Tetrabromobisphenol A

Last updated
Tetrabromobisphenol A
Tetrabromobisphenol A.svg
Names
Preferred IUPAC name
4,4′-(Propane-2,2-diyl)bis(2,6-dibromophenol)
Other names
2,2′,6,6′-Tetrabromobisphenol A, 2,2′,6,6′-Tetrabromo-4,4′-isopropylidenediphenol, 2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane, 4,4′-Isopropylidenebis(2,6-dibromophenol)
Identifiers
3D model (JSmol)
AbbreviationsTBBPA, TBBP-A, TBBA
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.125 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-236-9
KEGG
MeSH C443737
PubChem CID
UNII
  • InChI=1S/C15H12Br4O2/c1-15(2,7-3-9(16)13(20)10(17)4-7)8-5-11(18)14(21)12(19)6-8/h3-6,20-21H,1-2H3 X mark.svgN
    Key: VEORPZCZECFIRK-UHFFFAOYSA-N X mark.svgN
  • CC(C)(c1cc(Br)c(O)c(Br)c1)c1cc(Br)c(O)c(Br)c1
Properties
C15H12Br4O2
Molar mass 543.9 g·mol −1
Density 2,12 g·cm−3 (20 °C) [1]
Melting point 178 °C (352 °F; 451 K) [1]
Boiling point 250 °C (482 °F; 523 K) (decomposition) [1]
insoluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
N [1]
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant. The compound is a white solid (not colorless), although commercial samples appear yellow. It is one of the most common flame retardants. [2]

Contents

Production and use

TBBPA is produced by the reaction of bromine with bisphenol A. Most commercial TBBPA products consist of a mixture that differ in the degree of bromination with the formula C15H16−xBrxO2 where x = 1 to 4. Its fire-retarding properties correlate with its bromine content. The annual consumption in Europe has been estimated as 6200 tons in 2004. [3]

TBBPA is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone. It is used to prepare fire-resistant polycarbonates by replacing some bisphenol A. A lower grade of TBBPA is used to prepare epoxy resins, used in printed circuit boards. [2]

Structure of copolymer of polycarbonate containing the tetrabrominated monomer TBBPAcopolymer.png
Structure of copolymer of polycarbonate containing the tetrabrominated monomer


Toxicity

A study was published by the European Food Safety Authority (EFSA) in December 2011 on the exposure of TBBPA and its derivatives in food. The study, which examined at 344 food samples from the fish and other seafood food group, concluded that “current dietary exposure to TBBPA in the European Union does not raise a health concern.” EFSA also determined that “additional exposure, particularly of young children, to TBBPA from house dust is unlikely to raise a health concern”. [4]

Some studies suggest that TBBPA may be an endocrine disruptor and immunotoxicant. As an endocrine disruptor, TBBPA may interfere with both estrogens and androgens. [5] Further, TBBPA structurally mimics the thyroid hormone thyroxin (T4) and can bind more strongly to the transport protein transthyretin than T4 does, likely interfering with normal T4 activity. TBBPA likely also suppresses immune responses by inhibiting expression of CD25 receptors on T cells, preventing their activation, and by reducing natural killer cell activity. [6] [7]

A 2013 literature review on TBBPA concludes that TBBPA does not produce “adverse effects that might be considered to be related to disturbances in the endocrine system”. [8] Therefore, in accordance with internationally accepted definitions, TBBPA should not be considered an “endocrine disruptor”. Furthermore, TBBPA is rapidly excreted in mammals and therefore does not have a potential for bioaccumulation. Measured concentrations of TBBPA in house dust, human diet and human serum samples are very low. Daily intakes of TBBPA in humans were estimated to not exceed a few ng/kg bw/day. Exposures of the general population are also well below the derived-no-effect-levels (DNELs) derived for endpoints of potential concern in REACH.

