테트라브로모비스페놀 A

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company; Contaminated packaging: Dispose of as unused product.

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Precautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed.

Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection: Handle with gloves.

Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place.

Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Composite samples of human hair collected from barber shops in El Dorado and Magnolia, Arkansas contained 2,2',6,6'-tetrabromobisphenol A at concentrations of up to 2 to 5 ug/kg(1). A French monitoring study conducted during 2004-2006 analyzed samples of maternal and cord serum, adipose tissue and breast milk of 93 women during caesaren births(2); 2,2',6,6'-tetrabromobisphenol A was detected 44% breast milk samples at concentrations of 0.06 to 37.34 ng/g lipid wt, but no detections in adipose tissue(2); positive detections were made in serum samples with average concentrations of 154-199 pg/g fresh wt(2).

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Combined toxicity and oxidative stress biomarker responses were determined for tetrabromobisphenol A (TBBPA) and sulfadiazine (SDZ) to the unicellular green alga Scenedesmus obliquus. Concentration-response analyses were performed for single toxicants and for mixtures containing TBBPA and SDZ with two different mixture ratios. The effect concentrations and the observed effects of the mixtures were compared to the predictions of the joint toxicity by the concentration addition (CA) model and independent action (IA) model. Results showed that the observed joint toxicity was within the scope of the highest (TBBPA) and lowest (SDZ) toxicity observed for the individual components. Furthermore, co-exposure of S. obliquus to TBBPA and SDZ provided preliminary evidence that the mixtures induced oxidative stress leading to cell damage. The CA and IA models proved to be valid for the prediction of the joint toxicity of TBBPA and SDZ. This study highlights a combined environmental risk assessment for two emerging pollutants.

BACKGROUND: Humans are commonly exposed to multiple environmental chemicals, including tetrabromobisphenol A (TBBPA; a flame retardant), triclosan (an antimicrobial agent), and bisphenol A (BPA; polycarbonate plastics). These chemicals are readily absorbed and may interact with each other. OBJECTIVES: We sought to determine whether TBBPA, given alone or in combination with triclosan, can modulate the concentrations of BPA and 17beta-estradiol (E2). METHODS: Female and male CF-1 mice were each given a subcutaneous injection of 0-27 mg TBBPA, with or without concurrent 0.33 mg triclosan, followed by dietary administration of 50 ug/kg body weight (14)C-BPA. Radioactivity was measured in blood serum and tissues through liquid scintillation counting. In subsequent experiments, female and male CF-1 mice were each given a subcutaneous injection of 0 or 1mg TBBPA and E2 was measured in urine 2-12 hr after injection. RESULTS: Doses as low as 1 mg TBBPA significantly elevated (14)C-BPA concentrations in the uterus and ovaries of females; in the testes, epididymides, vesicular-coagulating glands, and preputial glands of males; and in blood serum, heart, lungs, and kidneys of both sexes; urinary E2 concentrations were also elevated. Lower doses of TBBPA or triclosan that had no effects on their own elevated (14)C-BPA concentrations when the two substances were given concurrently. CONCLUSION: These data indicate that TBBPA, triclosan, and BPA interact in vivo, consistent with evidence that TBBPA and triclosan inhibit enzymes that are critical for BPA and E2 metabolism.

Cadmium (Cd) and tetrabromobisphenol A (TBBPA) are two prevalent contaminants in e-waste recycling facilities. However, the potential adversely health effect of co-exposure to these two types of pollutants in an occupational setting is unknown. In this study, we investigated co-exposure of these two pollutants on hepatic toxicity in CD-1 male mice through a whole-body aerosol inhalation route. Specifically, mice were exposed to solvent control (5% DMSO), Cd (8 ug/cu m), TBBPA (16 ug/cu m) and Cd/TBBPA mixture for 8 hr/day and 6 days a week for 60 days. Hepatic changes include increased organ weight, focal necrosis, and elevated levels of liver enzymes in serum. These changes were most severe in mice exposed to TBBPA, followed by Cd/TBBPA mixture and Cd. These chemicals also led to suppressed antioxidant defensive mechanisms and increased oxidative stress. Further, these chemicals induced gene expression of apoptosis-related genes, activated genes encoding for phase I detoxification enzymes and inhibited genes encoding for phase II detoxification enzymes. These findings indicate that the hepatic damages induced by subchronic aerosol exposure of Cd and TBBPA may result from the oxidative damages caused by excessive ROS production when these chemicals were metabolized in the liver.

