decabromodiphenyl ethane
{{Chembox
| ImageFile = Decabromodiphenyl ethane.png
| IUPACName = 1,1'-ethane-1,2-diylbis(pentabromobenzene)
| OtherNames = {{ubl|1,2-Bis(perbromophenyl)ethane|1,2-Bis(2,3,4,5,6-pentabromophenyl)ethane|1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene }}
| Section1 = {{Chembox Identifiers
| CASNo = 84852-53-9
| CASNo_Ref = {{Cascite|correct|CAS}}
| ChemSpiderID = 9161088
| ChEMBL = 219257
| PubChem = 10985889
| EC_number = 284-366-9
| UNII = WZ2532TA0A
| SMILES = C(CC1=C(C(=C(C(=C1Br)Br)Br)Br)Br)C2=C(C(=C(C(=C2Br)Br)Br)Br)Br
| InChI = 1S/C14H4Br10/c15-5-3(6(16)10(20)13(23)9(5)19)1-2-4-7(17)11(21)14(24)12(22)8(4)18/h1-2H2
| StdInChIKey = BZQKBFHEWDPQHD-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=14 | H=4 | Br=10
| Appearance = White solid
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| GHS_ref=
| MainHazards =
| FlashPt =
| AutoignitionPt =
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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.{{Cite web |title=Substance Information – 1,1'-(ethane-1,2-diyl)bis[pentabromobenzene] |url=https://echa.europa.eu/substance-information/-/substanceinfo/100.076.669 |access-date=2023-01-09 |website=echa.europa.eu |language=en-GB |agency=ECHA}}
Uses
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.{{cite journal |last1=Xue |first1=Mianqiang |last2=Zhou |first2=Liang |last3=Kojima |first3=Naoya |last4=Machimura |first4=Takashi |last5=Tokai |first5=Akihiro |title=Decabromodiphenyl Ether (DecaBDE) in Electrical and Electronic Equipment in Japan: Stock, Emission, and Substitution Evaluation |journal=Environmental Science & Technology |date=21 November 2017 |volume=51 |issue=22 |pages=13224–13230 |doi=10.1021/acs.est.7b03656|pmid=29052980 |bibcode=2017EnST...5113224X }} 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.{{cite journal |last1=Shen |first1=Kaihui |last2=Li |first2=Li |last3=Liu |first3=Junzhou |last4=Chen |first4=Chengkang |last5=Liu |first5=Jianguo |title=Stocks, flows and emissions of DBDPE in China and its international distribution through products and waste |journal=Environmental Pollution |date=1 July 2019 |volume=250 |pages=79–86 |doi=10.1016/j.envpol.2019.03.090|pmid=30981938 |s2cid=109735570 }} 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. 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.{{Cite web |author=Ruedi Taverna |author2=Rolf Gloor |author3=Urs Maier |author4=Markus Zennegg |author5=Renato Figi |author6=Edy Birchler |year=2017 |title=Substance flows in Swiss e-waste (Summary) |url=https://www.bafu.admin.ch/uz-1717-e |access-date=2023-01-09 |agency=Federal Office for the Environment}}
Environmental occurrence
Decabromodiphenylethane was first detected in the environment in 2004.{{cite journal |last1=Kierkegaard |first1=Amelie |last2=Björklund |first2=Jonas |last3=Fridén |first3=Ulrika |title=Identification of the Flame Retardant Decabromodiphenyl Ethane in the Environment |journal=Environmental Science & Technology |date=1 June 2004 |volume=38 |issue=12 |pages=3247–3253 |doi=10.1021/es049867d|pmid=15260320 |bibcode=2004EnST...38.3247K }} It has been found in biota, air,{{cite journal |last1=Zhao |first1=Yifan |last2=Ma |first2=Jin |last3=Qiu |first3=Xinghua |last4=Lin |first4=Yan |last5=Yang |first5=Qiaoyun |last6=Zhu |first6=Tong |title=Gridded Field Observations of Polybrominated Diphenyl Ethers and Decabromodiphenyl Ethane in the Atmosphere of North China |journal=Environmental Science & Technology |date=18 July 2013 |volume=47 |issue=15 |pages=8123–8129 |doi=10.1021/es402193r|pmid=23837541 }} sediments,{{cite journal |last1=Ricklund |first1=Niklas |last2=Kierkegaard |first2=Amelie |last3=McLachlan |first3=Michael S. |title=Levels and Potential Sources of Decabromodiphenyl Ethane (DBDPE) and Decabromodiphenyl Ether (DecaBDE) in Lake and Marine Sediments in Sweden |journal=Environmental Science & Technology |date=15 March 2010 |volume=44 |issue=6 |pages=1987–1991 |doi=10.1021/es903701q|pmid=20146463 |bibcode=2010EnST...44.1987R }} sewage sludge,{{cite journal |last1=Ricklund |first1=Niklas |last2=Kierkegaard |first2=Amelie |last3=McLachlan |first3=Michael S. |title=An international survey of decabromodiphenyl ethane (deBDethane) and decabromodiphenyl ether (decaBDE) in sewage sludge samples |journal=Chemosphere |date=1 December 2008 |volume=73 |issue=11 |pages=1799–1804 |doi=10.1016/j.chemosphere.2008.08.047|pmid=18922559 |bibcode=2008Chmsp..73.1799R }} and house dust.{{cite journal |last1=Stapleton |first1=Heather M. |last2=Allen |first2=Joseph G. |last3=Kelly |first3=Shannon M. |last4=Konstantinov |first4=Alex |last5=Klosterhaus |first5=Susan |last6=Watkins |first6=Deborah |last7=McClean |first7=Michael D. |last8=Webster |first8=Thomas F. |title=Alternate and New Brominated Flame Retardants Detected in U.S. House Dust |journal=Environmental Science & Technology |date=15 September 2008 |volume=42 |issue=18 |pages=6910–6916 |doi=10.1021/es801070p|pmid=18853808 |bibcode=2008EnST...42.6910S }}