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TETRABROMOBISPHENOL A

CAS NUMBER: 79-94-7

MOLECULAR WEIGHT: 543.87

EC NUMBER: 201-236-9


Tetrabromobisphenol A is a white powder. A monomer for flame-retardant epoxy, polyester and polycarboante resins.
tetrabromobisphenol A is a bromobisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups and the phenyl rings are substituted by bromo groups at positions 2, 2', 6 and 6'. 
Tetrabromobisphenol A is a brominated flame retardant. 
Tetrabromobisphenol A has a role as a flame retardant. 

Tetrabromobisphenol A derives from a bisphenol A.
Tetrabromobisphenol A is a brominated flame retardant. 
The compound is a white solid (not colorless), although commercial samples appear yellow. 
Tetrabromobisphenol A is one of the most common fire retardants.
Tetrabromobisphenol A is one of the most prevalent flame retardants, and is used in plastic paints, synthetic textiles, and electrical devices.

Tetrabromobisphenol A is one of the most prevalent flame retardants, and is used in plastic paints, synthetic textiles, and electrical devices. 
Despite the fact that Tetrabromobisphenol A is excreted quickly from the body, Tetrabromobisphenol A is detected in human plasma and milk. 
Proposition 65 requires businesses to determine if they must provide a warning about exposures to listed chemicals.
Tetrabromobisphenol–A is a brominated organic compound. 

Tetrabromobisphenol A's primary used as an intermediate in the production of flame retardants like PBDEs, but can also be used as a flame retardant itself.
Tetrabromobisphenol A (Tetrabromobisphenol A) is a brominated flame retardant used in flame-retarded epoxy and polycarbonate resins and is currently the highest selling brominated flame retardant globally. 
Resins containing Tetrabromobisphenol A have wide-ranging applications, including communications and electronics equipment, automotive parts, and appliances. 
Tetrabromobisphenol A is not known to have been manufactured in Canada.

Tetrabromobisphenol-A is produced in the USA, Israel and Japan but not in the EU. 
Current production is estimated between 120.000 and 150.000 ton each year, of which approximately 40.000 ton is exported to the European Union.
Tetrabromobisphenol-A is likely to reach the marine environment through industrial waste waters from land-based industrial activities. 
A small contribution may come from releases to the water from losses from products which contain the substance.

There is currently no information on levels of tetrabromobisphenol-A in marine waters, but there are measurements in estuarine sediments and in North Sea biota. 
Concentrations in the Scheldt estuary sediments range between 0,1 and 32 µg/kg wet weight. 
Concentrations in North Sea biota can reach up to 245 µg/kg wet weight in whiting fillet.

Tetrabromobisphenol-A is considered to have a moderate tendency towards bioaccumulation.
Tetrabromobisphenol A, or Tetrabromobisphenol A, is a useful flame retardant used in a variety of consumer products, including electrical equipment and household furniture. 
Organobromide flame retardants such as Tetrabromobisphenol A are widely used due to their efficacy and in order to meet fire safety standards for products on the market, but concerns have been raised due to Tetrabromobisphenol A's ability to leach into the environment and produce adverse effects on human health and ecosystems overall.

