TETRABROMOBISPHENOL A
TETRABROMOBISPHENOL A
IUPAC name: 4,4′-(Propane-2,2-diyl)bis(2,6-dibromophenol)
CAS Number: 79-94-7
EC Number: 201-236-9
Chemical formula: C15H12Br4O2
Molar mass: 543.9 g
Tetrabromobisphenol A (TBBPA) is a brominated flame retardant.
Tetrabromobisphenol A is a white solid (not colorless), although commercial samples appear yellow.
Tetrabromobisphenol A is one of the most common fire retardants.
Tetrabromobisphenol A derives from 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 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.
Production and uses of Tetrabromobisphenol A:
Tetrabromobisphenol is produced by the reaction of bromine with bisphenol A.
Most commercial Tetrabromobisphenol products consist of a mixture that differ in the degree of bromination with the formula C15H16−xBrxO2 where x = 1 to 4.
Tetrabromobisphenol is 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.
Tetrabromobisphenol is mainly used as a reactive component of polymers, meaning that it is incorporated into the polymer backbone.
Tetrabromobisphenol is used to prepare fire-resistant polycarbonates by replacing some bisphenol A.
A lower grade of Tetrabromobisphenol is used to prepare epoxy resins, used in printed circuit boards.
Uses of Tetrabromobisphenol A:
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.
Benefits and Features of Tetrabromobisphenol A:
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.
Properties of Tetrabromobisphenol A:
Density: 2,12 g·cm−3 (20 °C)
Melting point: 178 °C
Boiling point: 250 °C
Solubility in water: Insoluble
XLogP3-AA: 6.8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 2
Exact Mass: 543.75298
Monoisotopic Mass: 539.75708
Topological Polar Surface Area: 40.5 Ų
Heavy Atom Count: 21
Complexity: 3.10
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Properties of Tetrabromobisphenol A:
Tetrabromobisphenol A, 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.
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, 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.
Tetrabromobisphenol A (TBBPA) is one of the most prevalent flame retardants, and is used in plastic paints, synthetic textiles, and electrical devices.
Production volume of Tetrabromobisphenol A:
The production process for tetrabromobisphenol A involves the bromination of bisphenol A in the presence of a solvent, such as methanol, a halocarbon alone, or a halocarbon with water, or 50% hydrobromic acid, or aqueous alkyl monoethers.
Due to the nature of the process and the by-products (e.g. hydrobromic acid and methyl bromide) that can be formed, the production process is largely conducted in closed systems.
Use of Tetrabromobisphenol A:
Approximately 58% of tetrabromobisphenol A is used as a reactive brominated flame retardant in epoxy,polycarbonate and phenolic resins in printed circuit boards, 18% is used for the production of tetrabromobisphenol A derivatives and oligomers, while 18% is used as additive flame retardant in the manufacture of acrylonitrile–butadiene–styrene resins or high impact polystyrene.
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.
Reactive applications of Tetrabromobisphenol A:
Tetrabromobisphenol A is used primarily as an intermediate in the manufacture of polycarbonate unsaturated polyester and epoxy resins, in which it becomes covalently bound in the polymer.
Polycarbonates are used in communication and electronic equipment, electronic appliances, transportation devices, sports and recreational equipment, and lighting fixtures and signs.
Unsaturated polyesters are used in the manufacture of simulated marble floor tiles, bowling balls, furniture, coupling compounds for sewer pipes, buttons, and automotive patching compounds.
Flame-retardant epoxy resins may be used mainly for the manufacture of printed circuit boards.
Moreover, epoxy resins containing tetrabromobisphenol A are used to encapsulate certain electronic components (e.g. plastic/paper capacitors, microprocessors, bipolar power transistors, “integrated gate bipolar transistor power modules” and “application specific integrated circuits” on printed circuit boards).
Additive applications of Tetrabromobisphenol A:
Tetrabromobisphenol A is generally usedwith antimony oxide for optimum performanceas an additive fire retardant that is applied in acrylonitrile–butadiene–styrene resins that are used in automotive parts, pipes and fittings, refrigerators, business machines and telephones, and can also be applied to high-impact polystyrene resins used
in casings of electrical and electronic equipment, furniture, building and construction materials.
The largest additive use of tetrabromobisphenol A is in television casings for which approximately 450 tonnes are used per year.
Other uses include: personal computer monitor casings, components in printers, fax machines and photocopiers, vacuum cleaners, coffee machines and plugs/sockets.
As additive flame retardant, tetrabromobisphenol A does not react chemically with the other components of the polymer, and may therefore leach out of the polymer matrix after incorporation.
Uses of Tetrabromobisphenol A:
Tetrabromobisphenol A (TBBPA) is primarily used as a reactive flame retardant in epoxy resin circuit boards.
