2,5,6,9,10-Pentabromocyclododecanols (PBCDOHs): A new class of HBCD transformation products

Chemosphere

Volumn 88, Issue 5, 2012, Pages 655-662

  Heeb, Norbert V ^a   Zindel, Daniel ^a,b   Bernd Schweizer, W ^c   Lienemann, Peter ^b  

^a SWISS FEDERAL LABORATORIES FOR MATERIALS SCIENCE AND TECHNOLOGY   (Switzerland)

^b ZURICH UNIVERSITY OF APPLIED SCIENCES   (Switzerland)

^c ETH ZURICH   (Switzerland)

Author keywords

Brominated flame retardants; Crystal structure; HBCD transformation products; HBCDD; Stereoisomers

Indexed keywords

ENANTIOMERS; FLAME RETARDANTS; MASS SPECTROMETRY; METABOLITES; POLYSTYRENES; STEREOCHEMISTRY;

BROMINATED FLAME RETARDANTS; CRYSTAL STRUCTURE ANALYSIS; HBCDD; HEXABROMOCYCLODODECANES; MASS SPECTROMETRIC DATA; STEREOISOMERS; TRANSFORMATION PRODUCTS; TRANSFORMATION REACTIONS;

CRYSTAL STRUCTURE;

2,5,6,9,10 PENTABROMOCYCLODODECANOL; CYCLODODECATRIENE; HEXABROMOCYCLODODECANE; ISOBUTANOL; ISOBUTOXYPENTABROMOCYCLODODECANE; POLYSTYRENE; UNCLASSIFIED DRUG;

ALCOHOL; BIOTRANSFORMATION; BROMINE COMPOUND; CRYSTAL STRUCTURE; MASS SPECTROMETRY; METABOLITE; PLASTIC; POLYMER; TRANSFORMATION;

ARTICLE; BROMINATION; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOMER; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 84861183801     PISSN: 00456535     EISSN: 18791298     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2012.03.052     Document Type: Article

References (43)

