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| ImageSize1 = 230
| ImageAlt1 = Ball-and-stick model of the decabromodiphenyl ether molecule
|
| OtherNames = {{bulleted list|2,3,4,5,6-Pentabromo-1-(2,3,4,5,6-pentabromophenoxy)benzene|6,6′-Oxybis(1,2,3,4,5-pentabromobenzene)|decabromodiphenyl oxide (DBDPO)| bis(pentabromophenyl) ether }}
|Section1={{Chembox Identifiers
| Abbreviations =
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| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1163-19-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = N80BQ29A0H
| EC_number = 214-604-9
| PubChem = 14410
| SMILES = Brc2c(Oc1c(Br)c(Br)c(Br)c(Br)c1Br)c(Br)c(Br)c(Br)c2Br
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| MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 82436
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19383
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| Density = 3.364 g/cm<sup>3</sup> solid
| MeltingPtC = 294 to 296
|
| BoilingPtC = 425
| BoilingPt_notes = (decomposition)<ref name=GESTIS/>
| Solubility = 20-30
| SolubleOther =
| Solvent =
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|Section7={{Chembox Hazards
| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=194425&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F194425%3Flang%3Den]
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
▲| MainHazards = Xn <ref name="GESTIS">{{GESTIS|ZVG=493931|CAS=1163-19-5|Name=Decabromodiphenyl ether|Date=17 June 2008}}</ref>
| HPhrases = {{H-phrases|302|312|319|332|341|373|413}}
| PPhrases = {{P-phrases|201|202|260|261|264|270|271|273|280|281|301+312|302+352|304+312|304+340|305+351+338|308+313|312|314|322|330|337+313|363|405|501}}
| NFPA-H = 2
| NFPA-F = 0
| NFPA-R = 0
| NFPA-S =
| FlashPtC = 241
| AutoignitionPtC =
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| OtherCompounds = [[Diphenyl ether]]}}
}}
'''Decabromodiphenyl ether''' (also referred to as '''decaBDE''', '''DBDE''', '''BDE-209''') is a [[brominated flame retardant]] which belongs to the group of [[polybrominated diphenyl ether]]s (PBDEs). It was commercialised in the 1970s and was initially thought to be safe,<ref>{{cite journal |last1=Liepins |first1=R |last2=Pearce |first2=E M |title=Chemistry and toxicity of flame retardants for plastics. |journal=Environmental Health Perspectives |date=October 1976 |volume=17 |pages=55–63 |doi=10.1289/ehp.761755|pmid=1026419 |pmc=1475265 }}</ref><ref>{{cite journal |last1=Norris |first1=J M |last2=Kociba |first2=R J |last3=Schwetz |first3=B A |last4=Rose |first4=J Q |last5=Humiston |first5=C G |last6=Jewett |first6=G L |last7=Gehring |first7=P J |last8=Mailhes |first8=J B |title=Toxicology of octabromobiphenyl and decabromodiphenyl oxide. |journal=Environmental Health Perspectives |date=June 1975 |volume=11 |pages=153–161 |doi=10.1289/ehp.7511153|pmid=126149 |pmc=1475203 }}</ref> 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,<ref>{{cite web |title=c-decaBDE |url=http://chm.pops.int/Implementation/Alternatives/AlternativestoPOPs/ChemicalslistedinAnnexA/cdecaBDE/tabid/5985/Default.aspx |website=chm.pops.int |publisher=Secretariat of the Stockholm Convention |access-date=8 January 2023}}</ref><ref name="COP2017">[https://treaties.un.org/doc/Publication/CN/2017/CN.766.2017-Eng.pdf Reference: C.N.766.2017.TREATIES-XXVII.15 (Depositary Notification)]</ref> 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.