TBBPA degrades to bisphenol A and to TBBPA dimethyl ether, and experiments in zebrafish (Danio rerio) suggest that during development, TBBPA may be more toxic than either BPA or TBBPA dimethyl ether. [9]

Occurrence

TBBPA emits can be found in trace concentration in the hydrosphere, soil, and sediments. [10] It also occurs in sewage sludge and house dust. [11] TBBPA has been the subject of an eight-year evaluation under the EU Risk Assessment procedure which reviewed over 460 studies. The Risk Assessment was published on the EU Official Journal in June 2008. [12] The conclusions of the Risk Assessment were confirmed by the European Commission SCHER Committee (Scientific Committee on Health and Environmental Risks [13] ). TBBPA has been registered under REACH. [14]

See also

Further reading

Related Research Articles

Polybrominated diphenyl ethers or PBDEs, are a class of organobromine compounds that are used as flame retardants. Like other brominated flame retardants, PBDEs have been used in a wide array of products, including building materials, electronics, furnishings, motor vehicles, airplanes, plastics, polyurethane foams, and textiles. They are structurally akin to polychlorinated diphenyl ethers (PCDEs), polychlorinated biphenyls (PCBs) and other polyhalogenated compounds, consisting of two halogenated aromatic rings. PBDEs are classified according to the average number of bromine atoms in the molecule. The health hazards of these chemicals have attracted increasing scrutiny, and they have been shown to reduce fertility in humans at levels found in households. Because of their toxicity and persistence, the industrial production of some PBDEs is restricted under the Stockholm Convention, a treaty to control and phase out major persistent organic pollutants (POPs).

<span class="mw-page-title-main">Flame retardant</span> Substance applied to items to slow burning or delay ignition

The term flame retardants subsumes a diverse group of chemicals that are added to manufactured materials, such as plastics and textiles, and surface finishes and coatings. Flame retardants are activated by the presence of an ignition source and are intended to prevent or slow the further development of ignition by a variety of different physical and chemical methods. They may be added as a copolymer during the polymerisation process, or later added to the polymer at a moulding or extrusion process or applied as a topical finish. Mineral flame retardants are typically additive while organohalogen and organophosphorus compounds can be either reactive or additive.

<span class="mw-page-title-main">Endocrine disruptor</span> Chemicals that can interfere with endocrine or hormonal systems

Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine systems. These disruptions can cause cancerous tumors, birth defects, and other developmental disorders. Found in many household and industrial products, endocrine disruptors "interfere with the synthesis, secretion, transport, binding, action, or elimination of natural hormones in the body that are responsible for development, behavior, fertility, and maintenance of homeostasis ."

<span class="mw-page-title-main">Bisphenol A</span> Chemical compound used in plastics manufacturing

Bisphenol A (BPA) is a chemical compound primarily used in the manufacturing of various plastics. It is a colourless solid which is soluble in most common organic solvents, but has very poor solubility in water. BPA is produced on an industrial scale by the condensation reaction of phenol and acetone. Global production in 2022 was estimated to be in the region of 10 million tonnes.

<span class="mw-page-title-main">Persistent organic pollutant</span> Organic compounds that are resistant to environmental degradation

Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic chemicals that adversely affect human health and the environment around the world. Because they can be transported by wind and water, most POPs generated in one country can and do affect people and wildlife far from where they are used and released.

Brominated flame retardants (BFRs) are organobromine compounds that have an inhibitory effect on combustion chemistry and tend to reduce the flammability of products containing them. The brominated variety of commercialized chemical flame retardants comprise approximately 19.7% of the market. They are effective in plastics and textile applications like electronics, clothes and furniture.

Xenoestrogens are a type of xenohormone that imitates estrogen. They can be either synthetic or natural chemical compounds. Synthetic xenoestrogens include some widely used industrial compounds, such as PCBs, BPA, and phthalates, which have estrogenic effects on a living organism even though they differ chemically from the estrogenic substances produced internally by the endocrine system of any organism. Natural xenoestrogens include phytoestrogens which are plant-derived xenoestrogens. Because the primary route of exposure to these compounds is by consumption of phytoestrogenic plants, they are sometimes called "dietary estrogens". Mycoestrogens, estrogenic substances from fungi, are another type of xenoestrogen that are also considered mycotoxins.

<span class="mw-page-title-main">Hexabromocyclododecane</span> Chemical compound

Hexabromocyclododecane is a brominated flame retardant. It consists of twelve carbon, eighteen hydrogen, and six bromine atoms tied to the ring. Its primary application is in extruded (XPS) and expanded (EPS) polystyrene foam that is used as thermal insulation in the building industry. Other uses are upholstered furniture, automobile interior textiles, car cushions and insulation blocks in trucks, packaging material, video cassette recorder housing and electric and electronic equipment. According to UNEP, "HBCD is produced in China, Europe, Japan, and the USA. The known current annual production is approximately 28,000 tonnes per year. The main share of the market volume is used in Europe and China". Due to its persistence, toxicity, and ecotoxicity, the Stockholm Convention on Persistent Organic Pollutants decided in May 2013 to list hexabromocyclododecane in Annex A to the convention with specific exemptions for production and use in expanded polystyrene and extruded polystyrene in buildings. Because HBCD has 16 possible stereo-isomers with different biological activities, the substance poses a difficult problem for manufacture and regulation.