Tetrabromobisphenol A has been shown in vitro to bind to estrogen hormone receptors at high concentrations (Gosavi et al., 2013) and cause other effects on hormone sensitive parameters. 
In 2004, Tetrabromobisphenol A had an annual global production of more than 170 kilotons, though only 20-30% of the total volume produced was used as an additive flame retardant on material subject to environmental leaching (ECB, 2006). 
Though the live animal toxicity database on Tetrabromobisphenol A does not suggest that this flame retardant has any substantial impact on systemic effects, including endocrine function, the potential effects of Tetrabromobisphenol A on developmental and reproductive functions have not been examined.
This recent article submitted to the journal Toxicology by Cope et al. (2015) studies the influence of Tetrabromobisphenol A on reproductive and developmental parameters in Sprague-Dawley rats exposed orally at doses up to 1000 mg/kg of body weight daily in two separate, unpublished developmental and multi-generational studies, also examining endocrine function and behavioral, neurological and neuropathic functions in the offspring.
Tetrabromobisphenol A was not found to be a developmental toxicant in rats, showing no signs of adult maternal toxicity or overt teratogenicity. Results from the multigenerational study showed a sole histopathologic alteration in the F2 generation with a thinning of the brain parietal cortex, though this was considered reversible and interpreted with caution, due to no other neurodevelopmental or neurofunctional deficits being noted. Decreases in serum T4 in the thyroid were found with absences of concurrent changes in other thyroid hormones, such as T3 and TSH, leading the authors to conclude that this pattern of change has been seen with other xenobiotics in rodents and has not yet been seen in humans. The authors suggest that this is possibly due to a protein chaperone, thyroxine binding globulin or TBG, not found in rats and thus allowing humans to be more resistant to the effects of Tetrabromobisphenol A on T4. No other effects were noted for Tetrabromobisphenol A in the multi-generational study.

Tetrabromobisphenol A's is a very persistent substance. It's very difficult to be biodegraded in aerobic conditions, while Tetrabromobisphenol A's still rather unknown whether it degrades in anaerobic conditions: Tetrabromobisphenol A has been suggested that under anaerobic conditions TBBT-A may be biodegraded to bisphenol-A.
Tetrabromobisphenol A is a toxic substance as concentrations above 2,6 µg/l might already cause problems at chronic exposure for marine invertebrates. 
Such concentrations might already impair the shell growth of a species of oysters. 
Fresh water invertebrates and fish have a higher tolerance, concentrations of 0,12 and 0,16 mg/l respectively are necessary to cause effects. 
Present marine concentrations are considered to be of little risk to biota, however concern is raised about the possible degradation to biphenol-A, of which low concentrations have been shown to affect the endocrine system.

Tetrabromobisphenol A is used as a reactant and additive flame retardant in plastics, adhesives, paper and textiles and as a plasticizer in electrical and electronic equipment.
Tetrabromobisphenol A is a flame retardant used to reduce the flammability of plastics and synthetic resins in some consumer products.
As of January 2020, California has banned the sale and distribution of new upholstered furniture, replacement components of reupholstered furniture, foam in mattresses, and certain children’s products made for residential use if these products contain more than 0.1% of certain flame retardants, including Tetrabromobisphenol A.
Tetrabromobisphenol A may be released into air, dust, and surfaces in homes, offices, schools, day care centers, and cars from printed circuit boards, casings, and other parts of electrical and electronic equipment.
Infants and young children may be exposed to higher levels of Tetrabromobisphenol A in air, dust and surfaces.  
This is because they often crawl and play on the floor, getting more dust on their hands, and putting their fingers, toys, and other objects in their mouths.
During pregnancy, Tetrabromobisphenol A can pass from mother to baby.
Tetrabromobisphenol A's physicochemical properties suggest that it will partition to all compartments (i.e., water, sediment, and soil), predominantly to sediment and soil through binding to the organic fraction of a particulate matter. 
Available environmental fate studies indicated that Tetrabromobisphenol A is persistent in water (half-life [t1/2] 182 days), soil (t1/2 182 days), and sediment (t1/2 365 days) (Canada, 2013).
Tetrabromobisphenol A lacks functional groups that are expected to undergo hydrolysis.

