Decabromodiphenyl ethane

Decabromodiphenyl ethane is a chemical compound used as a brominated flame retardant. It was commercialised in the 1990s as an alternative for decabromodiphenyl ether,[1] 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.[2]

Decabromodiphenyl ethane
Names
IUPAC name
1,1'-ethane-1,2-diylbis(pentabromobenzene)
Other names
  • 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
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.076.669
EC Number
  • 284-366-9
UNII
  • Key: BZQKBFHEWDPQHD-UHFFFAOYSA-N
  • 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
  • C(CC1=C(C(=C(C(=C1Br)Br)Br)Br)Br)C2=C(C(=C(C(=C2Br)Br)Br)Br)Br
Properties
C14H4Br10
Molar mass 971.226 g·mol−1
Appearance White solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[3] 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.[4] 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.[2] 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.[5]

Environmental occurrence

Decabromodiphenylethane was first detected in the environment in 2004.[6] It has been found in biota, air,[7] sediments,[8] sewage sludge,[1] and house dust.[9]

References
  1. Ricklund, Niklas; Kierkegaard, Amelie; McLachlan, Michael S. (1 December 2008). "An international survey of decabromodiphenyl ethane (deBDethane) and decabromodiphenyl ether (decaBDE) in sewage sludge samples". Chemosphere. 73 (11): 1799–1804. Bibcode:2008Chmsp..73.1799R. doi:10.1016/j.chemosphere.2008.08.047. PMID 18922559.
  2. "Substance Information – 1,1'-(ethane-1,2-diyl)bis[pentabromobenzene]". echa.europa.eu. ECHA. Retrieved 2023-01-09.
  3. Xue, Mianqiang; Zhou, Liang; Kojima, Naoya; Machimura, Takashi; Tokai, Akihiro (21 November 2017). "Decabromodiphenyl Ether (DecaBDE) in Electrical and Electronic Equipment in Japan: Stock, Emission, and Substitution Evaluation". Environmental Science & Technology. 51 (22): 13224–13230. Bibcode:2017EnST...5113224X. doi:10.1021/acs.est.7b03656. PMID 29052980.
  4. Shen, Kaihui; Li, Li; Liu, Junzhou; Chen, Chengkang; Liu, Jianguo (1 July 2019). "Stocks, flows and emissions of DBDPE in China and its international distribution through products and waste". Environmental Pollution. 250: 79–86. doi:10.1016/j.envpol.2019.03.090. PMID 30981938. S2CID 109735570.
  5. Ruedi Taverna; Rolf Gloor; Urs Maier; Markus Zennegg; Renato Figi; Edy Birchler (2017). "Substance flows in Swiss e-waste (Summary)". Federal Office for the Environment. Retrieved 2023-01-09.
  6. Kierkegaard, Amelie; Björklund, Jonas; Fridén, Ulrika (1 June 2004). "Identification of the Flame Retardant Decabromodiphenyl Ethane in the Environment". Environmental Science & Technology. 38 (12): 3247–3253. Bibcode:2004EnST...38.3247K. doi:10.1021/es049867d. PMID 15260320.
  7. Zhao, Yifan; Ma, Jin; Qiu, Xinghua; Lin, Yan; Yang, Qiaoyun; Zhu, Tong (18 July 2013). "Gridded Field Observations of Polybrominated Diphenyl Ethers and Decabromodiphenyl Ethane in the Atmosphere of North China". Environmental Science & Technology. 47 (15): 8123–8129. doi:10.1021/es402193r. PMID 23837541.
  8. Ricklund, Niklas; Kierkegaard, Amelie; McLachlan, Michael S. (15 March 2010). "Levels and Potential Sources of Decabromodiphenyl Ethane (DBDPE) and Decabromodiphenyl Ether (DecaBDE) in Lake and Marine Sediments in Sweden". Environmental Science & Technology. 44 (6): 1987–1991. Bibcode:2010EnST...44.1987R. doi:10.1021/es903701q. PMID 20146463.
  9. Stapleton, Heather M.; Allen, Joseph G.; Kelly, Shannon M.; Konstantinov, Alex; Klosterhaus, Susan; Watkins, Deborah; McClean, Michael D.; Webster, Thomas F. (15 September 2008). "Alternate and New Brominated Flame Retardants Detected in U.S. House Dust". Environmental Science & Technology. 42 (18): 6910–6916. Bibcode:2008EnST...42.6910S. doi:10.1021/es801070p. PMID 18853808.
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