Octabromodiphenyl ether

Last updated
Octabromodiphenyl ether
Polybrominated diphenyl ether.svg
General chemical structure of octabromodiphenyl ethers, where m + n = 8
Names
Other names
Octabromobiphenyl ether; OctaBDE, Octa-BDE; Octabromodiphenyl oxide; OBDPO
Identifiers
ChemSpider
  • None
ECHA InfoCard 100.046.428 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 251-087-9
UNII
Properties
C12H2Br8O
Molar mass 801.379 g·mol−1
AppearanceWhite solid [1]
Density 2.9 g/cm3 [1]
Melting point Depends on product composition [1]
Boiling point Decomposes [1]
< 0.1 mg/L [1]
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg
Danger
H360Df
Related compounds
Decabromodiphenyl ether, Pentabromodiphenyl ether
Related compounds
diphenyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Octabromodiphenyl ether (octaBDE, octa-BDE, OBDE, octa, octabromodiphenyl oxide, OBDPO) is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs).

Contents

Composition, uses, and production

Commercial octaBDE (also known as "Octabrom") is a technical mixture of different PBDE congeners having an average of 7.2 to 7.7 bromine atoms per molecule of diphenyl ether. [2] The predominant congeners in commercial octaBDE are those of heptabromodiphenyl ether and octaBDE. [2] [3] The term octaBDE alone refers to isomers of octabromodiphenyl ether (PBDE congener numbers 194–205). [4]

Composition of commercial octaBDE [5]
StructureCongenerNameFraction
BDE-153.svg BDE-1532,2′,4,4′,5,5′-hexa-
bromodiphenyl ether
0.15–8.7%
BDE-154.svg BDE-1542,2′,4,4′,5,6′-hexa-
bromodiphenyl ether
0.04–1.1%
BDE-171.svg BDE-1712,2′,3,3′,4,4′,6-hepta-
bromodiphenyl ether
0.17–1.8%
BDE-180.svg BDE-1802,2′,3,4,4′,5,5′-hepta-
bromodiphenyl ether
n.d.–1.7%
BDE-183.svg BDE-1832,2′,3,4,4′,5′,6-hepta-
bromodiphenyl ether
13–42%
BDE-196.svg BDE-1962,2′,3,3′,4,4′,5,6′-octa-
bromodiphenyl ether
3.1–10.5%
BDE-197.svg BDE-1972,2′,3,3′,4,4′,6,6′-octa-
bromodiphenyl ether
11–22%
BDE-203.svg BDE-2032,2′,3,4,4′,5,5′,6-octa-
bromodiphenyl ether
4.4–8.1%
BDE-206.svg BDE-2062,2′,3,3′,4,4′,5,5′,6-nona-
bromodiphenyl ether
1.4–7.7%
BDE-207.svg BDE-2072,2′,3,3′,4,4′,5,6,6′-nona-
bromodiphenyl ether
11–12%
BDE-209.svg BDE-209Deca-
bromodiphenyl ether
1.3–50%

Only congeners with more than 1% listed.

OctaBDE is used in conjunction with antimony trioxide as a flame retardant in the housings of electrical and electronic equipment, mainly in the plastic acrylonitrile butadiene styrene, but also in high impact polystyrene, polybutylene terephthalate and polyamides. [6] Typically 12–15% of the weight of the final product will consist of octaBDE. [6]

The annual demand worldwide was estimated as 3,790 tonnes in 2001, of which Asia accounted for 1,500 tonnes, the Americas 1,500 tonnes, and Europe 610 tonnes. [7] The United Nations Environment Programme reports "Since 2004, it [octaBDE] is no longer produced in the EU, USA and the Pacific Rim and there is no information that indicates it is being produced in developing countries." [3]

Environmental chemistry

OctaBDE is released by different processes into the environment, such as emissions from the manufacture of octaBDE-containing products and from the products themselves. [3] Elevated concentrations can be found in air, water, soil, food, sediment, sludge, and dust. [3] [8] [9]

In the environment, "photolysis, anaerobic degradation and metabolism in biota" can cause debromination of octaBDE, which produces PBDEs with fewer bromine atoms "which may have higher toxicity and bioaccumulation potential." [3]