A number of laboratory studies (ECHA, 2013) showed that it can degrade to bisphenol A under aerobic conditions.
Tetrabromobisphenol A is identified as a persistent, bioaccumulative, and toxic (PBT) compound under the U.S. 
Environmental Protection Agency s Toxic Release Inventory (EPA, 2013). 
Tetrabromobisphenol A was also placed on the State of Washington s Department of Ecology s PBT List (DOC, 2013). 
However, Environment Canada and Health Canada concluded that Tetrabromobisphenol A did not meet their criteria for bioaccumulation (i.e., bioaccumulation factor >5000) (Canada, 2013). 
This conclusion was based on Tetrabromobisphenol A s low bioaccumulation potential from its physicochemical properties (e.g., maximum diameter of 1.3 1.4 nm, ionization at environmentally relevant pH, and variable logKOW), as well as from studies that showed Tetrabromobisphenol A is rapidly metabolized and excreted in aquatic and terrestrial organisms.

Tetrabromobisphenol A (Tetrabromobisphenol A) is a brominated flame retardant (BFR) widely used in electrical and electronic equipment. Tetrabromobisphenol A is the BRF manufactured in the largest quantities (BSEF, 2009a). 
The substance is both used as a reactive and an additive flame retardant.
In additive usage of Tetrabromobisphenol A, the substance is not bound chemically in the polymer material, and therefore continues to exist as the original substance, and has the potential for migrating or evaporating out of the polymer. 
In reactive usage of the substance, the flame retardant is bound chemically into the polymer and does not exist anymore as the monomer substance (except for possible unreacted trace concentrations).

The current description focuses on the additive use of Tetrabromobisphenol A.
Besides the pure Tetrabromobisphenol A, a number of derivatives of Tetrabromobisphenol A are used as additive flame retardants. 
Some are used for the same applications as TBBBA whereas others are mainly used for flame retarding other polymers. 
The Tetrabromobisphenol A derivatives are not included in the present assessment, but a few notes on their application are added for the framing of the description of the use of Tetrabromobisphenol A.
Tetrabromobisphenol A is not produced in the EU. 
Globally Tetrabromobisphenol A is produced in USA, Japan, Jordan and Israel.

BENEFITS AND FEATURES:

Tetrabromobisphenol A is a highly pure flame retardant containing very stable aromatic bromine.
Tetrabromobisphenol A can be used as a reactive or additive flame retardant.
As a reactive flame retardant, TBBA finds particular application as a reactive monomer in epoxy and polycarbonate polymers.
Tetrabromobisphenol A is very cost-effective and once reacted, Tetrabromobisphenol A is permanent and non-migrating.
Tetrabromobisphenol A is a major component in epoxy oligomers used as additives for styrenic polymers and many engineering thermoplastics. 
Properties of note are improved polymer viscosityand UV resistance.


CHEMICAL PROPERTIES:

Tetrabromobisphenol A is a white to pale cream or pale yellow crystalline with a moderately high molecular weight, low water solubility, and moderately high lipophilicity (as indicated by log Kow). Only about 4% of the particles are <15 μm in diameter, and thus, little (<4%) is expected to be respirable (<10 μm in diameter) and absorbed from the lung after inhalation exposure.
Tetrabromobisphenol A (Tetrabromobisphenol A) is a brominated flame retardant used in a variety of reactive and additive applications. 
Tetrabromobisphenol A is reacted (i.e., covalently bound) with epoxy, vinyl esters, and polycarbonate systems (e.g., high impact polystyrene (HIPS), and is used as an additive in acrylonitrile-butadiene-styrene (ABS) thermoplastic resins (Albemarle, 1999). 
Tetrabromobisphenol A's primary application is in printed wire boards (PWBs) as a reactive flame retardant.

USES:

Tetrabromobisphenol A is widely used as a reactive flame retardant to produce a bromine-containing epoxy resin and polycarbonate, and as intermediates for the synthesis of other complex flame retardant, also as an additive flame retardant for ABS, HIPS, unsaturated polyester rigid polyurethane foams, adhesives and coatings.
The primary use of Tetrabromobisphenol A as an additive flame retardant is in enclosures of acrylonitrile butadiene styrene (ABS) (BSEF, 2009b). ABS is widely used for enclosures and structural parts of many types of electronic and electrical equipment.
CEFIC (presentation without date on manufacturer’s website) inform that ABS with Tetrabromobisphenol A is used for personal computers, monitors, notebooks, photocopiers, scanners, cellular phones, industrial and life safety applications, battery housings, smoke alarms and safety lighting.
An American survey found that ABS with Tetrabromobisphenol A was used in 34% of the computer monitors and in 2% of TV back casings.
In flame retarded ABS for enclosures the Tetrabromobisphenol A is typically applied in concentrations of 14-30% with about 4% antimony trioxide as synergist (Lassen et al., 2006). 

