Aerobic biodegradation of the brominated flame retardants, dibromoneopentyl glycol and tribromoneopentyl alcohol

Segev, Osnat; Meusel, Wolfram; Friedenberger, Melanie; Brenner, Asher; Kushmaro, Ariel

doi:10.1007/s10532-009-9249-z

Cited by 15 publications

(15 citation statements)

References 29 publications

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“…The peak identified as HBCD elutes in the region where the hexa-BDEs elute, similar to the elution order previously reported by Korytár et al (2002) [10]. Tribromoneopentyl alcohol is a reactive BFR used in the synthesis of high molecular-weight flame retardants and as an additive in the manufacturing of polymers [41].…”

Section: Identification Of Ohcssupporting

confidence: 86%

Comprehensive two-dimensional gas chromatography coupled to high resolution time-of-flight mass spectrometry for screening of organohalogenated compounds in cat hair

Brits

Gorst-Allman²,

Rohwer

et al. 2018

Journal of Chromatography A

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The coupling of comprehensive two-dimensional gas chromatography with high-resolution time-of-flight mass spectrometry offers the best separation efficiency combined with accurate mass measurements over a wide mass range. The tremendous power of this screening tool is illustrated by trace qualitative screening analysis of organohalogenated compounds (OHCs) in pet cat hair. Tentative identification was supported by mass spectral database searches and elemental formula prediction from the experimentally determined accurate mass data. This screening approach resulted in the first tentative identification of pentabromoethylbenzene, decabromodiphenyl ethane, hexabromocyclododecane, trisbromoneopentyl alcohol, tris(2-chloroethyl) phosphate and tris(2-chloroisopropyl)phosphate in the South African indoor environment. A total of seventy-two OHCs were identified in the samples and include known flame retardants, such as polybrominated diphenyl ethers, and legacy contaminants such as polychlorinated biphenyls and organochlorine, organophosphorous and pyrethroid pesticides. The results obtained from cat hair indicate that these pets are exposed to complex mixtures of OHCs and the detection of these compounds suggests that non-invasive cat hair samples can be used to model indoor exposure with reference to external deposition of OHCs present in the air and dust surrounding people. Toddlers share the same environment as pet cats and therefore also the same health risks.

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Section: Identification Of Ohcssupporting

confidence: 86%

Comprehensive two-dimensional gas chromatography coupled to high resolution time-of-flight mass spectrometry for screening of organohalogenated compounds in cat hair

Brits

Gorst-Allman²,

Rohwer

et al. 2018

Journal of Chromatography A

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“…It was found that TBNPA could be decomposed by a sequence of reactions that form 3,3-bis(bromomethyl)oxetane, 3-bromomethyl-3-hydroxymethyloxetane, and 2,6-dioxaspiro[3.3]-heptane (DOH), releasing one bromide ion at each stage (Ezra et al, 2005). Segev et al (2009) have experimentally confirmed that TBNPA can undergo microbiological degradation and that the process can be facilitated in order to improve treatment of ground water.…”

Section: B R O H B R B Rmentioning

confidence: 99%

Scientific Opinion on Emerging and Novel Brominated Flame Retardants (BFRs) in Food

