|Jmol-3D images||Image 1|
|Molar mass||641.7 g/mol|
|Melting point||186 °C (175–195 °C, depending upon isomer)|
|Solubility in water||3.4 µg/L in water|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Hexabromocyclododecane (HBCD or HBCDD) 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. HBCD is highly efficient in this application so that very low levels are required to reach the desired flame retardancy. Typical HBCD levels in EPS are 0.7% and in XPS 2.5%. At present, according to BSEF, the brominated flame retardant industry panel, HBCD is the only suitable flame retardant for these applications. Any other flame retardant would likely need higher load levels in the polystyrene foam. 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”.
HBCD's toxicity and its harm to the environment are currently discussed. HBCD can be found in environmental samples such as birds, mammals, fish and other aquatic organisms as well as soil and sediment. On this basis, on 28 October 2008 the European Chemicals Agency decided to include HBCD in the SVHC list, Substances of Very High Concern, within the Registration, Evaluation, Authorisation and Restriction of Chemicals framework. HBCD has been found widely present in biological samples from remote areas and supporting evidences for its classification as Persistent, Bioaccumulative and Toxic (PBT) and undergoes long-range environmental transportation. In July 2012, an EU harmonised classification and labelling for HBCD entered into force. HBCD has been classified as a category 2 for reproductive toxicity. Since August 2010 hexabromocyclododecanes are included in the EPA's List of Chemicals of Concern. On 19 October 2012 the Persistent Organic Pollutants Review Committee, a subsidiary body of the Stockholm Convention on Persistent Organic Pollutants (POPs), adopted a recommendation to include HBCD in the Convention’s Annex A for elimination, with specific exemptions for expanded and extruded polystyrene needed to give countries time to phase-in safer substitutes. Final decision will be taken in May 2013.
Because HBCD has 16 possible stereo-isomers with different biological activities, the substance poses a difficult problem for manufacture and regulation. The HBCD commercial mixture is composed of three main diastereomers denoted as alpha (α-HBCD), beta (β-HBCD) and gamma (γ-HBCD) with traces of others. A series of four published in vivo mice studies were conducted between several federal and academic institutions to characterize the toxicokinetic profiles of individual HBCD stereoisomers. The predominant diastereomer in the HBCD mixture, γ-HBCD, undergoes rapid hepatic metabolism, fecal and urinary elimination, and biological conversion to other diastereomers with a short biological half-life of 1-4 days. After oral exposure to the γ-HBCD diastereomer, β-HBCD was detected in the liver and brain, and α-HBCD and β-HBCD was detected in the fat and feces  with multiple novel metabolites identified - monohydroxy-pentabromocyclododecane, monohydroxy-pentabromocyclododecene, dihydroxy-pentabromocyclododecene, and dihydroxy-pentabromocyclododecadiene.  In contrast, α-HBCD is more biologically persistent, resistant to metabolism, bioaccumulates in lipid-rich tissues after a 10 day repeated exposure study, and has a longer biological half-life of up to 21 days; only α-HBCD was detected in the liver, brain, fat and feces with no stereoisomerization to γ-HBCD or β-HBCD and low trace levels of four different hydroxylated metabolites were identified.  Developing mice had higher HBCD tissue levels than adult mice after exposure to either α-HBCD or γ-HBCD indicating the potential for increased susceptibility of the developing young to HBCD effects. The reported toxicokinetic differences of individual HBCD diastereoisomers have important implications for the extrapolation of toxicological studies of the commercial HBCD mixture to the assessment of human risk.
|This article is outdated. (March 2014)|
Due to its persistence, toxicity, and ecotoxicity, a global ban on HBCD is currently being considered under the framework of the Stockholm Convention on Persistent Organic Pollutants. It was proposed banned by the Stockholm Convention in October 2012, final decision will be taken May 2013 (see above). HBCD is also included on the list of substances added to a proposal to revise the RoHS (Restriction of Hazardous Substances) directive. There is a large and increasing stock of HBCD in the anthroposphere, mainly in EPS and XPS insulation boards.