A typical loading for V0 grade ABS is 22% (Lassen et al., 2006). 
Traditionally octa-BDE has been the flame retardant of choice for ABS plastic, but after the phase out of octa-BDE, Tetrabromobisphenol A has been one of the main flame retardant for this plastic type.
Some of the Tetrabromobisphenol A derivatives may as well be used in enclosures of ABS, PP and HIPS, but besides the Tetrabromobisphenol A derivatives are widely used in engineering plastics; first of all the thermoplastic polyesters poly(butylene terephthalate) (PBT) and poly(ethylene terephthalate) (PET). 
These plastics are used for more demanding applications in connectors, circuit breakers and similar parts. According to Munro et al. (2004) brominated carbonate oligomers (probably tetrabromobisphenol-A carbonate oligomer) accounted for 44% of the global flame retardant use in thermoplastic polyesters. 
There are currently no commercially mature non-brominated alternatives for the thermoplastic polyesters, but new alternatives have been introduced recently.
The possible applications of Tetrabromobisphenol A in flame retarded parts of EEE are indicated. 
Flame retarded ABS enclosures or structural parts may in principle be found in products within all categories, but the major part is probably used in Category 2 “IT and telecommunication equipment”.


PRODUCTION AND USE:

-Tetrabromobisphenol A is produced by the reaction of bromine with bisphenol A. 
-Most commercial Tetrabromobisphenol A 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 %Br.The annual consumption in Europe has been estimated as 6.200 tons in 2004.
-Tetrabromobisphenol A is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone. 
-Tetrabromobisphenol A is used to prepare fire-resistant polycarbonates by replacing some Tetrabromobisphenol A. 
-A lower grade of Tetrabromobisphenol A is used to prepare epoxy resins, used in printed circuit boards.

USES:

-Tetrabromobisphenol A is primarily used as a reactive flame retardant in epoxy resin circuit boards. 
-Both hydroxyl groups on Tetrabromobisphenol A can be reacted with epichlorohydrin under basic conditions to form the diglycidyl ether, which is widely used in epoxy resin formulations. 
-Tetrabromobisphenol A is also used in polycarbonate and ether polyester resins and is used as a chemical intermediate for the synthesis of tetra-bromobisphenol A allyl ether, -bis(2-hydroxyethyl ether), -carbonate oligomer, and -diglycidyl ether. 
-Tetrabromobisphenol A is also used as a flame retardant in plastics, paper, and textiles, and as a plasticizer in adhesives and coatings. 
-Being covalently bound to the polymer limits exposure to unbound excess chemical used in the manufacturing process.

PHYSICO - CHEMICAL PROPERTIES:

-Tetrabromobisphenol A (Tetrabromobisphenol A; Figure 25.3), the highest volume flame retardant worldwide, is primarily (90%) a reactive BFR covalently bound to the polymer structure and less likely to be released into the environment than are additive flame retardants (Birnbaum and Bergman, 2010). 
-Tetrabromobisphenol A is used mainly for the production of circuit board polymers. 
-Tetrabromobisphenol A is highly lipophilic (log Kow=4.5) and has low water solubility (0.72 mg/mL). 
-Tetrabromobisphenol A has been measured in the air (Zweidinger et al., 1979), soil, and sediment (Watanabe et al., 1983), but is generally not found in water samples. 
-Tetrabromobisphenol A is found in eggs of birds, human milk, and umbilical cord serum. 
-Tetrabromobisphenol A derivatives such as ethers are reported to be biologically active, which also may lead to adverse health effects.