Exposures and health effects

OctaBDE may enter the body by ingestion or inhalation. [4] It is "stored mainly in body fat" and may stay in the body for years. [4] In an investigation carried out by the WWF, "the brominated flame retardant chemical (PBDE 153), which is a component of the penta- and octa- brominated diphenyl ether flame retardant products" was found in all blood samples of 14 ministers of health and environment of 13 European Union countries. [10]

The chemical has no proven health effects in humans; however, based on animal experiments, octaBDE may have effects on "the liver, thyroid, and neurobehavioral development." [4]

Governmental actions

The European Union has carried out a comprehensive risk assessment under the Existing Substances Regulation 793/93/EEC. [6] As a consequence, the EU has banned the use of octaBDE since 2004. [11]

In the United States, as of 2005, "no new manufacture or import of" pentaBDE and octaBDE "can occur... without first being subject to EPA [i.e., United States Environmental Protection Agency ] evaluation." [12] As of mid-2007, a total of eleven states in the U.S. had banned octaBDE. [13]

In May 2009, commercial octaBDE was added to the Stockholm Convention as it meets the criteria for the so-called persistent organic pollutants of persistence, bioaccumulation and toxicity.

Alternatives

Alternatives to octaBDE include tetrabromobisphenol A, 1,2-bis (pentabromophenoxy) ethane, 1,2-bis(tribromophenoxy)ethane, triphenyl phosphate, resorcinol bis(diphenylphosphate), and brominated polystyrene; however, for each of these "the existing data on toxicological and ecotoxicological effects are fewer than for octabromodiphenyl ether." [14]

Related Research Articles

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 life-saving benefits of fire retardants led to their popularization. Standards for mass transit vehicles continues to increase as of 2021.

<span class="mw-page-title-main">Flame retardant</span> Substance applied to items to slow burning or delay ignition

Flame retardants are 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 prevent or slow the further development of flames by a variety of different physical and chemical mechanisms. 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.

<span class="mw-page-title-main">Endocrine disruptor</span> Chemicals that can interfere with endocrine or hormonal systems

Endocrine disruptors, sometimes also referred to as hormonally active agents, endocrine disrupting chemicals, or endocrine disrupting compounds are chemicals that can interfere with endocrine systems. These disruptions can cause numerous adverse human health outcomes, including alterations in sperm quality and fertility; abnormalities in sex organs‚ endometriosis‚ early puberty‚ altered nervous system or immune function; certain cancers; respiratory problems; metabolic issues; diabetes, obesity, or cardiovascular problems; growth, neurological and learning disabilities, and more. Found in many household and industrial products, endocrine disruptors "interfere with the synthesis, secretion, transport, binding, action, or elimination of natural hormones in the body that are responsible for development, behavior, fertility, and maintenance of homeostasis ."

<span class="mw-page-title-main">Organophosphate</span> Organic compounds with the structure O=P(OR)3

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. Organophosphates are best known for their use as pesticides.

<span class="mw-page-title-main">Persistent organic pollutant</span> Organic compounds that are resistant to environmental degradation

Persistent organic pollutants (POPs) are organic compounds that are resistant to degradation through chemical, biological, and photolytic processes. They are toxic and 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.

A bromide ion is the negatively charged form (Br) of the element bromine, a member of the halogens group on the periodic table. Most bromides are colorless. Bromides have many practical roles, being found in anticonvulsants, flame-retardant materials, and cell stains. Although uncommon, chronic toxicity from bromide can result in bromism, a syndrome with multiple neurological symptoms. Bromide toxicity can also cause a type of skin eruption, see potassium bromide. The bromide ion has an ionic radius of 196 pm.

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.

<span class="mw-page-title-main">Fire retardant</span> Substance reducing flammability

A fire retardant is a substance that is used to slow down or stop the spread of fire or reduce its intensity. This is commonly accomplished by chemical reactions that reduce the flammability of fuels or delay their combustion. Fire retardants may also cool the fuel through physical action or endothermic chemical reactions. Fire retardants are available as powder, to be mixed with water, as fire-fighting foams and fire-retardant gels. Fire retardants are also available as coatings or sprays to be applied to an object.

<span class="mw-page-title-main">Hexabromocyclododecane</span> Chemical compound

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 used as thermal insulation in construction. 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.

<span class="mw-page-title-main">Decabromodiphenyl ether</span> Chemical compound

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).

