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IUPAC name 1,1'-ethane-1,2-diylbis(pentabromobenzene) | |
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ChemSpider | |
ECHA InfoCard | 100.076.669 |
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CompTox Dashboard (EPA) | |
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Properties | |
C14H4Br10 | |
Molar mass | 971.226 g·mol−1 |
Appearance | White solid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Decabromodiphenyl ethane is a chemical compound used as a brominated flame retardant. It was commercialised in the 1990s as an alternative for decabromodiphenyl ether, [1] following safety concern over that compound. The two molecules are chemically very similar, which gives them a similar application profile. Decabromodiphenyl ethane is now also coming under regulatory pressure. [2]
Decabromodiphenylethane is used as a flame retardant in a wide variety of materials including high-impact polystyrene (HIPS), acrylonitrile butadiene styrene (ABS), polyolefins and elastomers. Antimony trioxide is often included as a synergist. Its use in epoxy resins (used for circuit boards), HIPS and ABS (casings), wire and cable means that it is common in electronic devices. [3] The amount manufactured in China between 2006 and 2016 was 230,000 tons, of which 39,000 tons were exported from China in electrical appliances. [4] Under the REACH Regulation, it is registered for the manufacture in and/or the import to the European Economic Area in the tonnage band between 10 000 and 100 000 tonnes per year. [2] In e-waste, an average concentration of 340±200 ppm was found in a study conducted in 2011, confirming the widespread occurrence of the chemical in electronic equipment. [5]
Decabromodiphenylethane was first detected in the environment in 2004. [6] It has been found in biota, air, [7] sediments, [8] sewage sludge, [1] and house dust. [9]
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).
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.
In organic chemistry, organophosphates are a class of organophosphorus compounds with the general structure O=P(OR)3, a central phosphate molecule with alkyl or aromatic substituents. They can be considered as esters of phosphoric acid.
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.
Polybrominated biphenyls (PBBs), also called brominated biphenyls or polybromobiphenyls, are a group of manufactured chemicals that consist of polyhalogenated derivatives of a biphenyl core. Their chlorine analogs are the PCBs. While once widely used commercially, PBBs are now controlled substances under the Restriction of Hazardous Substances Directive, which limits their use in electrical and electronic products sold in the EU.
Decamethylcyclopentasiloxane, also known as D5 and D5, is an organosilicon compound with the formula [(CH3)2SiO]5. It is a colorless and odorless liquid that is slightly volatile.
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.
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).
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.
Diphenyl ether is the organic compound with the formula (C6H5)2O. It is a colorless, low-melting solid. This, the simplest diaryl ether, has a variety of niche applications.
Dechlorane plus is a polychlorinated flame retardant produced by Oxychem.
Chlorinated polycyclic aromatic hydrocarbons (Cl-PAHs) are a group of compounds comprising polycyclic aromatic hydrocarbons with two or more aromatic rings and one or more chlorine atoms attached to the ring system. Cl-PAHs can be divided into two groups: chloro-substituted PAHs, which have one or more hydrogen atoms substituted by a chlorine atom, and chloro-added Cl-PAHs, which have two or more chlorine atoms added to the molecule. They are products of incomplete combustion of organic materials. They have many congeners, and the occurrences and toxicities of the congeners differ. Cl-PAHs are hydrophobic compounds and their persistence within ecosystems is due to their low water solubility. They are structurally similar to other halogenated hydrocarbons such as polychlorinated dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and polychlorinated biphenyls (PCBs). Cl-PAHs in the environment are strongly susceptible to the effects of gas/particle partitioning, seasonal sources, and climatic conditions.
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".
Susan D. Shaw was an American environmental health scientist, marine toxicologist, explorer, ocean conservationist, and author. A Doctor of Public Health, she was a professor in the Department of Environmental Health Sciences at the School of Public Health at the State University of New York at Albany, and Founder/President of the Shaw Institute, a nonprofit scientific institution with a mission to improve human and ecological health through innovative science and strategic partnerships. Shaw is globally recognized for pioneering high-impact environmental research on ocean pollution, climate change, oil spills, and plastics that has fueled public policy over three decades. In 1983, with landscape photographer Ansel Adams, she published Overexposure, the first book to document the health hazards of photographic chemicals. Shaw is credited as the first scientist to show that brominated flame retardant chemicals used in consumer products have contaminated marine mammals and commercially important fish stocks in the northwest Atlantic Ocean. She became the first scientist to dive into the Gulf of Mexico oil slick following the 2010 BP Deepwater Horizon oil rig explosion to investigate the impacts of chemical dispersants used in response to the spill.
The Shaw Institute, formerly the Marine & Environmental Research Institute, is a 501(c)(3) nonprofit scientific research organization based in Blue Hill, Maine and New York City. The institute conducts research into ocean pollution, flame retardants, microplastics and plastic pollution, sentinel species and climate change.
Diana S. Aga is a Filipino-American chemist who is the Henry M. Woodburn Chair at the University at Buffalo. She was awarded the 2017 American Chemical Society Schoellkopf Medal in recognition of her work in environmental chemistry. The Schoellkopf Medal is a local section award of the American Chemical Society. Over the years, numerous University at Buffalo faculty have received this recognition.
Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).