==Composition, uses, and production==
'''Commercial decaBDE''' is a technical mixture of
DecaBDE is a [[flame retardant]]. The chemical "is always used in conjunction with [[antimony trioxide]]" in [[polymer]]s, mainly in "high impact polystyrene (HIPS) which is used in the television industry for cabinet backs."<ref name="JRC" /> DecaBDE is also used for "polypropylene drapery and upholstery fabric" by means of backcoating and "may also be used in some synthetic carpets."<ref name="JRC" />
The annual demand worldwide was estimated as 56,100 [[tonnes]] in 2001, of which the Americas accounted for 24,500 tonnes, Asia 23,000 tonnes, and Europe 7,600 tonnes.<ref name="JRC" /> In 2012 between 2500 and 5000 metric tonnes of Deca-BDE was sold in Europe.<ref>{{Cite web | url=http://www.vecap.info/index.php?mact=NewsPublications,cntnt01,details,0&cntnt01documentid=20&cntnt01returnid=57 | title=VECAP - Annual Progress Report}}</ref> As of 2007, [[Albemarle Corporation|Albemarle]] in the U.S., [[Chemtura]] in the U.S., ICL-IP in Israel, and Tosoh Corporation in Japan are the main manufacturers of DecaBDE.<ref name=Maine2007>[http://www.maine.gov/dep/rwm/publications/legislativereports/pdf/finalrptjan07.pdf Brominated Flame Retardants: Third annual report to the Maine Legislature.] {{webarchive|url=https://web.archive.org/web/20070311231314/http://www.maine.gov/dep/rwm/publications/legislativereports/pdf/finalrptjan07.pdf |date=2007-03-11 }} Augusta, Maine: Maine Department of Environmental Protection and Maine Center for Disease Control & Prevention, January 2007.</ref>
Despite its listing in Annex A to the [[Stockholm Convention]], decaBDE is still produced in China, namely in the provinces [[Shandong]] and [[Jiangsu]].<ref>{{Cite journal|date=2020-05-01|title=Trends of production, consumption and environmental emissions of Decabromodiphenyl ether in mainland China|url=https://www.sciencedirect.com/science/article/abs/pii/S0269749119354946|journal=Environmental Pollution|language=en|volume=260|pages=114022|doi=10.1016/j.envpol.2020.114022|issn=0269-7491|last1=Chen |first1=Yuan |last2=Li |first2=Jinhui |last3=Tan |first3=Quanyin |pmid=31995770 |s2cid=210951187 }}</ref><ref>{{Cite journal|last1=Zhen|first1=Xiaomei|last2=Li|first2=Yanfang|last3=Tang|first3=Jianhui|last4=Wang|first4=Xinming|last5=Liu|first5=Lin|last6=Zhong|first6=Mingyu|last7=Tian|first7=Chongguo|date=2021-05-17|title=Decabromodiphenyl Ether versus Decabromodiphenyl Ethane: Source, Fate, and Influencing Factors in a Coastal Sea Nearing Source Region|url=https://doi.org/10.1021/acs.est.0c08528|journal=Environmental Science & Technology|volume=55 |issue=11 |pages=7376–7385 |doi=10.1021/acs.est.0c08528|pmid=33998794 |bibcode=2021EnST...55.7376Z |s2cid=234747918 |issn=0013-936X}}</ref>
==Environmental chemistry==
As stated in a 2006 review, "Deca-BDE has long been characterized as an environmentally stable and inert product that was not capable of degradation in the environment, not toxic, and therefore of no concern."<ref name=Alcock2006>{{cite journal |vauthors=Alcock RE, Busby J |title=Risk migration and scientific advance: the case of flame-retardant compounds |journal=Risk Anal. |volume=26 |issue=2 |pages=369–81 |date=April 2006 |pmid=16573627 |doi=10.1111/j.1539-6924.2006.00739.x |s2cid=37119476 }}</ref> However, "some scientists had not particularly believed that Deca-BDE was so benign, particularly as evidence to this effect came largely from the industry itself."<ref name=Alcock2006/> One problem in studying the chemical was that "the detection of Deca-BDE in environmental samples is difficult and problematic"; only in the late 1990s did "analytical advances... allow
DecaBDE is released by
===The question of debromination===
An important scientific issue is whether decaBDE debrominates in the environment to PBDE congeners with fewer bromine atoms, since such PBDE congeners may be more toxic than decaBDE itself.<ref name=ATSDR2004/> Debromination may be "biotic" (caused by biological means) or "abiotic" (caused by nonbiological means).<ref name=Maine2007/> The [[European Union]] (EU) in May 2004 stated "the formation of PBT/vPvB ([[Persistent, bioaccumulative and toxic substances|Persistent, Bioaccumulative, and Toxic]] / very Persistent, very Bioaccumulative
In May 2006, the EPHA Environment Network (now The Health and Environment Alliance) released a report reviewing the available scientific literature<ref name=Stapleton2006May>Stapleton, Heather M. [http://www.env-health.org/IMG/pdf/Debromination_paper_04052006_2_.pdf Brominated Flame Retardants: Assessing DecaBDE Debromination in the Environment.] Brussels, Belgium: EPHA Environment Network, May 2006.</ref> and concluding the following:
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* "Some fish appear capable of debrominating BDE 209 through metabolism. The extent of the metabolism varies among fish and it is difficult to determine the extent of debromination that would occur in the wild."
