Pentabromodiphenyl ether

Last updated
Pentabromodiphenyl ether
Polybrominated diphenyl ether.svg
General chemical structure of pentabromodiphenyl ethers, where n + m = 5
Names
Other names
PentaBDE; Penta-BDE; PeBDE; Penta; PBDPO; Pentabromobiphenyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.425 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 251-084-2
KEGG
PubChem CID
RTECS number
  • DD6625350
UNII
UN number 3152 3077
  • 2,2',4,4',5:InChI=1S/C12H5Br5O/c13-6-1-2-11(9(16)3-6)18-12-5-8(15)7(14)4-10(12)17/h1-5H
    Key: WHPVYXDFIXRKLN-UHFFFAOYSA-N
  • 2,2′,4,4′,6:InChI=1S/C12H5Br5O/c13-6-1-2-11(8(15)3-6)18-12-9(16)4-7(14)5-10(12)17/h1-5H
    Key: NSKIRYMHNFTRLR-UHFFFAOYSA-N
  • 2,2',4,4',5:C1=CC(=C(C=C1Br)Br)OC2=CC(=C(C=C2Br)Br)Br
  • 2,2′,4,4′,6:C1=CC(=C(C=C1Br)Br)OC2=C(C=C(C=C2Br)Br)Br
Properties
C12H5Br5O
Molar mass 564.691 g·mol−1
AppearanceViscous white to amber-colored liquid [1]
Density 2.25-2.28 g/cm3 [1]
Melting point −7 to 3 °C (19 to 37 °F; 266 to 276 K)
Boiling point Decomposes [1]
not soluble
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Warning
H362, H373, H410
Lethal dose or concentration (LD, LC):
5000 mg/kg (oral, rat) [1]
Related compounds
octabromodiphenyl ether, decabromodiphenyl ether
Related compounds
diphenylether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Pentabromodiphenyl ether (also known as pentabromodiphenyl oxide) 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).

Contents

Composition, uses, and production

Commercial pentaBDE is a technical mixture of different PBDE congeners, with BDE-47 (2,2',4,4'- tetrabromodiphenyl ether) and BDE-99 (2,2',4,4',5-pentabromodiphenyl ether) as the most abundant. [2] The term pentaBDE alone refers to isomers of pentabromodiphenyl ether (PBDE congener numbers 82-127). [3]

Composition of commercial pentaBDE [4]
StructureCongenerNameFraction
BDE-47.svg BDE-472,2′,4,4′-tetra-
bromodiphenyl ether
38–42%
BDE-85.svg BDE-852,2′,3,4,4′-penta-
bromodiphenyl ether
2.2–3.0 %
BDE-99.svg BDE-992,2′,4,4′,5-penta-
bromodiphenyl ether
45–49%
BDE-100.svg BDE-1002,2′,4,4′,6-penta-
bromodiphenyl ether
7.8–13 %
BDE-153.svg BDE-1532,2′,4,4′,5,5′-hexa-
bromodiphenyl ether
5.3–5.4 %
BDE-154.svg BDE-1542,2′,4,4′,5,6′-hexa-
bromodiphenyl ether
2.7–4.5 %

Only congeners with more than 1% listed.

Commercial pentaBDE is most commonly used as a flame retardant in flexible polyurethane foam; it was also used in printed circuit boards in Asia, and in other applications. [2] The annual demand worldwide was estimated as 7,500 tonnes in 2001, of which the Americas accounted for 7,100 tonnes, Europe 150 tonnes, and Asia 150 tonnes. [5] The global industrial demand increased from 4,000 tonnes annually in 1991 to 8,500 tonnes annually in 1999. [6] As of 2007, "there should be no current production of C-PentaBDE [commercial pentaBDE] in Europe, Japan, Canada, Australia and the US"; however, it is possible that production continues elsewhere in the world. [2]

Environmental chemistry

PentaBDE is released by different processes into the environment, such as emissions from manufacture of pentaBDE-containing products and from the products themselves. [2] Elevated concentrations can be found in air, water, soil, food, sediment, sludge, and dust. [2] [7] [8]

Exposures and health effects

PentaBDE may enter the body by ingestion or inhalation. [3] It is "stored mainly in body fat" and may stay in the body for years. [3] A 2007 study found that PBDE 47 (a tetraBDE) and PBDE 99 (a pentaBDE) had biomagnification factors in terrestrial carnivores and humans of 98, higher than any other industrial chemicals studied. [9] 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, pentaBDE may have effects on "the liver, thyroid, and neurobehavioral development." [3]