<span class="mw-page-title-main">Decabromodiphenyl ether</span> Chemical compound

Decabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs). It was commercialised in the 1970s and was initially thought to be safe, but is now recognised as a hazardous and persistent pollutant. It was added to Annex A of the Stockholm Convention on Persistent Organic Pollutants in 2017, which means that treaty members must take measures to eliminate its production and use. The plastics industry started switching to decabromodiphenyl ethane as an alternative in the 1990s, but this is now also coming under regulatory pressure due to concerns over human health.

Pentabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs). Because of their toxicity and persistence, their industrial production is to be eliminated under the Stockholm Convention, a treaty to control and phase out major persistent organic pollutants (POP).

Octabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs).

<span class="mw-page-title-main">Triphenyl phosphate</span> Chemical compound

Triphenyl phosphate (TPhP) is the chemical compound with the formula OP(OC6H5)3. It is the simplest aromatic organophosphate. This colourless solid is the ester (triester) of phosphoric acid and phenol. It is used as a plasticizer and a fire retardant in a wide variety of settings and products.

<span class="mw-page-title-main">Bisphenol S</span> Chemical compound

Bisphenol S (BPS) is an organic compound with the formula (HOC6H4)2SO2. It has two phenol functional groups on either side of a sulfonyl group. It is commonly used in curing fast-drying epoxy resin adhesives. It is classified as a bisphenol, and a close molecular analog of bisphenol A (BPA). BPS differentiates from BPA by possessing a sulfone group (SO2) as the central linker of the molecule instead of a dimethylmethylene group (C 2), which is the case of bisphenol A.

<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

<span class="mw-page-title-main">Tris(1,3-dichloro-2-propyl)phosphate</span> Chemical compound

Tris(1,3-dichloroisopropyl)phosphate (TDCPP) is a chlorinated organophosphate. Organophosphate chemicals have a wide variety of applications and are used as flame retardants, pesticides, plasticizers, and nerve gases. TDCPP is structurally similar to several other organophosphate flame retardants, such as tris(2-chloroethyl) phosphate (TCEP) and tris(chloropropyl)phosphate (TCPP). TDCPP and these other chlorinated organophosphate flame retardants are all sometimes referred to as "chlorinated tris".

Xenohormones or environmental hormones produced outside of the human body which exhibit endocrine hormone-like properties. They may be either of natural origin, such as phytoestrogens, which are derived from plants, or of synthetic origin. These compounds are able to activate the same endocrine receptors as their natural counterparts and are thus frequently implicated in endocrine disruption. The most commonly occurring xenohormones are xenoestrogens, which mimic the effects of estrogen. Other xenohormones include xenoandrogens and xenoprogesterones. Xenohormones are used for a variety of purposes including contraceptive & hormonal therapies, and agriculture. However, exposure to certain xenohormones early in childhood development can lead to a host of developmental issues including infertility, thyroid complications, and early onset of puberty. Exposure to others later in life has been linked to increased risks of testicular, prostate, ovarian, and uterine cancers.

<span class="mw-page-title-main">Bisphenol F</span> Chemical compound

Bisphenol F is an organic compound with the chemical formula (HOC
6H
4)
2CH
2. It is structurally related to bisphenol A (BPA), a popular precursor for forming plastics, as both belong to the category of molecules known as bisphenols, which feature two phenol groups connected via a linking group. In BPF, the two aromatic rings are linked by a methylene connecting group. In response to concern about the health effects of BPA, BPF is increasingly used as a substitute for BPA.

<span class="mw-page-title-main">Health effects of Bisphenol A</span> Controversy centering on concerns about the biomedical significance of bisphenol A (BPA)

Bisphenol A controversy centers on concerns and debates about the biomedical significance of bisphenol A (BPA), which is a precursor to polymers that are used in some consumer products, including some food containers. The concerns began with the hypothesis that BPA is an endocrine disruptor, i.e. it mimics endocrine hormones and thus has the unintended and possibly far-reaching effects on people in physical contact with the chemical.

