(6):665–682CrossRefGoogle Scholar
  21. Yu Y, Zhou D, Wu F (2015) Mechanism and products of the photolysis of hexabromocyclododecane in acetonitrile–water solutions under a UV-C lamp. Chem Eng J 281:892–899CrossRefGoogle Scholar
  22. Zhang X, Li J, Chen M, Wu L, Zhang C, Zhang J, Zhou Q, Liang Y (2011) Toxicity of the brominated flame retardant tris-(2,3-dibromopropyl) isocyanurate in zebrafish (Danio rerio). Chin Sci Bull 56(15):1548–1555CrossRefGoogle Scholar
  23. Zhang Y-N, Chen J, Xie Q, Li Y, Zhou C (2016) Photochemical transformation of five novel brominated flame retardants: kinetics and photoproducts. Chemosphere 150:453–460CrossRefGoogle Scholar
  24. Zhu N, Li A, Wang T, Wang P, Qu G, Ruan T, Fu J, Yuan B, Zeng L, Wang Y, Jiang G (2012) Tris(2,3-dibromopropyl) isocyanurate, hexabromocyclododecanes, and polybrominated diphenyl ethers in mollusks from Chinese Bohai Sea. Environ Sci Technol 46(13):7174–7181CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Bundesanstalt für Materialforschung und -prüfung (BAM)BerlinGermany
  2. 2.TU Berlin, Institut für Lebensmittelchemie und –technologieBerlinGermany

Personalised recommendations