Voluntary and governmental actions

In Germany, industrial users of pentaBDE "agreed to a voluntary phaseout in 1986." [11] In Sweden, the government "phase[d] out the production and use of the [pentaBDE] compounds by 1999 and a total ban on imports came into effect within just a few years." [11] The European Union (EU) has carried out a comprehensive risk assessment under the Existing Substances Regulation 793/93/EEC; [12] as a consequence, the EU has banned the use of pentaBDE since 2004. [13]

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." [14] As of mid-2007, a total of eleven states in the U.S. had banned pentaBDE. [15]

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

Alternatives

The EPA organized a Furniture Flame Retardancy Partnership beginning in 2003 "to better understand fire safety options for the furniture industry" after pentaBDE "was voluntarily phased out of production by the sole U.S. manufacturer on December 31, 2004." [16] In 2005 the Partnership published evaluations of alternatives to pentaBDE, including triphenyl phosphate, tribromoneopentyl alcohol, tris(1,3-dicholoro-2-propyl)phosphate, and 12 proprietary chemicals. [17]

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 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).

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

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.

<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 cancerous tumors, birth defects, and other developmental disorders. 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">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 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.

<span class="mw-page-title-main">Polybrominated biphenyl</span> Group of chemical compounds

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.

<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 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.

<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.

Octabromodiphenyl ether is a brominated flame retardant which belongs to the group of polybrominated diphenyl ethers (PBDEs).

<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.

Persistent, bioaccumulative and toxic substances (PBTs) are a class of compounds that have high resistance to degradation from abiotic and biotic factors, high mobility in the environment and high toxicity. Because of these factors PBTs have been observed to have a high order of bioaccumulation and biomagnification, very long retention times in various media, and widespread distribution across the globe. Most PBTs in the environment are either created through industry or are unintentional byproducts.

<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.

Environmental issues in Toronto encompasses all those concerns and opportunities presented by the environment of Toronto. Many are harmful effects, such as the pollution of air and water, while others are factors influenced by urban infrastructures such as highways and public transportation services. As a result of the city's large population, substantial waste is produced annually.

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 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 4 5 Persistent Organic Pollutants Review Committee of the Stockholm Convention. Commercial Pentabromodiphenyl Ether: Risk Management Evaluation. United Nations Environment Programme, August 2007.
  3. 1 2 3 4 Agency for Toxic Substances and Disease Registry. Toxicological Profile for Polybrominated Biphenyls and Polybrominated Diphenyl Ethers (PBBs and PBDEs). Archived 2007-10-31 at the Wayback Machine Atlanta, GA: U.S. Department of Health and Human Services, Public Health Service, September 2004.
  4. 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.
  5. 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.
  6. Dynamic Substance Flow Analysis Model for Selected Brominated Flame Retardants as a Base for Decision Making on Risk Reduction Measures, study for the Swiss National Science Foundation, 2007, page 23
  7. 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
  8. Stapleton, Heather M., et al. Polybrominated Diphenyl Ethers in House Dust and Clothes Dryer Lint. Environmental Science & Technology 39(4), 925-931, 2005.
  9. Kelly, Barry C., et al. Food Web–Specific Biomagnification of Persistent Organic Pollutants. Science 13 July 2007: Vol. 317. no. 5835, pp.236-239.
  10. WWF Detox Campaign. Bad Blood? A Survey of Chemicals in the Blood of European Ministers. October 2004.
  11. 1 2 Alcock, R. E. and J. Busby (2006): Risk migration and scientific advance: The case of flame-retardant compounds. Risk Analysis 26(2): 369-381. doi : 10.1111/j.1539-6924.2006.00739.x PMID   16573627
  12. European Union risk assessment report. Diphenyl ether, pentabromo derivative (pentabromodiphenyl ether). Archived 2007-03-17 at the Wayback Machine Luxembourg: Office for Official Publications of the European Communities, 2001. Publication EUR 19730 EN. ISBN   92-894-0479-5
  13. 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.
  14. U.S. Environmental Protection Agency. Polybrominated diphenylethers (PBDEs). "Last updated on Thursday, August 2nd, 2007." Accessed 2007-10-26.
  15. Maine Joins Washington, Bans PBDEs. Archived 2007-08-02 at the Wayback Machine Washington, DC: National Caucus of Environmental Legislators, June 18, 2007.
  16. EPA. Furniture Flame Retardancy Partnership page. "Last updated on Monday, September 18th, 2006." Accessed 2007-10-31.
  17. EPA. Environmental Profiles of Chemical Flame-Retardant Alternatives for Low-Density Polyurethane Foam. Volumes 1 and 2. September 2005.