Both hydroxyl groups on TBBPA 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.
Tetrabromobisphenol A is an organobromide compound and a brominated flame retardant.
In the reactive application, TBBPA is bound chemically to the polymers.
The main use is epoxy resins of printed circuit boards.
As an additive flame retardant it is used in acrylonitrile butadiene styrene, which is found in products such as TVs.
Bromine is a halogen element with the symbol Br and atomic number 35.
Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.
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 (TBBPA) 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.
Tetrabromobisphenol A is primary application is in printed wire boards (PWBs) as a reactive flame retardant.
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.
Tetrabromobisphenol A (TBBPA) is primarily used as a reactive flame retardant in epoxy resin circuit boards.
Both hydroxyl groups on TBBPA 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.
Tetrabromobisphenol A may be used as an analytical reference standard for the quantification of the analyte in air samples and sediment/sludge samples using chromatography techniques
Tetrabromobisphenol A is an organohalogen flame retardant commonly used as a raw material in the manufacture of printed circuit boards and in the plastic casings around electrical and electronic components.
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.
Uses of Tetrabromobisphenol A:
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.
Synthesis of Tetrabromobisphenol A:
Tetrabromobisphenol A is a derivative of bisphenol A and is synthesized from this substance.
Most commercial Tetrabromobisphenol A products are of a relatively low purity, in fact containing a mixture of products brominated to varying extents.
This is not generally considered to be a drawback, since in most applications of this substance (i.e. flame-retarding) it is the average %Br that is of importance.
The mixture resulting from the bromination of bisphenol A is therefore not purified, allowing a more efficient, lower cost product.
Chemical properties of Tetrabromobisphenol A:
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.
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.
Tetrabromobisphenol A’s primary application is in printed wire boards (PWBs) as a reactive flame retardant.
Consumer Uses of Tetrabromobisphenol A
Tetrabromobisphenol A is used in the following products: polymers.
Other release to the environment of Tetrabromobisphenol A is likely to occur from: outdoor use in close systems with minimal release (e.g. hydraulic liquids in automotive suspension, lubricants in motor oil and break fluids), outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Service life of Tetrabromobisphenol A:
Release to the environment of this Tetrabromobisphenol A can occur from industrial use: industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal) and in the production of articles.
Other release to the environment of Tetrabromobisphenol A is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Tetrabromobisphenol A can be found in complex articles, with no release intended: machinery, mechanical appliances and electrical/electronic products (e.g. computers, cameras, lamps, refrigerators, washing machines).
Tetrabromobisphenol A can be found in products with material based on: plastic (e.g. food packaging and storage, toys, mobile phones).
Tetrabromobisphenol A is used in the following areas: building & construction work.
Other release to the environment of Tetrabromobisphenol A is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Tetrabromobisphenol A is considered to have a moderate tendency towards bioaccumulation.
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.
Formulation or re-packing of Tetrabromobisphenol A:
Tetrabromobisphenol A is used in the following products: polymers.
Tetrabromobisphenol A has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of Tetrabromobisphenol A can occur from industrial use: formulation in materials, in the production of articles, in processing aids at industrial sites and for thermoplastic manufacture.
Uses at industrial sites of Tetrabromobisphenol A:
Tetrabromobisphenol A is used in the following products: polymers.
Tetrabromobisphenol A has an industrial use resulting in manufacture of another substance (use of intermediates).
Tetrabromobisphenol A is used in the following areas: formulation of mixtures and/or re-packaging.
Tetrabromobisphenol A is used for the manufacture of: plastic products, chemicals, electrical, electronic and optical equipment and machinery and vehicles.
Release to the environment of Tetrabromobisphenol A can occur from industrial use: in the production of articles, for thermoplastic manufacture, as processing aid and in processing aids at industrial sites.
