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5.1.2 Dioctyl Sodium Sulfosuccinate http://researchcommons.waikato.ac.nz/ Research Commons at the University of Waikato Copyright Statement: The digital copy of this thesis is protected by the Copyright Act 1994 (New Zealand). The thesis may be consulted by you, provided you comply with the provisions of the Act and the following conditions of use: Any use you make of these documents or images must be for research or private study purposes only, and you may not make them available to any other person. Authors control the copyright of their thesis. You will recognise the author’s right to be identified as the author of the thesis, and due acknowledgement will be made to the author where appropriate. You will obtain the author’s permission before publishing any material from the thesis. Development of a Method for Trace Analysis of Dioctyl Sodium Sulfosuccinate by Liquid Chromatography Mass Spectrometry and its Application to Samples from the MV Rena Incident A thesis submitted in partial fulfilment of the requirements for the degree of Master of Science (Research) in Chemistry at The University of Waikato by Daniel Richard Bernstein The University of Waikato 2015 Abstract The grounding of the MV Rena off the coast of Tauranga, New Zealand in 2011 prompted the application of Corexit® oil spill dispersants in an attempt to mitigate the impact of the spilled oil to coastal ecosystems. A quantitative method was developed employing sonication assisted extraction from beach sand followed by sample clean up by solid phase extraction and analysis by liquid chromatography tandem mass spectrometry for the analysis of Corexit® component dioctyl sodium sulfosuccinate (DOSS) at trace levels. The chromatographic method included the use of a C8 stationary phase with a gradient elution and quantitation by an internal standard approach based on mass spectrometer instrument response. Validation studies gave recoveries of 72 ± 1.7% with an accuracy of 94%. Calibration curves were shown to have a linear range of 0 – 200 μg.L-1. Application of the method to the available environmental samples showed no presence of DOSS. An attempt was made to apply the instrumental method to heavy fuel oil (HFO) tar-balls and oiled sand samples. Multiple extraction techniques were trialled including liquid-liquid extraction, sonication assisted extraction and anion exchange chromatography with recovery experiments for each method being carried out. Analysis of the extracts showed that quantitative recovery of DOSS had not been achieved for any of the methods investigated. The difficulties associated with extracting DOSS from HFO tar-balls and oil sands suggest that the application of DOSS to surface oil slicks results in the preferential partitioning of DOSS into HFO. This has implications with respect to the distribution of DOSS in the environment following application, subsequent environmental monitoring and the degradation of HFO components by microbial communities. i Acknowledgements Firstly, I would like to thank my supervisor Associate Professor Merilyn Manley- Harris for organizing the project and for the opportunity to undertake this work. Your knowledge and experience has been invaluable and I am grateful for the time you have made for me in reviewing this thesis. To my co-supervisor, Professor Chris Battershill, I am grateful for the opportunity and appreciate you providing and organizing the project. Thanks to Rex Fairweather from the Coastal Marine Field Station, for helping to supply sediments and track down the samples for analysis. At the University of Waikato, I would like to extend my thanks to our great technicians in the chemistry department; Annie Barker, Pat Gread, Jenny Stockdill, John Little and Tom Featonby for all their help and Wendy Jackson for my initial training on the LC-MS. Thanks also to Megan Grainger, John McDonald Wharry and Maria Revell for the useful insights and showing me around when I was starting out. Thanks to Stephen O’Neill at Z Energy Ltd, for generously providing HFO samples for the method development. Finally, a big thank you to my Mum and Dad for all their support and especially for their patience. Also, thanks to all of my family and friends who have been supportive throughout this time. ii Table of Contents Abstract ..................................................................................................................... i Acknowledgements .................................................................................................. ii Table of Contents .................................................................................................... iii List of Figures ......................................................................................................... vii List of Tables ............................................................................................................ xi List of Abbreviations ............................................................................................. xiv 1 Introduction ....................................................................................................... 1 1.1 Oil Dispersants .............................................................................................. 4 1.1.1 Surfactants ............................................................................................ 5 1.1.1.1 Types of surfactants .................................................................... 5 1.1.2 Components of Corexit® 9500 and Corexit® 9527 ................................ 7 1.1.2.1 Anionic components ................................................................. 10 1.1.2.2 Non-ionic components .............................................................. 10 1.1.2.3 Toxicity of Corexit® 9500 in the marine environment .............. 12 1.1.3 Degradation of surfactants in the environment ................................. 13 1.1.3.1 Degradation of dioctylsulfosuccinate ....................................... 13 1.1.3.2 Degradation of sorbitan ester surfactants ................................ 17 1.2 Analysis of surfactants in the environment ................................................ 18 1.2.1 Sampling .............................................................................................. 18 1.2.2 Sample Preparation ............................................................................. 18 1.2.2.1 Homogenization ........................................................................ 19 1.2.2.2 Extraction methods ................................................................... 19 1.2.3 Chromatographic Separation .............................................................. 24 1.2.4 Mass Spectrometric Detection ............................................................ 27 iii 1.2.4.1 Quantitative analysis by mass spectrometry ............................ 28 1.2.4.1.1 Internal standards ................................................................ 28 2 Development of the instrumental method ..................................................... 31 2.1 Direct infusion mass spectrometry ............................................................. 31 2.1.1 Direct infusion mass spectrometry of C9500 ...................................... 32 2.1.2 Direct infusion mass spectrometry of surfactant standards .............. 34 2.2 HPLC-MS ...................................................................................................... 37 2.2.1 HPLC .................................................................................................... 37 2.2.1.1 Stability of MS signal response ................................................. 38 2.2.1.2 Analytical standards .................................................................. 40 2.2.1.3 Internal standards ..................................................................... 41 2.2.1.4 Auto-sampler carryover ............................................................ 41 2.2.1.5 UV-DAD detection ..................................................................... 41 2.2.2 ESI-IT-MS ............................................................................................. 42 2.2.2.1 Eluent modifiers ........................................................................ 42 2.2.2.2 ESI source settings ..................................................................... 43 2.2.2.3 ESI-MS-MS transitions ............................................................... 44 2.2.2.4 Fragmentation amplitude ......................................................... 48 2.2.2.5 LC-MS-MS instrument calibration ............................................. 49 2.2.3 Validation ............................................................................................ 51 2.3 Final LC-MS-MS instrument parameters .................................................... 52 3 Application of the instrumental method to real and simulated samples ....... 53 3.1 Preparation of procedural blank sample matrices ..................................... 53 3.1.1 Beach sand procedural blank .............................................................. 53 3.1.2 HFO tar-ball procedural blank ............................................................. 54 3.1.3 Oiled sand procedural blank ............................................................... 55 iv 3.2 Extraction from beach sand ........................................................................ 55 3.2.1 Soxhlet extraction ............................................................................... 55 3.2.2 Sonication assisted extraction
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