The Persistent Organic Pollutants Review Committee of the Stockholm Convention announced on 2012-10-25 that it is recommending the listing of hexabromocyclododecane in Annex A to the Convention with specific exemptions for production and use in expanded polystyrene and extruded polystyrene in buildings.
|Wikimedia Commons has media related to Hexabromocyclododecanes.|
- ^ UNEP Stockholm Convention HBCD Risk management evaluation http://chm.pops.int/Convention/POPsReviewCommittee/Chemicals/tabid/243/Default.aspx
- Covaci, A; Gerecke, AC; Law, RJ; Voorspoels, S; Kohler, M; Heeb, NV; Leslie, H; Allchin, CR; De Boer, J (2006). "Hexabromocyclododecanes (HBCDs) in the environment and humans: A review". Environmental Science & Technology 40 (12): 3679–88. doi:10.1021/es0602492. PMID 16830527.
- "ECHA SVHC Official List". Echa.europa.eu. 2011-12-19. Retrieved 2012-06-20.
- "ECHA HBCD SVHC Supporting Documentation". Echa.europa.eu. Retrieved 2012-06-20.
- 5. Commission Regulation (EU) No 618/2012 of 10 July 2012 amending, for the purposes of its adaptation to technical and scientific progress, Regulation (EC) No 1272/2008 of the European Parliament and of the Council on classification, labelling and packaging of substances and mixtures.http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2012:179:0003:0010:EN:PDF
- "EPA action details on HBCD". Epa.gov. Retrieved 2012-06-20.
- "Press release from Stockholm Convention".
- "Hexabromocyclododecane Challenges Scientists and Regulators". Retrieved 2012-06-20.
- Szabo DT, Diliberto JJ, Hakk H, Huwe JK, Birnbaum LS; Diliberto; Hakk; Huwe; Birnbaum (2010). "Toxicokinetics of the flame retardant hexabromocyclododecane gamma: effect of dose, timing, route, repeated exposure, and metabolism". Toxicological Sciences 117 (2): 282–93. doi:10.1093/toxsci/kfq183. PMID 20562218.
- Hakk H, Szabo DT, Huwe J, Diliberto J, Birnbaum LS; Szabo; Huwe; Diliberto; Birnbaum (2012). "Novel and distinct metabolites identified following a single oral dose of α- or γ-hexabromocyclododecane in mice". Environmental Science and Technology 46 (24): 13494–503. doi:10.1021/es303209g. PMC 3608416. PMID 23171393.
- Szabo DT, Diliberto JJ, Hakk H, Huwe JK, Birnbaum LS; Diliberto; Hakk; Huwe; Birnbaum (2011). "Toxicokinetics of the flame retardant hexabromocyclododecane alpha: effect of dose, timing, route, repeated exposure, and metabolism". Toxicological Sciences 121 (2): 234–44. doi:10.1093/toxsci/kfr059. PMID 21441408.
- Szabo DT, Diliberto JJ, Huwe JK, Birnbaum LS; Diliberto; Huwe; Birnbaum (2011). "Differences in tissue distribution of HBCD alpha and gamma between adult and developing mice". Toxicological Sciences 123 (1): 256–63. doi:10.1093/toxsci/kfr161. PMID 21705717.
- "Stockholm Convention: Newly Proposed Chemicals". Retrieved 2008-12-05.
- RoHS Directive, proposed changes, December 2008
- 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
- "Proposal to amend Annex A to the Stockholm Convention to be discussed at the sixth meeting of the Conference of the Parties". Retrieved 2012-10-29.
- MPI Milebrome B-972, FR 50 & GC SAM: The low cost alternatives to Hexabromocyclododecane (HBCD) in EPS and XPS applications, Stockholm Convention on Persistent Organic Pollutants 2012
- An Overview of Alternatives to Tetrabromobisphenol A (TBBPA) and Hexabromocyclododecane (HBCD), University of Massachusetts Lowell, March 2006
- ECHA: MEMBER STATE COMMITTEE SUPPORT DOCUMENT FOR IDENTIFICATION OF HEXABROMOCYCLODODECANE AND ALL MAJOR DIASTEREOISOMERS IDENTIFIED AS A SUBSTANCE OF VERY HIGH CONCERN, 8 October 2008
- Factsheet BSEF