Synonmys:
Tetrabromobisphenol A
79-94-7
3,3′,5,5′-Tetrabromobisphenol A
Bromdian
4,4′-(propane-2,2-diyl)bis(2,6-dibromophenol)
4,4′-Isopropylidenebis(2,6-dibromophenol)
2,2-Bis(3,5-dibromo-4-hydroxyphenyl)propane
Firemaster BP 4A
Tetrabromodian
TBBPA
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
2,6-dibromo-4-[2-(3,5-dibromo-4-hydroxyphenyl)propan-2-yl]phenol
4,4′-propane-2,2-diylbis(2,6-dibromophenol)
UNII-FQI02RFC3A
4,4′-(1-Methylethylidene)bis(2,6-dibromophenol)
BA 59
3,5,3′,5′-Tetrabromobisphenol A
NSC 59775
Saytex RB-100
4,4′-Isopropylylidenebis(2,6-dibromophenol)
2,2-Bis(4-hydroxy-3,5-dibromophenyl)propane
FQI02RFC3A
CHEMBL184450
DTXSID1026081
CHEBI:33217
Phenol, 4,4′-isopropylidenebis(2,6-dibromo-
Phenol, 4,4′-isopropylidenebis[2,6-dibromo-
4,4′-(2,2-propanediyl) bis[2,6-dibromo]phenol
MFCD00013962
Phenol, 4,4′-(1-methylethylidene)bis(2,6-dibromo-
FR-1524
DSSTox_CID_6081
DSSTox_RID_78008
DSSTox_GSID_26081
2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)-1-methylethyl]phenol
CAS-79-94-7
CCRIS 6274
Tetrabromo bisphenol A
HSDB 5232
4,4′-(1-methylethylidene)bis[2,6-dibromophenol]
EINECS 201-236-9
3,3′,5,5′-Tetrabromo bisphenol A
FLAME CUT 120G
2,2′,6,6′-Tetrabromo-4,4′-isopropylidenediphenol
4,4′-(2,2-PROPANEDIYL)BIS(2,6-DIBROMOPHENOL)
33’55’-Tetrabromobisphenol A
3osw
XDI
4,6-dibromophenol)
Saytex RB-100 ABS
2,5-dibromophenyl)propane
TETRABROMO-4,4′-ISOPROPYLIDENEDIPHENOL
bmse000567
Tetrabromobisphenol ”A”
EC 201-236-9
4,4′-(1-Methylethylidene)bis(2,6-dibromophenol)2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane
Oprea1_822733
SCHEMBL18647
MLS002152878
BIDD:ER0631
C15H12Br4O2
330396_ALDRICH
2,6,6′-Tetrabromobisphenol A
3,3′,5′-Tetrabromobisphenol A
ALBB-031649
NSC59775
ZINC1689786
Tox21_201182
Tox21_201981
Tox21_300561
2,5-dibromo-4-hydroxyphenyl)propane
BDBM50150793
BR1202
c0763
NSC-59775
STK048486
ZINC01689786
2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxy-phenyl)-1-methyl-ethyl]phenol
AKOS000491577
2,2”,6,6”-Tetrabromobisphenol A
3,3”,5,5”-tetrabromobisphenol A
3,3\’,5,5\’-tetrabromobisphenol A
MCULE-8578472069
NCGC00091463-01
NCGC00091463-02
NCGC00091463-03
NCGC00091463-04
NCGC00091463-05
NCGC00091463-06
NCGC00254356-01
NCGC00258734-01
NCGC00259530-01
AC-11719
AS-12834
SMR001224492
Phenol,4′-isopropylidenebis[2,6-dibromo-
3,3′,5,5′-Tetrabromobisphenol A, 97%
phenol, 4,4′-isopropylidenebis (dibromo-)
2,2-bis(3,5dibromo-4-hydroxyphenyl)propane
4,4”-Isopropylidenebis(2,6-dibromophenol)
4,4′-isopropylidene-bis(2,6-dibromophenol)
FT-0617111
FT-0682679
T0032
2,2-bis(3,5-dibromo-4-hydroxyphenyl)-propane
2,2-bis-(3,5-dibromo-4-hydroxyphenyl)propane
S12384
Tetrabromobisphenol A 50 microg/mL in Methanol
2,2,6,6-Tetrabromo-4,4-Isopropylidene Phenol
2,2-bis-(3,5-dibromo-4-hydroxyphenyl)-propane
A864777
Phenol,4′-(1-methylethylidene)bis[2,6-dibromo-
Q425246
SR-01000596914
Tetrabromodian: tetrabromodihydroxy diphenylpropane
4,4”-(1-Methylethylidene)bis(2,6-dibromophenol)
4,4”-(2,2-propanediyl) bis[2,6-dibromo]phenol
4,4”-(propane-2,2-diyl)bis(2,6-dibromophenol)
SR-01000596914-1
W-104257
2,2′,6,6′-Tetrabromo-4,4′-isopropylidene bisphenol
2,2-bis-(4′-hydroxy-3′,5′-dibromophenyl)-propane
3,3′,5,5′-Tetrabromobisphenol A, analytical standard
Phenol, 4,4′-isopropylidenebis(2,6-dibromo- (8CI)
3,3′,5,5′-Tetrabromo-4,4-dihydroxy-2,2-diphenylpropane
3,3′,5,5′-Tetrabromo-4,4′-dihydroxy-diphenyl-dimethyl-methane
3,3′,5,5′-Tetrabromobisphenol A, certified reference material, TraceCERT(R)