TOXICITY:

A study was published by the European Food Safety Authority (EFSA) in December 2011 on the exposure of Tetrabromobisphenol A 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 Tetrabromobisphenol A in the European Union does not raise a health concern.” 
EFSA also determined that “additional exposure, particularly of young children, to Tetrabromobisphenol A from house dust is unlikely to raise a health concern”.
Some studies suggest that Tetrabromobisphenol A may be an endocrine disruptor and immunotoxicant. 
As an endocrine disruptor, Tetrabromobisphenol A may interfere with both estrogens and androgens. 
Further, Tetrabromobisphenol A 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. 

Tetrabromobisphenol A likely also suppresses immune responses by inhibiting expression of CD25 receptors on T cells, preventing their activation, and by reducing natural killer cell activity.
A 2013 literature review on Tetrabromobisphenol A concludes that Tetrabromobisphenol A does not produce “adverse effects that might be considered to be related to disturbances in the endocrine system”. 
Therefore, in accordance with internationally accepted definitions, Tetrabromobisphenol A should not be considered an “endocrine disruptor”. 
Furthermore, Tetrabromobisphenol A is rapidly excreted in mammals and therefore does not have a potential for bioaccumulation. 
Measured concentrations of Tetrabromobisphenol A in house dust, human diet and human serum samples are very low. Daily intakes of Tetrabromobisphenol A 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.

Tetrabromobisphenol A degrades to bisphenol A and to Tetrabromobisphenol A dimethyl ether, and experiments in zebrafish (Danio rerio) suggest that during development, Tetrabromobisphenol A may be more toxic than either BPA or Tetrabromobisphenol A dimethyl et.
Tetrabromobisphenol A is a brominated flame retardant that has been associated with kidney toxicity in newborn rats. 
Tetrabromobisphenol A is similar in structure to the thyroid hormone T4 and has been found to compete with T4 in binding to proteins in the blood which reduce overall blood serum levels of thyroid hormones.

OCCURENCE:

-Tetrabromobisphenol A emits can be found in trace concentration in the hydrosphere, soil, and sediments. 
-Tetrabromobisphenol A also occurs in sewage sludge and house dust. 
-Tetrabromobisphenol A 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. 
-The conclusions of the Risk Assessment were confirmed by the European Commission SCHER Committee.

SYNONYM:

79-94-7
3,3',5,5'-Tetrabromobisphenol A
4,4'-(propane-2,2-diyl)bis(2,6-dibromophenol)
Bromdian
2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane
4,4'-Isopropylidenebis(2,6-dibromophenol)
Firemaster BP 4A
Tetrabromodian
Tetrabromobisphenol A
Fire Guard 2000
Great Lakes BA-59P
2,2',6,6'-TETRABROMOBISPHENOL A
Saytex RB 100PC
Phenol, 4,4'-(1-methylethylidene)bis[2,6-dibromo-
Tetrabromodiphenylopropane
Firemaster BP4A
FG 2000

IUPAC NAME:

2,2',6,6',-tetrabromo-4,4'-isopropylidenediphenol
2,2',6,6'-Tetrabromo-4,4'-isopropylidenediphenol
2,2',6,6'-tetrabromo-4,4'-isopropylidenediphenol
2,2',6,6'-tetrabromo-4,4'-isopropylidenediphenol
2,2’,6,6’-tetrabromo-4,4’-isopropylidenediphenol
2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenol
4,4'-Isopropylylidenebis(2,6-dibromophenol)
4,4'-propane-2,2-diylbis(2,6-dibromophenol)

TRADE NAME:

AP 1969
CARBONATE OLIGOMER OF TETRABROMOBISPHENOL A
FR-1524
Great Lakes BA-59P
Great Lakes BA-59PC

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