Subsequently, many studies have been published concerning decaBDE debromination. Common [[Anaerobic organism|anaerobic]] soil bacteria debrominated decaBDE and octaBDE in a 2006 study.<ref name=He2007>{{cite journal |vauthors=He J, Robrock KR, Alvarez-Cohen L |title=Microbial reductive debromination of polybrominated diphenyl ethers (PBDEs) |journal=Environ. Sci. Technol. |volume=40 |issue=14 |pages=4429–34 |date=July 2006 |pmid=16903281 |doi= 10.1021/es052508d|bibcode=2006EnST...40.4429H |url=http://pubs.acs.org/cgi-bin/abstract.cgi/esthag/2006/40/i14/abs/es052508d.html}}</ref> In 2006-2007 studies, metabolic debromination of decaBDE was demonstrated in fish,<ref name=Stapleton2006Aug>{{cite journal |author=Stapleton HM |title=In vivo and in vitro debromination of decabromodiphenyl ether (BDE 209) by juvenile rainbow trout and common carp |journal=Environ. Sci. Technol. |volume=40 |issue=15 |pages=4653–8 |date=August 2006 |pmid=16913120 |url=http://pubs.acs.org/cgi-bin/abstract.cgi/esthag/2006/40/i15/abs/es060573x.html |doi=10.1021/es060573x |name-list-
In March 2007 the Illinois Environmental Protection Agency concluded "it can be questioned how much abiotic and microbial degradation [of decaBDE] occurs under normal environmental conditions, and it is not clear whether the more toxic lower-brominated PBDEs are produced in significant quantities by any of these pathways."<ref name=IL2007>Illinois Environmental Protection Agency. [http://www.epa.state.il.us/reports/decabde-study/index.html Report on Alternatives to the Flame Retardant DecaBDE: Evaluation of Toxicity, Availability, Affordability, and Fire Safety Issues.] March 2007.</ref> In September 2010, the UK Advisory Committee on Hazardous Substances issued an opinion that ‘there is strong but incomplete, scientific evidence indicating that Deca-BDE has the potential to undergo transformation to lower brominated congeners in the environment'.<ref>Advisory Committee on Hazardous Substances. ACHS opinion on the Draft Environmental Risk Assessment Report for Decabromodiphenyl ether (DecaBDE) (CAS 1163 19 5). Department for Environment, Food and Rural Affairs [https://web.archive.org/web/20110704155154/http://archive.defra.gov.uk/environment/quality/chemicals/achs/documents/achs-decaBDE-opinion-100923.pdf
==Pharmacokinetics==
Exposure to decaBDE is thought to occur by means of ingestion.<ref name=ATSDR2004/> Humans and animals do not absorb decaBDE well; at most, perhaps 2% of an oral dose is absorbed.<ref name=BFRIP2002>[http://www.tera.org/peer/VCCEP/DECA/DBDPO%20Assessment.pdf Voluntary Children’s Chemical Evaluation Program (VCCEP) Data Summary: Decabromodiphenyl Ether (a.k.a. Decabromodiphenyl Oxide, DBDPO) CAS # 1163-19-5.] {{webarchive|url=https://web.archive.org/web/20050220175325/http://www.tera.org/peer/VCCEP/DECA/DBDPO%20Assessment.pdf |date=2005-02-20 }} American Chemistry Council’s Brominated Flame Retardant Industry Panel (BFRIP), December 17, 2002.</ref><ref name=BFRIP2003>[http://www.tera.org/peer/VCCEP/DECA/VCCEP%20DBDPO.pdf Report of the Peer Consultation Meeting On Decabromodiphenyl Ether.] {{webarchive|url=https://web.archive.org/web/20060927195453/http://www.tera.org/peer/VCCEP/DECA/VCCEP%20DBDPO.pdf |date=2006-09-27 }} American Chemistry Council’s Brominated Flame Retardant Industry Panel for the Voluntary Children's Chemical Evaluation Program (VCCEP), September 30, 2003.</ref> It is believed that "the small amount of decaBDE that is absorbed can be metabolized".<ref name=ATSDR2004/>
Once in the body, decaBDE "might leave unchanged or as metabolites, mainly in the feces and in very small amounts in the urine, within a few days," in contrast with "lower brominated PBDEs... [which] might stay in your body for many years, stored mainly in body fat."<ref name=ATSDR2004/> In workers with occupational exposure to PBDEs, the calculated apparent half-life for decaBDE was 15 days, as opposed to (for example) an octaBDE congener with a half-life of 91 days.<ref name=Thuresson2006>{{cite journal|vauthors=Thuresson K, Höglund P, Hagmar L, Sjödin A, Bergman A, Jakobsson K |title=Apparent Half-Lives of Hepta- to Decabrominated Diphenyl Ethers in Human Serum as Determined in Occupationally Exposed Workers |journal=Environ. Health Perspect. |volume=114 |issue=2 |pages=176–81 |date=February 2006 |pmid=16451851 |pmc=1367828