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

LC50; Species: /Lepomis macrochirus/ (Bluegill sunfish); Concentration: 0.51 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50; Species: /Oncorhynchus mykiss/ (rainbow trout); Concentration: 0.40 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

EC50; Species: Thalassiosira pseudonana (Diatom) 4.7X10+4 cells/mL; Conditions: saltwater, static, pH 8.2; Concentration: 1000 ug/L for 72 hr; Effect: population change /formulation/

EC50; Species: Thalassiosira pseudonana (Diatom) 4.7X10+4 cells/mL; Conditions: saltwater, static, pH 7.6; Concentration: 110 ug/L for 72 hr; Effect: population change /formulation/

For more Ecotoxicity Values (Complete) data for 2,2',6,6'-Tetrabromobisphenol A (21 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.7X10+5(SRC), determined from a structure estimation method(2), indicates that 2,2',6,6'-tetrabromobisphenol A is expected to be immobile in soil(SRC). The pKa1 and pKa2 of 2,2',6,6'-tetrabromobisphenol A are 7.5 and 8.5 respectively(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of 2,2',6,6'-tetrabromobisphenol A from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 4.68X10-8 mm Hg(5), and water solubility, 0.171 mg/L(6). 2,2',6,6'-Tetrabromobisphenol A is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC). Anaerobic biodegradation of 2,2',6,6'-tetrabromobisphenol A has been shown to occur in soil and sediment studies with primary degradation being nearly complete within 10-64 days in some tests(7-9). Anaerobic biodegradation occurs through a biodehalogenation through tri- and dibromobisphenol A with a final product of bisphenol A(8,9). Aerobic biodegradation in soil can also occur(10,11). Aerobic degradation in a Chinese sandy soil under static incubation for 143 days resulted in a half-life of 14.7 days(10). Other studies in aerobic soils have reported half-lives ranging from 9 to 93 days(11). Results of aqueous photolysis studies(12) suggest that direct photolysis may occur on soil surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.7X10+5(SRC), determined from a structure estimation method(2), indicates that 2,2',6,6'-tetrabromobisphenol A is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.0X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 4.68X10-8 mm Hg(4) and water solubility, 0.171 mg/L(5). According to a classification scheme(6), BCF values ranging from 30 to 485(7,8) suggest the potential for bioconcentration in aquatic organisms is moderate to high. Anaerobic biodegradation of 2,2',6,6'-tetrabromobisphenol A has been shown to occur in sediment studies with primary degradation being nearly complete within 55 days(9) and 80% degradation in 10 days of incubation(10). Other studies in anaerobic sediments have reported half-lives ranging from 5 to >130 days(11). Anaerobic biodegradation occurs through a biodehalogenation through tri- and dibromobisphenol A with a final product of bisphenol A(9-11). Aerobic biodegradation may also occur based on a sediment/water study reporting half-lives from 48 to 84 days(12). Phototransformation studies of 2,2',6,6'-tetrabromobisphenol A in aqueous solution determined a UV absorption maximum at 310 nm, a quantum yield of 0.042 and decomposition rates ranging from 3.3X10-5 (at pH 5.5) to 6.8X10-4 (at pH 9) per second which correspond to a half-life range 17 minutes to 5.8 hours(13). 2,2',6,6'-Tetrabromobisphenol A is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Phenols can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl (OH), peroxy (RO2) radicals and singlet oxygen with a half-live on the order of weeks at the water surface(14); therefore, photo-oxidation may have some importance as a fate process for 2,2',6,6'-tetrabromobisphenol A in natural water(SRC).