<span class="mw-page-title-main">Bis(2-ethylhexyl)tetrabromophthalate</span> Chemical compound

Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).

<span class="mw-page-title-main">Gerald A. LeBlanc</span> American biologist, toxicologist, author

Gerald A. LeBlanc is an American biologist, toxicologist, author, and academic. He is a Professor Emeritus in the Department of Biological Sciences at the North Carolina State University.

References

  1. 1 2 3 4 Record of Tetrabromobisphenol A in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2008/2/15.
  2. 1 2 Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405.{{cite encyclopedia}}: CS1 maint: multiple names: authors list (link)
  3. ↑ "RISK ASSESSMENT OF 2,2',6,6'-TETRABROMO-4,4'-ISOPROPYLIDENE DIPHENOL (TETRABROMOBISPHENOL-A)". Environment Agency (UK). June 2007.
  4. ↑ EFSA Scientific Opinion on Tetrabromobisphenol A (TBBPA) and its derivatives in food (2011) https://efsa.onlinelibrary.wiley.com/doi/abs/10.2903/j.efsa.2011.2477. See page 1.
  5. ↑ Shaw, S.; Blum, A.; Weber, R.; Kannan, K.; Rich, D.; Lucas, D.; Koshland, C.; Dobraca, D.; Hanson, S.; Birnbaum, L. (2010). "Halogenated flame retardants: do the fire safety benefits justify the risks?". Reviews on Environmental Health. 25 (4): 261–305. doi:10.1515/REVEH.2010.25.4.261. PMID   21268442. S2CID   20573319.
  6. ↑ Pullen, S; Boecker R.; Tiegs G (2003). "The flame retardants tetrabromobisphenol A and tetrabromobisphenol A–bisallylether suppress the induction of interleukin-2 receptor α chain (CD25) in murine splenocytes". Toxicology. 184 (1): 11–22. doi:10.1016/S0300-483X(02)00442-0. PMID   12505372.
  7. ↑ Kibakaya, EC; Stephen K; Whalen MM (2009). "Tetrabromobisphenol A has immunosuppressive effects on human natural killer cells". Journal of Immunotoxicology. 6 (4): 285–292. doi:10.3109/15476910903258260. PMC   2782892 . PMID   19908946.
  8. ↑ Colnot, Thomas; Kacew, Sam; Dekant, Wolfgang (2013). "Mammalian toxicology and human exposures to the flame retardant 2,2′,6,6′-tetrabromo-4,4′-isopropylidenediphenol (TBBPA): implications for risk assessment". Archives of Toxicology. 88 (3): 553–73. doi:10.1007/s00204-013-1180-8. PMID   24352537. S2CID   15254375.
  9. ↑ McCormick, J; Paiva MS; Häggblom MM; Cooper KR; White LA (2010). "Embryonic exposure to tetrabromobisphenol A and its metabolites, bisphenol A and tetrabromobisphenol A dimethyl ether disrupts normal zebrafish (Danio rerio) development and matrix metalloproteinase expression". Aquatic Toxicology. 100 (3): 255–262. doi:10.1016/j.aquatox.2010.07.019. PMC   5839324 . PMID   20728951.
  10. ↑ Covaci, Adrian; Voorspoels, Stefan; Abdallah, Mohamed Abou-Elwafa; Geens, Tinne; Harrad, Stuart; Law, Robin J. (January 2009). "Analytical and environmental aspects of the flame retardant tetrabromobisphenol-A and its derivatives". Journal of Chromatography A. 1216 (3): 346–363. doi:10.1016/j.chroma.2008.08.035. PMID   18760795.
  11. ↑ Kuch B, Körner W, Hagenmaier H (2001): Monitoring von bromierten Flammschutzmitteln in Fliessgewässern, Abwässern und Klärschlämmen in Baden-Württemberg Archived 2003-12-29 at the Wayback Machine . Umwelt und Gesundheit, Universität Tübingen.
  12. ↑ TBBPA draft RAR
  13. ↑ European Union Risk Assessment Report on TBBPA (2008) http://echa.europa.eu/documents/10162/32b000fe-b4fe-4828-b3d3-93c24c1cdd51
  14. ↑ TBBPA REACH Registration webpage http://echa.europa.eu/web/guest/information-on-chemicals/registered-substances
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