Octabromodiphenyl ether

Octabromodiphenyl ether

General chemical structure of octabromodiphenyl ethers, where m + n = 8
Names
Other names Octabromobiphenyl ether; OctaBDE, Octa-BDE; Octabromodiphenyl oxide; OBDPO
Identifiers
CAS Number	32536-52-0^Y
ChemSpider	None
ECHA InfoCard	100.046.428
EC Number	251-087-9
UNII	QFL9YO91JE^Y
CompTox Dashboard (EPA)	DTXSID8024236
Properties
Chemical formula	C12H2Br8O
Molar mass	801.379 g·mol^−1
Appearance	White solid[1]
Density	2.9 g/cm^3[1]
Melting point	Depends on product composition[1]
Boiling point	Decomposes[1]
Solubility in water	< 0.1 mg/L[1]
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H360Df
Related compounds
Related polybrominated diphenyl ethers	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). N verify (what is ^YN ?) Infobox references

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).

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]

Structure	Congener	Name	Fraction
	BDE-153	2,2′,4,4′,5,5′-hexa- bromodiphenyl ether	0.15–8.7%
	BDE-154	2,2′,4,4′,5,6′-hexa- bromodiphenyl ether	0.04–1.1%
	BDE-171	2,2′,3,3′,4,4′,6-hepta- bromodiphenyl ether	0.17–1.8%
	BDE-180	2,2′,3,4,4′,5,5′-hepta- bromodiphenyl ether	n.d.–1.7%
	BDE-183	2,2′,3,4,4′,5′,6-hepta- bromodiphenyl ether	13–42%
	BDE-196	2,2′,3,3′,4,4′,5,6′-octa- bromodiphenyl ether	3.1–10.5%
	BDE-197	2,2′,3,3′,4,4′,6,6′-octa- bromodiphenyl ether	11–22%
	BDE-203	2,2′,3,4,4′,5,5′,6-octa- bromodiphenyl ether	4.4–8.1%
	BDE-206	2,2′,3,3′,4,4′,5,5′,6-nona- bromodiphenyl ether	1.4–7.7%
	BDE-207	2,2′,3,3′,4,4′,5,6,6′-nona- bromodiphenyl ether	11–12%
	BDE-209	Deca- 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]

References

1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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. 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. 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. 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.