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Molecules 2016, 21(11), 1509; doi:10.3390/molecules21111509

Enantioselective Analytical- and Preparative-Scale Separation of Hexabromocyclododecane Stereoisomers Using Packed Column Supercritical Fluid Chromatography

1
Wellington Laboratories Inc., 345 Southgate Drive, Guelph, ON N1G 3M5, Canada
2
Man-Technology-Environment (MTM) Research Center, Örebro University, 70182 Örebro, Sweden
3
Waters Corporation, 34 Maple Street, Milford, MA 01757, USA
4
Norwegian Institute for Water Research, NO-349 Oslo, Norway
5
Department of Chemistry, University of Toronto, Toronto, ON M5S 3H6, Canada
6
Chemistry Department, University of Guelph, Guelph, ON N1G 2W1, Canada
*
Author to whom correspondence should be addressed.
Academic Editor: Yoshio Okamoto
Received: 14 October 2016 / Revised: 4 November 2016 / Accepted: 7 November 2016 / Published: 10 November 2016
View Full-Text   |   Download PDF [885 KB, uploaded 10 November 2016]   |  

Abstract

Hexabromocyclododecane (HBCDD) is an additive brominated flame retardant which has been listed in Annex A of the Stockholm Convention for elimination of production and use. It has been reported to persist in the environment and has the potential for enantiomer-specific degradation, accumulation, or both, making enantioselective analyses increasingly important. The six main stereoisomers of technical HBCDD (i.e., the (+) and (−) enantiomers of α-, β-, and γ-HBCDD) were separated and isolated for the first time using enantioselective packed column supercritical fluid chromatography (pSFC) separation methods on a preparative scale. Characterization was completed using published chiral liquid chromatography (LC) methods and elution profiles, as well as X-ray crystallography, and the isolated fractions were definitively identified. Additionally, the resolution of the enantiomers, along with two minor components of the technical product (δ- and ε-HBCDD), was investigated on an analytical scale using both LC and pSFC separation techniques, and changes in elution order were highlighted. Baseline separation of all HBCDD enantiomers was achieved by pSFC on an analytical scale using a cellulose-based column. The described method emphasizes the potential associated with pSFC as a green method of isolating and analyzing environmental contaminants of concern. View Full-Text
Keywords: hexabromocyclododecane; enantiomeric separation; supercritical fluid chromatography hexabromocyclododecane; enantiomeric separation; supercritical fluid chromatography
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MDPI and ACS Style

Riddell, N.; Mullin, L.G.; van Bavel, B.; Ericson Jogsten, I.; McAlees, A.; Brazeau, A.; Synnott, S.; Lough, A.; McCrindle, R.; Chittim, B. Enantioselective Analytical- and Preparative-Scale Separation of Hexabromocyclododecane Stereoisomers Using Packed Column Supercritical Fluid Chromatography. Molecules 2016, 21, 1509.

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