1. Alaee M., Arias P., Sjödin A., Bergman A. An overview of commercially used brominated flame retardants, their applications, their use patterns in different countries/regions and possible modes of release. Environ. Int. 2003, 29:683-689.
2. Bogdal C., Schmid P., Zennegg M., Blüthgen N., Anselmetti F.S., Kohler M., Heeb N.V., Scheringer M., Hungerbühler K. Temporal trends of hexabromocyclododecanes in urban, rural and remote lakes in Switzerland. Organohalogen Compd. 2010, 72:338-341.
3. Brandsma S.H., van der Ven L.T.M., de Boer J., Leonards P.E.G. Identification of hydroxylated metabolites of hexabromocyclododecanes in wildlife and 28-days exposed wistar rats. Environ. Sci. Technol. 2009, 43:6058-6063.
4. Browne M.A., Dissanayake A., Galloway T.S., Lowe D.M., Thompson R.C. Ingested microscopic plastic translocates to the circulatory system of the mussel, Mytilus edulis (L.). Environ. Sci. Technol. 2008, 42:5026-5031.
5. Bruker, 2010. SAINT Release 7.68A. Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, USA.
6. Covaci A., Gerecke A.C., Law R.J., Voorspoels S., Kohler M., Heeb N.V., Leslie H., Allchin C.R., De Boer J. Hexabromocyclododecanes (HBCDs) in the environment and humans: a review. Environ. Sci. Technol. 2006, 40:3679-3688.
7. de Wit C.A. An overview of brominated flame retardants in the environment. Chemosphere 2002, 46:583-624.
8. de Wit C.A., Alaee M., Muir D.C.C. Levels and trends of brominated flame retardants in the Arctic. Chemosphere 2006, 64:209-233.
9. Derraik J.G.B. The pollution of the marine environment by plastic debris: a review. Mar. Pollut. Bull. 2002, 44:842-852.
10. Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A.K., Puschmann H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. 2009, 42:339-341.
11. Dunitz J.D., Shearer H.M.M. Die strukturen der mittleren ringverbindungen-III. Die struktur des cyclododecans. Helv. Chim. Acta 1960, 43:18-35.
12. ECB, European Chemicals Bureau, 2010. Identification of PBT and VPVB substances. http://ecb.jrc.ec.europa.eu/documents/PBT_EVALUATION/PBT_sum058_CAS_25637-99-4.pdf.
13. Esslinger S., Becker R., Maul R., Nehls I. Hexabromocyclododecane enantiomers: microsomal degradation and patterns of hydroxylated metabolites. Environ. Sci. Technol. 2011, 45:3938-3944.
14. Flack H.D. Acta Cryst. 1983, A39:876-881.
15. Gerecke A.C., Kohler M., Zennegg M., Schmid P., Heeb N.V. Detection of α-isomer dominated HBCD (hexabromocyclododecane) in Swiss fish at levels comparable to PBDEs (polybrominated diphenyl ethers). Organohalogen Compd. 2003, 61:155-158.
16. Heeb N.V., Schweizer W.B., Kohler M., Gerecke A.C. Structure elucidation of hexabromocyclododecanes - a class of compounds with a complex stereochemistry. Chemosphere 2005, 61:65-73.
17. Heeb N.V., Schweizer W.B., Haag R., Mattrel P., Kohler M. Crystal structure analysis of enantiomerically pure (+) and (-) β-hexabromocyclododecanes. Chemosphere 2007, 66:1590-1594.
18. Heeb N.V., Schweizer W.B., Mattrel P., Haag R., Gerecke A.C., Kohler M., Schmid P., Zennegg M., Wolfensberger M. Solid-state conformations and absolute configurations of (+) and (-) α-, β-, and γ-hexabromocyclododecanes (HBCDs). Chemosphere 2007, 68:940-950.
19. Heeb N.V., Schweizer W.B., Mattrel P., Haag R., Gerecke A.C., Schmid P., Zennegg M., Vonmont H. Regio- and stereoselective isomerization of hexabromocyclododecanes (HBCDs): kinetics and mechanism of γ- to α-HBCD isomerization. Chemosphere 2008, 73:1201-1210.
20. Heeb N.V., Schweizer W.B., Mattrel P., Haag R., Kohler M., Schmid P., Zennegg M., Wolfensberger M. Regio- and stereoselective isomerization of hexabromocyclododecanes (HBCDs): kinetics and mechanism of β-HBCD racemization. Chemosphere 2008, 71:1547-1556.
21. Heeb N.V., Graf H., Schweizer W.B., Lienemann P. Isobutoxypentabromocyclododecanes (iBPBCDs): a new class of polybrominated compounds. Chemosphere 2010, 78:950-957.
22. Heeb N.V., Graf H., Schweizer W.B., Lienemann P. Thermally-induced transformation of hexabromocyclododecanes and isobutoxypentabromo-cyclododecanes in flame-proofed polystyrene materials. Chemosphere 2010, 80:701-708.