===Detection in humans===
In the general population, decaBDE has been found in blood and breast milk, but at lower levels than other PBDE congeners such as 47, 99, and 153.<ref name=Lorber2007>{{cite journal |author=Lorber M |title=Exposure of Americans to polybrominated diphenyl ethers |journal=J Expo Sci Environ Epidemiol |volume=18 |issue=1 |pages=2–19 |date=January 2008 |pmid=17426733 |doi=10.1038/sj.jes.7500572 |doi-access=free }}</ref> An investigation carried out by the [[World Wide Fund for Nature|WWF]] detected decaBDE in blood samples from 3 of 14 ministers of health and environment of European Union countries, while (for example) PBDE-153 was found in all 14.<ref>WWF Detox Campaign. [http://assets.panda.org/downloads/badbloodoctober2004.pdf Bad Blood? A Survey of Chemicals in the Blood of European Ministers.] October 2004.</ref>
==Possible health effects in humans==
In 2004, ATSDR wrote "Nothing definite is known about the health effects of PBDEs in people. Practically all of the available information is from studies of laboratory animals. Animal studies indicate that commercial decaBDE mixtures are generally much less toxic than the products containing lower brominated PBDEs.
===Liver===
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===Thyroid===
One 2006 review concluded "Decreases in thyroid hormone levels have been reported in several studies, and thyroid gland enlargement (an early sign of hypothyroidism) has been shown in studies of longer duration exposure."<ref name=IL2006/> A 2007 experiment giving decaBDE to pregnant mice found that decaBDE "is likely an endocrine disrupter in male mice following exposure during development" based on results such as decreased serum [[triiodothyronine]].<ref name=Tseng2007>{{cite journal |author=Tseng LH |title=Developmental exposure to decabromodiphenyl ether (PBDE 209): effects on thyroid hormone and hepatic enzyme activity in male mouse offspring |journal=Chemosphere |volume=70 |issue=4 |pages=640–7 |date=January 2008 |pmid=17698168 |doi=10.1016/j.chemosphere.2007.06.078 |name-list-
===Reproductive/developmental effects===
"Significant data gaps" exist in the scientific literature on a possible relationship between decaBDE and reproductive/developmental effects.<ref name=IL2006/> A 2006 study of mice found that decaBDE decreased some "sperm functions."<ref name=Tseng2006>{{cite journal |author=Tseng LH |title=Postnatal exposure of the male mouse to 2,2',3,3',4,4',5,5',6,6'-decabrominated diphenyl ether: decreased epididymal sperm functions without alterations in DNA content and histology in testis |journal=Toxicology |volume=224 |issue=1–2 |pages=33–43 |date=July 2006 |pmid=16713668 |doi=10.1016/j.tox.2006.04.003 |name-list-
===Neurological effects===
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==Overall risks and benefits==
In 2002–2003 the American Chemistry
==Voluntary and governmental actions==
===Europe===
In [[Germany]], plastics manufacturers and the textile additives industry "declared in 1986 a voluntary phase-out of the use of PBDEs, including Deca-BDE."<ref name=Lassen2006>Lassen, Carsten, et al. [http://www2.mst.dk/Udgiv/publications/2007/978-87-7052-349-3/pdf/978-87-7052-350-9.pdf Deca-BDE and Alternatives in Electrical and Electronic Equipment.] Danish Environmental Protection Agency, 2006.</ref> Although decaBDE was to be phased out of electrical and electronic equipment in the EU by 2006 under the EU's [[Restriction of Hazardous Substances Directive]] (RoHS), decaBDE use has been exempted from RoHS during
