Structural characterization and thermal stabilities of the isomers of the brominated flame retardant 1,2,5,6-tetrabromocyclooctane (TBCO)

Chemosphere

Volumn 74, Issue 11, 2009, Pages 1538-1543

  Riddell, Nicole ^a   Arsenault, Gilles ^a   Klein, Jeff ^a   Lough, Alan ^b   Marvin, Chris H ^c   McAlees, Alan ^a   McCrindle, Robert ^d   MacInnis, Gordia ^c   Sverko, Ed ^c   Tittlemier, Sheryl ^e   Tomy, Gregg T ^f  

^a Research Division   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c ENVIRONMENT CANADA   (Canada)

^d UNIVERSITY OF GUELPH   (Canada)

^e FOOD RESEARCH DIVISION   (Canada)

^f FISHERIES AND OCEANS CANADA   (Canada)

Author keywords

BFR; Conformation; Crystal structure; GC MS; LC MS; NMR spectroscopy

Indexed keywords

A THERMALS; ACQUITY; ANALYTICAL CHALLENGES; BFR; BROMIDE IONS; BROMINATED FLAME RETARDANTS; CAPILLARY COLUMNS; CHROMATOGRAPHIC STATIONARY PHASIS; DIASTEREOMERS; FRAGMENT IONS; GC/MS; H NMR SPECTROSCOPIES; INJECTOR TEMPERATURES; LC/MS; MASS SPECTRUM; MOBILE PHASE; MOLECULAR IONS; NMR SPECTROSCOPY; STRUCTURAL CHARACTERIZATIONS; STRUCTURAL ELUCIDATIONS; THERMAL INTERCONVERSION; THERMAL STABILITIES; WEAK INTENSITIES; X-RAY STRUCTURES;

CHROMATOGRAPHIC ANALYSIS; CRYSTAL STRUCTURE; FIRE FIGHTING EQUIPMENT; FLAME RETARDANTS; ION SOURCES; IONS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; STEREOCHEMISTRY;

ISOMERS;

BROMINE COMPOUND; CRYSTAL CHEMISTRY; EQUILIBRIUM; SPECTROSCOPY; THERMAL ALTERATION; THERMODYNAMIC PROPERTY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLOGRAPHY, X-RAY; CYCLOOCTANES; DRUG STABILITY; FLAME RETARDANTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HOT TEMPERATURE; HYDROCARBONS, BROMINATED; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 60649104601     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2008.11.026     Document Type: Article

References (16)

1. Allen F.H., Kennard O., Watson D.G., Brammer L., Orpen A.G., and Taylor R. Tables of bond lengths determined by X-ray and neutron diffraction part 1. Bond lengths in organic compounds. J. Chem. Soc. Perkin Trans. 2 (1987) S1-19
2. Arsenault G., Lough A., Marvin C., MacInnis G., McAlees A., McCrindle R., Pleskach K., Potter D., Riddell N., Sverko E., Tittlemier S., and Tomy G.T. Structure characterization and thermal stabilities of the isomers of the brominated flame retardant 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane. Chemosphere 72 (2008) 1163-1170
3. Blessing R.H. An empirical correction for absorption anisotropy. Acta Crystallogr. A 51 (1995) 33-38
4. Danish EPA Report, 1999. Appendix 3 on "physical chemical properties of brominated flame retardants" (http://www2.mst.dk/udgiv/Publications/1999/87-7909-416-3/html/bil03_eng.htm).
5. de Boer J., and Wells D.E. Pitfalls in the analysis of brominated flame retardants in environmental, human and food samples - including results of three international interlaboratory studies. Trends Anal. Chem. 25 (2006) 364-372
6. Fisk, P.R., Girling, A.E., Wildey, R.J., 2003. Prioritisation of flame retardants for environmental risk assessment, UK Environment Science Agency, pp. 1-129. (http://www.ec.europa.eu/environment/waste/stakeholders/industry_assoc/ebfrip/annex2.pdf).
7. Ferguson G., MacNicol D.D., Oberhansli W., Raphael R.A., and Zabkiewicz J.A. The conformation of trans-syn-trans-1,2,5,6-tetrabromocyclo-octane. Chem. Commun. (1968) 103-104
8. Heeb N.V., Schweizer W.B., Mattrel P., Haag R., Kohler M., Schmid P., Zennegg M., and Wolfensberger M. Regio- and stereoselective isomerization of hexabromocyclododecanes (HBCDs): kinetics and mechanism of (-HBCD racemization. Chemosphere 71 (2008) 1547-1556
9. Groweiss A., Hermolin J., and Goldberg I. Bromination of 1Z,5E,9E-cyclodecatrienes - a chemist's perspective. Advances in Organobromine Chemistry (1991), Elsevier 61-67
10. Köppen R., Becker R., Jung C., and Nehls I. On the thermally induced isomerisation of hexabromocyclododecane stereoisomers. Chemosphere 71 (2008) 656-662
11. Otwinowski Z., and Minor W. Methods in enzymology. In: Carter C.W., and Sweet R.M. (Eds). Macromolecular Crystallography Part A vol. 276 (1997), Academic press 307-326
12. Rohringer, P., Lohmann, F., Wurster, R.F., 1978. Agent for flame proofing synthetic fibrous material, September 26, US patent 4116702.
13. Sheldrick, G.M., 2001. SHELXTL/PC. Version 6.1 Windows NT Version, Bruker AXS Inc., Madison, USA.
14. Sonnenberg, F., Taristo, K.M., Johansson, T.V.J., 2001. Treatment for reducing residual carbon in the lost foam process, October 16, US patent 6303664.
15. Tashiro, M., Sakashita, N., Tatsuoka, Y., Mitamura, T., Orii, K., 1988. Flameproofing synthetic fiber, January 26, US patent 4721746.
16. Zitko V. TLC detection of brominated flame retardants in Styrofoam. Chemosphere 28 (1994) 1211-1215