Chemical Transformation of 3-Bromo-2,2-bis(bromomethyl)propanol under Basic Conditions

Ezra, Shai; Feinstein, Shimon; Bilkis, Itzhak; Adar, Eilon; Ganor, Jiwchar

doi:10.1021/es0495157

Cited by 16 publications

(18 citation statements)

References 26 publications

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“…TBNPA has been reported to be present in ground water in the vicinity of the Negev industrial complex in Israel (Ezra, 2005(Ezra, , 2006. The compound has a relatively strong resistance to biodegradation and therefore classified as not readily biodegradable (0-7 % degradation after 28 days).…”

Section: Sources Use and Environmental Fatementioning

confidence: 99%

“…The mechanism of the spontaneous decomposition of TBNPA) and the kinetics of the reaction of the parent compound and two subsequent degradation products were determined in aqueous solution at temperatures from 30 to 70 °C and pH from 7.0 to 9.5. 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%

“…TBNPA is considered to cause aquatic environmental damage (Ezra, 2005). The mechanism of the spontaneous decomposition of TBNPA) and the kinetics of the reaction of the parent compound and two subsequent degradation products were determined in aqueous solution at temperatures from 30 to 70 °C and pH from 7.0 to 9.5.…”

Section: B R O H B R B Rmentioning

confidence: 99%

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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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Section: Sources Use and Environmental Fatementioning

confidence: 99%

Section: B R O H B R B Rmentioning

confidence: 99%

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

2012

EFS2

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“…Tribromoneopentyl-alcohol (TBNPA) is an intermediate for BFRs, and is used as a reactive flame retardant in polyurethanes (Ezra et al, 2005). It is also present as a semivolatile contaminant in the vadose zone beneath an industrial complex in the northern Negev desert,…”

Section: Photodegradation Of Five Individual Pbdementioning

confidence: 99%

Emerging Chemicals and Analytical Methods

Morley¹,

Snow²,

Fox³

et al. 2004

Water Environment Research

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“…HBCD was transformed in all biotic samples, and half-lives under anaerobic conditions (ranging from 1.1-6.9 d) were much shorter than those for aerobic conditions (11-63 d) for similar soil or sediment. Although some loss of HBCD was observed in abiotic controls, biotransformation clearly was an important removal mechanism in biotic microcosms.Tribromoneopentyl-alcohol (TBNPA) is an intermediate for BFRs, and is used as a reactive flame retardant in polyurethanes(Ezra et al, 2005). It is also present as a semivolatile contaminant in the vadose zonebeneath an industrial complex in the northern Negev desert, Israel.…”

mentioning

confidence: 99%