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Novel Strategies for the Safe Chemical Degradation of Organic Peroxide Explosives: a Mechanistic Investigation

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Novel Strategies for the Safe Chemical Degradation of Organic Peroxide Explosives: a Mechanistic Investigation Novel strategies for the safe chemical degradation of organic peroxide explosives: A mechanistic investigation Mark Stephen Bali Captain, Australian Army A thesis in fulfilment of the requirements for the degree of Doctor of Philosophy School of Physical, Environmental and Mathematical Sciences The University College, UNSW Canberra November 2014 i “The nation that will insist on drawing a broad line of demarcation between the fighting man and the thinking man is liable to find its fighting done by fools and its thinking done by cowards.” Sir William Francis Butler ii iii Table of Contents CHAPTER 1. Introduction ........................................................................................ 1 1.1 Terrorism and explosives ................................................................................... 1 1.2 Organic Peroxides .............................................................................................. 3 1.2.1 Organic peroxides as explosives ........................................................................... 4 1.2.2 Organic peroxide incidents ................................................................................... 8 1.2.3 Unique Hazards ..................................................................................................... 9 1.2.4 Neutralising peroxide explosives ........................................................................ 12 1.3 The chemistry of TATP – A literature review.................................................. 12 1.3.1 Acidic Degradation ............................................................................................. 13 1.3.2 Thermolysis ......................................................................................................... 18 1.3.3 Metals and metal ions ......................................................................................... 20 1.3.4 Other reactions .................................................................................................... 22 1.3.5 Theoretical possiblities ....................................................................................... 24 1.4 Other peroxide chemistry of relevance............................................................. 24 1.4.1 Baeyer-Villiger reactions .................................................................................... 24 1.4.2 Redox and electrochemistry of cyclic peroxides ................................................ 27 1.4.3 Lewis acid reactions with organic peroxides. ..................................................... 27 1.5 Related peroxides ............................................................................................. 28 1.6 Conclusion ........................................................................................................ 32 1.7 This Study ......................................................................................................... 35 1.8 References ........................................................................................................ 36 CHAPTER 2. Tripentanone triperoxide as a model for TATP degradation studies 41 2.1 Introduction ...................................................................................................... 41 2.2 Research Goals ................................................................................................. 42 iv 2.3 Experimental .................................................................................................... 43 2.3.1 Instruments .......................................................................................................... 43 2.3.2 Sensitiveness testing ........................................................................................... 45 2.3.3 Synthesis ............................................................................................................. 45 2.3.4 Acid degradation studies ..................................................................................... 47 2.3.5 Thermal degradation studies ............................................................................... 47 2.3.6 Explosive Detection Dog field trial .................................................................... 47 2.4 Results .............................................................................................................. 49 2.4.1 Pentanone peroxides and their characterisation .................................................. 49 2.4.2 Relative Safety .................................................................................................... 54 2.4.3 Acidic Degradation ............................................................................................. 56 2.4.4 Thermal Degradation .......................................................................................... 60 2.4.5 Scent characteristics ............................................................................................ 61 2.5 Conclusion ........................................................................................................ 65 2.6 Acknowledgements .......................................................................................... 66 2.7 References ........................................................................................................ 66 CHAPTER 3. Redox and electrochemistry of cyclic peroxides ........................... 69 3.1 Introduction ...................................................................................................... 69 3.2 Research Goals ................................................................................................. 70 3.3 Experimental .................................................................................................... 70 3.3.1 Materials ............................................................................................................. 70 3.3.2 Instruments .......................................................................................................... 71 3.3.3 Redox degradation studies .................................................................................. 72 3.3.4 Electrochemistry ................................................................................................. 72 3.4 Results and Discussion ..................................................................................... 73 3.4.1 Redox reactions ................................................................................................... 73 3.4.2 Electrochemistry ................................................................................................. 76 3.5 Conclusion ........................................................................................................ 79 v 3.6 References ........................................................................................................ 81 CHAPTER 4. The reaction of metal-based Lewis acids with TPTP ................... 82 4.1 Introduction ...................................................................................................... 82 4.2 Research Goals ................................................................................................. 84 4.3 Experimental .................................................................................................... 84 4.3.1 Materials ............................................................................................................. 84 4.3.2 Instruments .......................................................................................................... 85 4.3.3 Methods ............................................................................................................... 86 4.3.3.1 Preparation and determination of TiCl4 stock solution .............................. 86 4.3.3.2 TPTP-TiCl4 degradation experiments ......................................................... 86 4.3.3.3 Preparation and determination of TiCl4L2 stock solutions ......................... 90 4.3.3.4 Degradation of TPTP by TiCl4L2 ................................................................ 90 4.3.3.5 Degradation of TPTP by SbCl3 ................................................................... 91 4.4 Results and discussion ...................................................................................... 92 4.4.1 Titanium tetrachloride ......................................................................................... 92 4.4.1.1 The reaction of TPTP with a large excess of TiCl4 ..................................... 92 4.4.1.2 1:0.5 reaction of TPTP with TiCl4 .............................................................. 93 4.4.1.3 Characterisation of solid product from Ti-limited reactions .................... 100 4.4.1.4 IR Studies .................................................................................................. 103 4.4.1.5 The effect of reagent ratio ......................................................................... 108 4.4.1.6 The effect of ligands .................................................................................. 114 4.4.1.7 Diffusion effects ......................................................................................... 119 4.4.1.8 Inter- vs. Intra-molecular rearrangement ................................................. 120 4.4.2 Proposed Mechanism ........................................................................................ 121 4.4.3 Antimony trichloride ......................................................................................... 127 4.5 Conclusion
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