79-94-7 Usage
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 (TBBPA) is a brominated flame retardant used in a variety of reactive and additive applications. It 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). Its primary application is in printed wire boards (PWBs) as a reactive flame retardant (BSEF, 2012).
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.
Definition
ChEBI: 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'. It is a brominated flame retardant. It is a brominated flame retardant and a bromobisphenol. It is functionally related to a bisphenol A.
Preparation
Tetrabromobisphenol A is prepared by the bromination of bisphenol A in the presence of a solvent. This reaction may be conducted:in the presence of a hydrocarbon solvent only orwith water, 50 % hydrobromic acid or aqueous alkyl monoethers.when methanol is used as the solvent, methyl bromide is formed as a by-product. The production process is largely conducted in closed systems (WHO/IPCS, 1995).
Application
The main use of TBBPA is as a reactive flame retardant in epoxy resins for printed circuit boards in computers, telecommunications equipment, industrial controls and automotive electronics. 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. TBBPA 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. TBBPA 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.
General Description
White powder. A monomer for flame-retardant epoxy, polyester and polycarboante resins.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Tetrabromobisphenol A is monomer.
Hazard
Moderately toxic by inhalation and skincontact. An eye irritant.
Fire Hazard
Tetrabromobisphenol A is nonflammable.
Flammability and Explosibility
Nonflammable
Environmental Fate
Its 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 TBBPA is persistent in water (half-life [t1/2] 182 days), soil (t1/2 182 days), and sediment (t1/2 365 days) (Canada, 2013).It lacks functional groups that are expected to undergo hydrolysis (Canada, 2013). A number of laboratory studies (ECHA, 2013) showed that it can degrade to bisphenol A under aerobic conditions (Canada, 2013).
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). It 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 TBBPA did not meet their criteria for bioaccumulation (i.e., bioaccumulation factor >5000) (Canada, 2013). This conclusion was based on TBBPA 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 TBBPA is rapidly metabolized and excreted in aquatic and terrestrial organisms (Canada, 2013).
Toxicity evaluation
Tetrabromobisphenol A (TBBPA) is a brominated flame retardant that has been associated with kidney toxicity in newborn rats. TBBPA 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.Tetrabromobisphenol A is classified as hazard statements (H) H400/H410, which means that it is toxic to aquatic biota, causing long-term changes in these organisms.TBBPA is included on Washington State's PBT (Persistent, Bioaccumulative and Toxic) Rule of chemicals.TBBPA is on the Proposition 65 list because it can cause cancer.A National Toxicology Program two-year bioassay study reported that there was clear cancer development in female rats that were exposed to TBBPA, and some evidence in male mice.
Check Digit Verification of cas no
The CAS Registry Mumber 79-94-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 79-94:
(4*7)+(3*9)+(2*9)+(1*4)=77
77 % 10 = 7
So 79-94-7 is a valid CAS Registry Number.
InChI:InChI=1/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
79-94-7Relevant articles and documents
Instantaneous, facile and selective synthesis of tetrabromobisphenol a using potassium tribromide: An efficient and renewable brominating agent
Kumar, Lalit,Sharma, Vivek,Mahajan, Tanu,Agarwal
, p. 174 - 179 (2010)
An instantaneous method for the bromination of bisphenol A has been reported using potassium tribromide for the first time as an efficient brominating agent affording the corresponding tetrabromobisphenol A in a reaction time of only 5 - 10 min at ambient temperature in high yields (99%) and purity (>99%), free from reaction byproduct and having very low ionic impurities. Mild reaction conditions and simple workup provide a practical and commercially viable route for the synthesis of the largest selling flame retardant. The generated HBr during the bromination reaction is used either in the preparation of value-added brominated products or is disposed of as waste, causing serious environmental problems. An environmentally acceptable method for an inbuilt recycling of HBr by its neutralisation, thereby generating additional amounts of metal bromide and recovering the solvent from the liquid mixture has been designed and developed. The KBr used for the preparation of potassium tribromide can be recovered, regenerated in additional amounts, and reused without any significant loss.
Electrochemical synthesis of quinones and other derivatives in biphasic medium
Shanmugam,Kulangiappar,Ramaprakash,Vasudevan,Senthil Kumar,Velayutham,Raju
, p. 2294 - 2297 (2017/05/19)
Electrochemical synthesis of quinones has been attempted from phenols, 1,4-dihydroxybenzenes, 1,4-dihydroxynaphthalenes and related compounds using biphasic media. Excellent yields of quinones (98%) or brominated diols have been achieved with good current efficiency. Reuse of the electrolyte without any modification and quantitative conversion of substrate with theoretical amount of current are the advantages of this method.
Supramolecular organic frameworks of brominated bisphenol derivatives with organoamines
Lue, Jian,Han, Li-Wei,Lin, Jing-Xiang,Cao, Rong
experimental part, p. 3551 - 3557 (2012/03/27)
Reactions of two brominated bisphenol derivatives, tetrabromobisphenol-F (TBBPF) and tetrabromobisphenol-A (TBBPA), with various organoamines resulted in six supramolecular organic frameworks (SOFs), formulated as (TBBPF 2-)2·(HPZ+)2· (H 2PZ2+) (1), (TBBPF-)2· (H2PZ2+)·2H2O·2MeOH (2), (TBBPF) · (TBBPF-)· (HDABCO+)·H2O (3), (TBBPF) · (HMTA) (4), (TBBPA) · (HMTA) (5), and (TBBPA) 3· (HMTA)3·H2O (6) (PZ = piperazine; DABCO = diazabicyclo[2.2.2]octane; HMTA = hexamethylenetetramine). Compounds 1-6 were characterized by single-crystal and powder X-ray diffractions. The predominant driving forces in 1-6 are hydrogen bonds (H-bonds), by which the compounds assemble into supramolecular organic frameworks with versatile topological structures. Compound 1 contains TBBPF/PZ in a 2:3 ratio and exhibits 2D (two-dimensional) H-bonded supramolecular 4 4-sql layer structure built by the four-connected {H 2PZ2+} moieties and {TBBPF2-}. Compound 2 shows a 2-fold interpenetrated 3D (three-dimensional) H-bonded networks comprised by TBBPF/PZ in 2:1 ratio with the presence of solvent H2O and MeOH molecules, in which two identical pcu topological nets are recognized by choosing a decamer synthons as nodes. Compound 3 displays H-bonded 4 4-sql layer structure built by 2:1 TBBPF and DABCO, as well as one H2O per formula unit. Compounds 4 and 5 assemble into 1D (one-dimensional) H-bonded zigzag chains via the alternate linkage of HMTA with TBBPF/TBBPA in a similar fashion. Compound 6 generates an interesting hexamer subunit (HMTA ...TBBPA ...HMTA ...TBBPA ...HMTA...TBBPA), which can be viewed as a fragment of three repeating units for a zigzag chain observed in compound 5. A pair of the hexamer subunits is further connected by two water molecules to form an H-bonded molecular oligomer. Importantly, halogen bonds (X-bonds) have been observed in compounds 4-6 that exhibit 1D and 0D H-bonded supramolecular structures.