DecaBDE has been the subject of a ten-year evaluation under the EU Risk Assessment procedure which has reviewed over 1100 studies. The Risk Assessment was published on the EU Official Journal in May 2008.<ref>Official Journal of the European Union: ''[http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:C:2008:131:0007:0012:EN:PDF Communication from the Commission on the results of the risk evaluation of chlorodifluoromethane, bis(pentabromophenyl)ether and methenamine and on the risk reduction strategy for the substance methenamine]'', 29.5.2008</ref> Deca was registered under the
The
On 5 July ECHA withdrew Deca-BDE from its list of priority substances for Authorisation under REACH, therefore closing the public consultation. On 1 August 2014, [[ECHA]] submitted a restriction proposal for Deca-BDE. The agency is proposing a restriction on the manufacture, use and placing on the market of the substance and of mixtures and articles containing it. On 17 September 2014, ECHA submitted the restriction report which initiates a six months public consultation. On 9 February 2017, the [[European Commission]] adopted Regulation EU 2017/227. Article 1 of this regulation states that Regulation (EC) No 1907/2006 is amended to include a ban on the use of decaBDE in quantities greater than 0.1% by weight, effective from 2 March 2019. Products placed on the market prior to 2 March 2019 are exempt. Furthermore, the use decaBDE in aircraft is permissible until 2 March 2027.<ref name="Commission Regulation (EU) 2017/227">{{cite journal|last1=The European Commission|title=Commission Regulation (EU) 2017/227|journal=Official Journal of the European Union|date=9 February 2017|volume=L35|pages=6–9|url=http://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32017R0227&from=EN|accessdate=16 June 2017}}</ref>
This EU process is running in parallel with a UNEP review to determine whether Deca-BDE should be listed as a [[Persistent Organic Pollutant]] (POP) under the Stockholm Convention.
===United States===
As of mid-2007 two states had instituted measures to phase out decaBDE. In April 2007 the state of [[Washington (U.S. state)|Washington]] passed a law banning the manufacture, sale, and use of decaBDE in mattresses as of 2008; the ban "could be extended to TVs, computers and upholstered residential furniture in 2011 provided an alternative flame retardant is approved."<ref name=Stiffler2007April>Stiffler, Lisa. [http://www.seattlepi.com/local/311845_pbdes17.html Chemical ban puts industry on the defensive.] ''Seattle Post-Intelligencer'', April 16, 2007.</ref><ref>{{Cite web |url=http://www.ecy.wa.gov/laws-rules/leg_imp/2007/1024.pdf |title=Archived copy |access-date=2012-12-15 |archive-url=https://web.archive.org/web/20150402122352/http://www.ecy.wa.gov/laws-rules/leg_imp/2007/1024.pdf |archive-date=2015-04-02 |
On December 17, 2009, as the result of negotiations with EPA, the two U.S. producers of decabromodiphenyl ether (decaBDE), Albemarle Corporation and Chemtura Corporation, and the largest U.S. importer, ICL Industrial Products, Inc., announced commitments to phase out voluntarily decaBDE in the United States by the end of 2013.[http://www.albemarle.com/?news=text&releaseID=1367378][http://phoenix.corporate-ir.net/phoenix.zhtml?c=68079&p=irol-newsArticle&ID=1367410&highlight] {{Webarchive|url=https://web.archive.org/web/20160119061747/http://phoenix.corporate-ir.net/phoenix.zhtml?c=68079&p=irol-newsArticle&ID=1367410&highlight |date=2016-01-19 }}, [https://web.archive.org/web/20110713001745/http://www.icl-ip.com/Brome/Brome.nsf/viewAllByUNID/6E5934724F9A52BEC22576930042E95A/%24file/Press_Release.pdf], [https://web.archive.org/web/20100118092730/http://www.epa.gov/oppt/existingchemicals/pubs/actionplans/deccadbe.html]
==Alternatives==
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==References==
{{Reflist
{{DEFAULTSORT:Decabromodiphenyl Ether}}
[[Category:Flame retardants]]
[[Category:
[[Category:PBT substances]]
[[Category:Persistent organic pollutants under the Stockholm Convention]]
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