Identification of brominated organic compounds in aquatic biota and exploration of bromine isotope analysis for source apportionment

........................................................................... 5 Table of contents ................................................................ 6 Abbreviations ..................................................................... 8 List of papers ..................................................................... 9 Statement ....................................................................... 10 Thesis objectives .............................................................. 11 1. Brominated organic compounds in the marine environment 13 1.1 Naturally produced brominated organic compounds ............................................................................ 13 1.2 Natural production of brominated organic compounds ............................................................................ 17 2. Bromine isotopes .......................................................... 20 2.1 Kinetic isotope effect ......................................... 20 2.2 Isotope fractionation processes ........................... 20 3. Samples and purification methods .................................. 23 3.1 Samples .......................................................... 23 3.2 Extraction and lipid removal methods .................. 24 3.3 Chromatographic separation ............................... 27 4. Analysis ....................................................................... 29 4.1 GC-MS ............................................................. 29 4.2 NMR ................................................................ 30 4.3 GC-multiple-collector-ICP-MS ............................. 31 5. Summary of papers....................................................... 33 5.1 Paper I Identification and quantification of PBDDs and Br/Cl-DDs ........................................................ 33 5.2 Paper II NMR-identification of a novel brominated organic compound isolated from whale blubber .......... 34 5.3 Paper III Development of a GC-MC-ICP-MS method for brominated diaromatic compounds ...................... 34 5.4 Paper IV Measurements of δBr in anthropogenic and natural monoaromatic compounds ...................... 35