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Enantioselective Analytical- and Preparative-Scale Separation of Hexabromocyclododecane Stereoisomers Using Packed Column Supercritical Fluid Chromatography
Örebro University, School of Science and Technology. Wellington Laboratories Inc., Guelph, Canada. (Man-Technology-Environment (MTM) Research Center)
Örebro University, School of Science and Technology. Waters Corporation, Milford, USA. (Man-Technology-Environment (MTM) Research Center)
Örebro University, School of Science and Technology. Norwegian Institute for Water Research, Oslo, Norway. (Man-Technology-Environment (MTM) Research Center)ORCID iD: 0000-0001-6217-8857
Örebro University, School of Science and Technology. (Man-Technology-Environment (MTM) Research Center)ORCID iD: 0000-0002-6330-789X
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2016 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 21, no 11, 1509Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
Basel, Switzerland: MDPI AG , 2016. Vol. 21, no 11, 1509
Keyword [en]
hexabromocyclododecane, enantiomeric separation, supercritical fluid chromatography
National Category
Analytical Chemistry
Identifiers
URN: urn:nbn:se:oru:diva-53487DOI: 10.3390/molecules21111509ISI: 000389918200091PubMedID: 27834934Scopus ID: 2-s2.0-84997428723OAI: oai:DiVA.org:oru-53487DiVA: diva2:1046735
Available from: 2016-11-15 Created: 2016-11-14 Last updated: 2017-10-18Bibliographically approved
In thesis
1. Packed Column Supercritical Fluid Chromatography: Applications in Environmental Chemistry
Open this publication in new window or tab >>Packed Column Supercritical Fluid Chromatography: Applications in Environmental Chemistry
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Although gas and liquid chromatography have emerged as dominant separation techniques in environmental analytical chemistry, these methods do not allow for the concurrent analysis of chemically diverse groups of persistent organic pollutants (POPs). There are also a small number of compounds which are not easily amenable to either of these traditional separation techniques. The main objective of this thesis was to address these issues by demonstrating the applicability of packed column supercritical fluid chromatography (pSFC) coupled to mass spectrometry (MS) in various aspects of environmental chemistry.

First, pSFC/MS analytical methods were developed for legacy POPs (PCDDs, PCDFs, and PCBs) as well as the emerging environmental contaminant Dechlorane Plus (DP), and issues relating to the ionization of target analytes when pSFC was coupled to MS were explored. Novel APPI and APCI reagents (fluorobenzene and triethylamine) were optimized and real samples (water and soil) were analyzed to demonstrate environmental applicability.

The possibility of chiral and preparative scale pSFC separations was then demonstrated through the isolation and characterization of thermally labile hexabromocyclododecane (HBCDD) stereoisomers. The analytical pSFC separation of the α-, β-, and γ-HBCDD enantiomers as well as the δ and ε meso forms was shown to be superior to results obtained using a published LC method.

Finally, technical mixtures of phosphorus flame retardants (RBDPP, BPA-BDPP, and DOPO; a group of related compounds which are challenging to analyze concurrently) were examined using multiple analytical techniques and pSFC was found to be the only method which facilitated the accurate determination of the components of all 3 mixtures. This thesis confirms the potential of pSFC/MS as a fast, green, and cost effective means of separating and analyzing environmental contaminants.

Place, publisher, year, edition, pages
Örebro: Örebro University, 2017. 87 p.
Series
Örebro Studies in Chemistry, ISSN 1651-4270 ; 19
Keyword
Supercritical Fluid Chromatography, Mass Spectrometry, Ionization, POPs, APPI, APCI, chiral, achiral, packed column
National Category
Other Chemistry Topics
Identifiers
urn:nbn:se:oru:diva-56826 (URN)978-91-7529-184-0 (ISBN)
Public defence
2017-05-12, Örebro universitet, Billbergska huset, Hörsal B, Fakultetsgatan 1, Örebro, 10:15 (English)
Opponent
Supervisors
Available from: 2017-03-27 Created: 2017-03-27 Last updated: 2017-10-18Bibliographically approved

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