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Compound with “fair evidence” of ototoxicity (it is a suspected ototoxic substance).

2,2',6,6'-Tetrabromobisphenol A concentrations varying from 0.06 to 37.34 ng/g were detected in breast milk samples collected from 93 volunteers in France between 2004 and 2006(1); 44% of all samples collected contained detectable levels(1). Breast milk samples collected from 10 volunteers in Birmingham, UK during 12 months of lactation (2010 to 2011) had a detection frequency of 61% with concentrations of 0.03-0.17 ng/g lipid wt (5th to 95th percentile) and an average concentration of 0.06 ng/g(2). A few studies demonstrate the presence of TBBPA in breast milk, with average levels between 0.06 and 4.11 ng/g fat, suggesting that milk represents a substantial route of excretion for TBBPA in humans(3).

IDENTIFICATION AND USE: 2,2',6,6'-Tetrabromobisphenol A (TBBPA) is a white crystalline powder. It is primarily used as a reactive flame retardant in epoxy resin circuit boards and more recently in electronic enclosures made of polycarbonate-acrylonitrile-butadiene-styrene (PC-ABS); approximately 90% is used in the manufacture of the resins. HUMAN STUDIES: TBBPA did not produce skin irritation nor contact sensitization. TBBPA was negative for the induction of structural and numerical chromosome aberrations in the in vitro chromosome aberration test using human peripheral lymphocytes. ANIMAL STUDIES: In a 90-day oral study, no toxicity was found in rats treated with up to 100 mg/kg in the feed. A study performed in 3 week old mice treated with a single oral dose (gavage) of 0.1, 5 or 250 mg TBBPA/kg bw showed behavioral alterations in the open field, contextual fear conditioning and Y maze tests 3 hours after dosing. Effects were observed at the two lower doses and not at the highest dose. In a two generation study, rats were administered TBBPA by gavage at 10, 100 or 1,000 mg/kg bw per day from pre-mating until the end of the lactation. The behavioral testing included locomotor activity (horizontal and vertical), and learning and memory tests in the Morris water maze and passive avoidance test. There were no differences in the F2 pups between exposed and control animals. In Xenopus laevis metamorphosis TBBPA exhibits an antagonistic activity at the developmental stages when animals have high endogenous thyroid hormone (TH) levels, whereas it acts as an agonist at the developmental stages when animals have low endogenous TH levels. Some oral toxicity studies in rodents with TBBPA reported changes in thyroid hormone levels and a carcinogenicity study with TBBPA showed increased incidences of uterine tumors in rats. TBBPA may increase levels of circulating estrogens by a competitive inhibition of estrogen conjugation. TBBPA was examined for mutagenic activity at concentrations of 0.001, 0.003, 0.01, 0.03, and 0.1 mg/plate in a series of in vitro microbial assays using Salmonella typhimurium TA1535, TA1537, TA1538, TA98, and TA100 and Saccharomyces cerevisiae with, and without metabolic activation. All tests were negative. ECOTOXICITY STUDIES: TBBPA shows high acute toxicity to aquatic organisms at high concentrations. TBBPA induced oxidative stress in livers of Carassius auratus. TBBPA exposure affected the behavior of zebrafish. Assessed by growth inhibition and the changes at mRNA levels of encoding genes in earthworms, TBBPA showed the greatest toxicity compared to other brominated flame retardants. TBBPA treatment reduced the chlorophyll content and induced production of malondialdehyde in soybean leaves.

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Based on the 5th Chinese Total Diet Study (TDS) carried out in 2011, the average estimated daily intake of 2,2',6,6'-tetrabromobisphenol A via food consumption for a "standard Chinese man" was 1.34 ng/kg bw/day(1); meat and meat products were found to be the major contributor to the daily dietary intake because the consumption of meat and meat products were significantly higher than that of other food groups in China(1).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Tetrabromobisphenol A is included on this list. Effective date: 6/20/85; Sunset date: 6/20/95.