23. Heeb N.V., Graf H., Schweizer W.B., Heeb M., Lienemann P. Crystal structure of δ-isobutoxypentabromo-cyclododecanes, kinetics and selectivity of their isomerization during thermal treatment of flame-proofed polystyrenes. Chemosphere 2011, 83:1568-1574.
24. Janak K., Covaci A., Voorspoels S., Becher G. Hexabromocyclododecane (HBCD) in marine species from the Western Scheldt estuary: diastereomer- and enantiomer-specific accumulation. Environ. Sci. Technol. 2005, 39:1987-1994.
25. Kohler M., Zennegg M., Bogdal C., Gerecke A.C., Schmid P., Heeb N.V., Sturm M., Vonmont H., Kohler H.-P., Giger W. Temporal trends, congener patterns, and sources of octa-, nona-, and deca-bromodiphenyl ethers (PBDEs) and hexabromocyclododecanes (HBCDs) in Swiss lake sediments. Environ. Sci. Technol. 2008, 42:6378-6384.
26. Law R.J., Alaee M., Allchin C.R., Boon J.P., Lebeuf M., Lepom P., Stern G.A. Levels and trends of polybrominated diphenylethers and other brominated flame retardants in wildlife. Environ. Int. 2003, 29:757-770.
27. Law R.J., Kohler M., Heeb N.V., Gerecke A.C., Schmid P., Voorspoels S., Covaci A., Becher G., Janak K., Thomsen C. Hexabromocyclododecanes challenge scientists and regulators. Environ. Sci. Technol. 2005, 39:281A-287A.
28. Law R.J., Allchin C.R., de Boer J., Covaci A., Herzke D., Lepom P., Morris S., Tronczynski J., de Wit C.A. Levels and trends of brominated flame retardants in the European environment. Chemosphere 2006, 64:187-208.
29. Lindberg P., Sellström U., Häggberg L., de Wit C.A. Higher brominated diphenyl ethers and hexabromocyclododecane found in eggs of peregrine falcons (Falco peregrinus) breeding in Sweden. Environ. Sci. Technol. 2004, 38:93-96.
30. Marvin C.H., Tomy G.T., Alaee M., MacInnis G. Distribution of hexabromocyclododecanes in Detroit River suspended sediments. Chemosphere 2006, 64:268-275.
31. Moore C.J., Moore S.L., Leecaster M.K., Weisberg S.B. A comparison of plastic and plankton in the North Pacific central gyre. Mar. Pollut. Bull. 2001, 42:1297-1300.
32. Peck A.M., Pugh R.S., Moors A., Ellisor M.B., Porter B.J., Becker P.R., Kucklick J.R. Hexabromocyclododecane in white-sided dolphins: temporal trend and stereoisomer distribution in tissues. Environ. Sci. Technol. 2008, 42:2650-2655.
33. Ransford, G., United States Patent 5043492, 1991. Method for producing hexabromocyclododecane. http://www.freepatentsonline.com/5043492.
34. Remberger M., Sternbeck J., Palm A., Kaj L., Strömberg K., Brorström-Lundén E. The environmental occurrence of hexabromocyclododecane in Sweden. Chemosphere 2004, 54:9-21.
35. Sellström U., Kierkegaard A., de Wit C.A., Jansson B. Polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from a Swedish river. Environ. Toxicol. Chem. 1998, 17:1065-1072.
36. Sellström U., Bignert A., Kierkegaard A., Häggberg L., de Wit C., Olsson M., Jansson B. Temporal trend studies on tetra- and pentabrominated diphenyl ethers and hexabromocyclododecane in guillemot egg from the Baltic sea. Environ. Sci. Technol. 2003, 37:5496-5501.
37. Sheldrick G.M. Acta Cryst. 2008, A64:112-122.
38. Thomsen C., Froshaug M., Broadwell S.L., Becher G. Levels of brominated flame retardants in milk from the Norwegian human milk study: HUMIS. Organohalogen Compd. 2005, 67:509-512.
39. Thomsen C., Stigum H., Froshaug M., Broadwell S.L., Becher G., Eggesbo M. Determinants of brominated flame retardants in breast milk from a large scale Norwegian study. Environ. Int. 2010, 36:68-74.
40. Thompson R.C., Olsen Y., Mitchell R.P., Davis A., Rowland S.J., John A.W.G., McGonigle D., Russell A. Lost at sea: where is all the plastic?. Science 2004, 304:838.
41. Tomy G.T., Budakowski W., Halldorson T., Whittle D.M., Keir M.J., Marvin C., Macinnis G., Alaee M. Biomagnification of alpha- and gamma-hexabromocyclododecane isomers in a Lake Ontario food web. Environ. Sci. Technol. 2004, 38:2298-2303.
42. Weiss J., Meijer L., Sauer P., Linderholm L., Athanasiadis I., Bergman A. PBDE and HBCD levels in blood from Dutch mothers and infants - analysis of a Dutch Groningen infant cohort. Organohalogen Compd. 2004, 66:2677-2682.
43. Wünsch, J.R., 2000. Polystyrene: synthesis, production and application Vol. 10, Report 112. iSmithers Rapra Publishing, Shawbury, Great Britan.