2012

EFS2

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EFSA was asked to deliver a scientific opinion on brominated flame retardants (BFRs) other than PBDEs, PBBs, HBCDDs, TBBPA and brominated phenols and their derivatives. The BFRs that are the subject of the current opinion, were classified in groups termed "emerging" and "novel" BFRs. Information on 17 emerging and 10 novel BFRs was collected. The information varied widely for these BFRs. There is a lack of experimental data on physico-chemical characteristics, stability/reactivity and current use and production volume of all the emerging and novel BFRs. Due to the very limited information on occurrence, exposure and toxicity, the CONTAM Panel could not perform a risk characterisation for any of the BFRs considered. Instead, an attempt was made to identify those BFRs that could be a potential health concern and should be considered first for future investigations. For this purpose the Panel first evaluated the available experimental data on occurrence in food, behaviour in the environment and toxicity. Secondly, a modelling exercise was performed focussing on the potential of the emerging and novel BFRs for persistence in the environment and for their possible bioaccumulation potential. There is convincing evidence that tris(2,3-dibromopropyl) phosphate (TDBPP) and dibromoneopentyl glycol (DBNPG) are genotoxic and carcinogenic, warranting further surveillance of their occurrence in the environment and in food. Based on the limited experimental data on environmental behaviour, 1,2-bis(2,4,6-tribromophenoxy)ethane (BTBPE) and hexabromobenzene (HBB) were identified as compounds that could raise a concern for bioaccumulation. For the modelling exercise, the CONTAM Panel selected two environmental characteristics, overall persistence and potential for bioaccumulation, as being most relevant to provide insight into the possibility that emerging or novel BFRs The less well known and less studied BFRs, subject of the current opinion, were grouped into two classes, referred to herein as "emerging" and "novel" BFRs. Emerging BFRs are defined as chemicals which are applied as flame retardants and that have been identified in any environmental compartment, in wildlife, in food or in humans. It should be noted that the definition for the emerging BFRs, used in this opinion, does not imply that there is evidence for an increasing trend in the concentration of these BFRs in the environment, in food or in human samples. Novel BFRs are defined as chemicals applied as flame retardants, with confirmed presence in materials and/or goods in concentrations above 0.1 %, but not identified in environmental samples, wildlife, food or humans. In total, information on 27 BFRs, of which 17 were identified as "emerging" and 10 as "novel", was collected by the CONTAM Panel, and it was noted that the available information varied widely for the various individual BFRs.In general, there is a lack of experimental data on physico-chemical characteristics and stability/reactivity for all the emerging and novel BFRs. This sometimes hampered ...

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“…It is heavily used as a flame retardant in urethane foam, but little to no information was previously available concerning its potential to induce toxicity [ 38 ]. DBNPG did not induce mortality or malformations in this model, and very little research has been conducted on this chemical, with most focusing on the biodegradation [ 39 ].…”

Section: Discussionmentioning

confidence: 99%

Evaluation of Common Use Brominated Flame Retardant (BFR) Toxicity Using a Zebrafish Embryo Model

Usenko

Abel

Hopkins

et al. 2016

Toxics

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Brominated flame retardants (BFRs) are used to reduce the flammability of plastics, textiles, and electronics. BFRs vary in their chemical properties and structures, and it is expected that these differences alter their biological interactions and toxicity. Zebrafish were used as the model organism for assessing the toxicity of nine structurally-diverse BFRs. In addition to monitoring for overt toxicity, the rate of spontaneous movement, and acetylcholinesterase and glutathione-S-transferase (GST) activities were assessed following exposure. The toxicities of BFRs tested can be ranked by LC50 as tetrabromobisphenol A (TBBPA) < 4,4′-isopropylidenebis[2-(2,6-dibromophenoxyl)ethanol] (TBBPA-OHEE) < Pentabromochlorocyclohexane (PBCH) < 2-ethylhexyl 2,3,4,5-tetrabromobenzoate (TBB) < hexabromocyclododecane (HBCD) < hexabromobenzene (HBB) < Tetrabromophthalic anhydride (PHT4). No adverse effect was observed in di(2-ethylhexyl) tetrabromophthalate (TBPH) or dibromoneopentyl glycol (DBNPG)-treated embryos. The rate of spontaneous movement was decreased in a concentration-dependent manner following exposure to four of the nine compounds. GST activity was elevated following treatment with PBCH, TBBPA, HBCD, and HBB. The results indicate that exposure to several BFRs may activate an antioxidant response and alter behavior during early development. Some of the BFRs, such as TBBPA and TBBPA-OHEE, induced adverse effects at concentrations lower than chemicals that are currently banned. These results suggest that zebrafish are sensitive to exposure to BFRs and can be used as a comparative screening model, as well as to determine alterations in behavior following exposure and probe mechanisms of action.

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Aerobic biodegradation of the brominated flame retardants, dibromoneopentyl glycol and tribromoneopentyl alcohol

Cited by 15 publications

References 29 publications

Comprehensive two-dimensional gas chromatography coupled to high resolution time-of-flight mass spectrometry for screening of organohalogenated compounds in cat hair

Comprehensive two-dimensional gas chromatography coupled to high resolution time-of-flight mass spectrometry for screening of organohalogenated compounds in cat hair

Scientific Opinion on Emerging and Novel Brominated Flame Retardants (BFRs) in Food

Evaluation of Common Use Brominated Flame Retardant (BFR) Toxicity Using a Zebrafish Embryo Model

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