Used as a flame retardant additive to plastics (ABS, phenolic, unsaturated polyester resins, and epoxy resin circuit boards), paper, and textiles; Also used as a plasticizer and chemical intermediate; [HSDB]

Semiconductor Manufacturing [Category: Industry]

Primarily used as a reactive flame retardant in epoxy resin circuit boards and more recently in electronic enclosures made of polycarbonate-acrylonitrile-butadiene-styrene (PC-ABS); approximately 90% is used in the manufacture of the resins. In encapsulations for integrated circuit chips, 2,2',6,6'-tetrabromombisphenol A (TBBPA) is incorporated into the epoxy polymer structure after curing, resulting in no free TBBPA in the finished product. In addition to its use in polymers, general applications include its use as a flame retardant for plastics, paper, and textiles; as a plasticizer; in adhesives and coatings; and as a chemical intermediate for the synthesis of other flame retardants. It has also been used as a fire-retardant additive and as a fire-retardant polycarbonate comonomer. Additionally, TBBPA is applied to carpeting and office furniture.[NIEHS; Tetrabromobisphenol A

Reproductive effector.

TBBPA and its derivatives are a widely used group of flame retardants. TBBPA is primarily used as a reactive flame retardant, covalently bound to epoxy and polycarbonate resins. It is also used as an additive flame retardant in the manufacture of acrylonitrile butadiene styrene (ABS) resins, high impact polystyrene (HIPS) and phenolic resins. TBBPA derivatives may be used as either reactive or additive intermediates in polymer manufacture.

Used as a chemical intermediate for the synthesis of: tetrabromobisphenol A allyl ether; tetrabromobisphenol A bis(2-hydroxyethyl ether); tetrabromobisphenol A carbonate oligomer; tetrabromobisphenol A diglycidyl ether.

2023: 10,000,000 - <50,000,000 lb

2,2',6,6'-Tetrabromobisphenol A is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#5296]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2,2',6,6'-Tetrabromobisphenol A. Aggregated National Production Volume: 100 to < 500 million pounds.

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2,2',6,6'-Tetrabromobisphenol A:

TBBPA is produced 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 or with water, 50% hydrobromic acid or aqueous alkyl mono ethers. When methanol is used as the solvent, methyl bromide is formed as a by-product. The production process is largely conducted in closed systems.

In the typical batch reaction, bromine in slight excess is added to a stirred bisphenol-A solution in methanol in a suitable reactor at 25-30 °C. The exothermic reaction is controlled by the rate of bromine addition, which is dependent on the refrigeration capacity of the reactor cooling system. After bromine addition, the contents of the reactor are heated to reflux (65 °C) for a short period to allow the slower reaction between methanol and dissolved HBr to occur. During this postreaction period, methyl bromide and some HBr are vented through the overhead condenser system into a series of scrubbers that neutralize and dry methyl bromide, which is produced in about 60% yield based on byproduct HBr. Water is then added to precipitate TBBPA and the resulting slurry is cooled, filtered, washed, and dried. The yield of TBBPA is generally 94-97% based on bisphenol-A.

Commercial TBBPA is available in two grades, an epoxy resin grade and a higher quality polycarbonate grade.

The purity of commercial TBBPA is 98.5% containing 0.1% water, a maximum of 60 mg hydrolysable bromine/kg, and a maximum of 100 mg ionic bromide/kg.

Trade Names: Great Lakes BA-59P; Saytex RB-100; Saytex RB-100 ABS; FR-1524; Bromdian; FG 2000; Fire Guard 2000; Firemaster BP 4A; Tetrabrom

Plastics -> Flame retardants

Plastics -> Polymer Type -> Polyolefin-I; Polyolefin-II; ABS

Adhesive Manufacturing

Phenol, 4,4'-(1-methylethylidene)bis[2,6-dibromo-: ACTIVE

Tetrabromobisphenol-A is produced in the USA, Israel and Japan but not in the EU.