<span class="mw-page-title-main">Tetrabromobisphenol A</span> Chemical compound

Tetrabromobisphenol A (TBBPA) is a brominated flame retardant. The compound is a white solid, although commercial samples appear yellow. It is one of the most common flame retardants.

<span class="mw-page-title-main">Triphenyl phosphate</span> Chemical compound

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.

<span class="mw-page-title-main">Diphenyl ether</span> Chemical compound

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.

Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.

<span class="mw-page-title-main">Congener (chemistry)</span> Related substances

In chemistry, congeners are chemical substances "related to each other by origin, structure, or function".

<span class="mw-page-title-main">Susan Shaw (conservationist)</span> American scientist, explorer, conservationist, author (1943–2022)

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.

<span class="mw-page-title-main">Decabromodiphenyl ethane</span> Chemical compound

Decabromodiphenyl ethane is a chemical compound used as a brominated flame retardant. It was commercialised in the 1990s as an alternative for decabromodiphenyl ether, 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.

<span class="mw-page-title-main">Bis(2-ethylhexyl)tetrabromophthalate</span> Chemical compound

Bis(2-ethylhexyl)tetrabromophthalate (or TBPH), is a brominated phthalate derivative with the formula C24H34Br4O4 commonly used as a brominated flame retardant (BFR).

References

  1. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 United States Patent and Trademark Office. Melting point enhancement of partially brominated diphenyl oxide mixtures. US Patent 5,000,879 issued on March 19, 1991.
  3. 1 2 3 4 5 Ad hoc working group on C-Octabromodiphenyl ether under the Persistent Organic Pollutants Review Committee of the Stockholm Convention. Draft risk profile: commercial octabromodiphenyl ether. United Nations Environment Programme, August 2007.
  4. 1 2 3 4 Agency for Toxic Substances and Disease Registry. Toxicological Profile for Polybrominated Biphenyls and Polybrominated Diphenyl Ethers (PBBs and PBDEs). Atlanta, GA: U.S. Department of Health and Human Services, Public Health Service, September 2004.
  5. M. J. La Guardia, R. C. Hale, E. Harvey: Detailed Polybrominated Diphenyl Ether (PBDE) Congener Composition of the Widely Used Penta-, Octa-, and Deca-PBDE Technical Flame-retardant Mixtures, Environ. Sci. Technol., 2006, 40, 6247–6254, doi : 10.1021/es060630m.
  6. 1 2 3 European Union risk assessment report. Diphenyl ether, octabromo derivative. Luxembourg: Office for Official Publications of the European Communities, 2003. Publication EUR 20403 EN.
  7. Bromine Science and Environmental Forum. Major Brominated Flame Retardants Volume Estimates: Total Market Demand By Region in 2001. Archived 2006-11-30 at the Wayback Machine 21 January 2003.
  8. Hale RC, La Guardia MJ, Harvey E, Gaylor MO, Mainor TM (2006): Brominated flame retardant concentrations and trends in abiotic media. Chemosphere. 64(2):181-6. doi : 10.1016/j.chemosphere.2005.12.006 PMID   16434082
  9. Stapleton, Heather M., et al. Polybrominated Diphenyl Ethers in House Dust and Clothes Dryer Lint. Environmental Science & Technology 39(4), 925-931, 2005. doi : 10.1021/es0486824
  10. WWF Detox Campaign. Bad Blood? A Survey of Chemicals in the Blood of European Ministers. October 2004.
  11. Directive 2003/11/Ec of the European Parliament and of the Council of 6 February 2003 amending for the 24th time Council Directive 76/769/EEC relating to restrictions on the marketing and use of certain dangerous substances and preparations (pentabromodiphenyl ether, octabromodiphenyl ether). Official Journal of the European Union 15.2.2003.
  12. U.S. Environmental Protection Agency. Polybrominated diphenylethers (PBDEs). "Last updated on Thursday, August 2nd, 2007." Accessed 2007-10-26.
  13. Maine Joins Washington, Bans PBDEs. Archived 2007-08-02 at the Wayback Machine Washington, DC: National Caucus of Environmental Legislators, June 18, 2007.
  14. Risk & Policy Analysts Limited. Octabromodiphenyl Ether. Risk Reduction Strategy and Analysis of Advantages and Drawbacks. Final Report. Prepared for Department for Environment, Food and Rural Affairs, United Kingdom, June 2002.