Chromatographic enrichment and enantiomer separation of axially chiral polybrominated biphenyls in a technical mixture

被引:23
作者
Berger, U
Vetter, W
Götsch, A
Kallenborn, R
机构
[1] Norwegian Inst Air Res NILU, Polar Environm Ctr, NO-9296 Tromso, Norway
[2] Univ Jena, Dept Food Chem, DE-07743 Jena, Germany
关键词
enantiomer separation; atropisomerism; Firemaster BP-6; polybrominated biphenyls; cyclodextrins;
D O I
10.1016/S0021-9673(02)01112-3
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The separation properties of different chromatographic methods regarding the enantioselective separation of axially chiral (atropisomeric) polybrominated biphenyls (PBB) were studied. For this purpose, the technical hexabromobiphenyl product Firemaster BP-6(R) was characterised by gas-chromatography coupled to electron capture detection (GC/ECD) and electron-capture negative ion mass spectrometry (GC/ECNI-MS) as well as by liquid chromatographic fractionating on active carbon and celite. Twelve individual PBBs including potential atropisomeric PBBs were isolated from Firemaster BP-6 by reversed-phase high-performance liquid chromatography (HPLC) on three serially coupled octadecylsilane columns. Six of the 12 isolated PBBs (three tri-ortho and di-ortho substituted PBBs, respectively) were separated into atropisomers on a HPLC column containing permethylated beta-cyclodextrin on silica. Moreover, the temperature dependency of the enantiomer separations is discussed. Gas chromatographic enantiomer separation of PBBs is a very demanding task due to high elution temperatures. However, the atropisomers of one tri-ortho substituted PBB congener (PBB 149) could be resolved on a column coated with randomly modified heptakis(6-O-tert.-butyldimethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin in OV 1701. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:123 / 133
页数:11
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