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Studies of the Nitration of Cellulose – Application in New Membrane Materials

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Studies of the Nitration of Cellulose – Application in New Membrane Materials STUDIES OF THE NITRATION OF CELLULOSE – APPLICATION IN NEW MEMBRANE MATERIALS by Clement Cheung B. Sc., University of British Columbia, 2011 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in The Faculty of Graduate and Postdoctoral Studies (Chemistry) THE UNIVERSITY OF BRITISH COLUMBIA (Vancouver) February 2014 ©Clement Cheung, 2014 Abstract Since the discovery of the production of nanocrystalline cellulose (NCC) from acid hydrolysis of bulk cellulose, this material has been used as a template for imparting photonic properties on materials without innate structural ordering and as an additive in polymer composites to increase structural strength. However, the potential of NCC as a feedstock for highly nitrated cellulose has not been investigated. It is postulated that the smaller chain lengths in NCC may permit a higher degree of nitration in comparison with conventional nitrocellulose. In this thesis, various nitration methods have been investigated for their ability to produce highly nitrated NCC. Traditional nitration methods using HNO3/H2SO4 and less common nitration methods using HNO3/P2O5 and HNO3/Ac2O were used and the differences between methods were studied. There was an effect in using H2SO4 as the desiccant on the hindrance of the degree of nitration. Titration of the nitrated material with base shows the presence of more sulfate groups in samples nitrated in the presence of H2SO4 than in the absence of it, demonstrating that H2SO4 is a less ideal desiccant. In addition, pretreatment of NCC with a desulfation procedure improved the degree of nitration. The investigation of the other desiccants showed the importance of using a miscible, non-degrading desiccant to obtain a high degree of nitration. The synthesized nitrated nanocrystalline cellulose, hereby abbreviated as NNC, were analyzed by elemental analysis for the nitrogen content, powder X-ray diffraction for crystallinity, Fourier-transform infrared spectroscopy and thermal gravimetric analysis for the stability of the compound. ii Preface All of the results presented in this thesis were obtained while I worked under the supervision of Professor Mark J. MacLachlan. All experiments in Chapter 2 and Chapter 3 were conducted by me. iii Table of Contents Abstract ........................................................................................................................................................ ii Preface ......................................................................................................................................................... iii Table of Contents ....................................................................................................................................... iv List of Tables .............................................................................................................................................. vi List of Figures ............................................................................................................................................ vii List of Symbols ........................................................................................................................................... xi List of Abbreviations ................................................................................................................................ xii Acknowledgements .................................................................................................................................. xiii Chapter 1 – Introduction ............................................................................................................................ 1 1.1 Modifications of cellulose ........................................................................................................... 1 1.2 History and uses of nitrocellulose .............................................................................................. 3 1.3 Methods of nitration of cellulose ................................................................................................ 8 1.4 Optimization, manufacturing and stability of nitrocellulose ................................................ 12 1.5 Choosing nanocrystalline cellulose .......................................................................................... 16 1.6 Overview of this thesis .............................................................................................................. 20 Chapter 2 – Methods of nitration of NCC .............................................................................................. 21 2.1 Introduction ..................................................................................................................................... 21 2.2 Experimental ................................................................................................................................... 22 Materials. ........................................................................................................................................... 22 Aqueous desulfation of NCC. ........................................................................................................... 22 Heterogeneous desulfation of NCC. ................................................................................................ 23 HNO3/H2SO4 method. ....................................................................................................................... 23 HNO3/P2O5 method. .......................................................................................................................... 24 HNO3/Ac2O method. ......................................................................................................................... 24 Characterization techniques. ........................................................................................................... 25 2.3 Results and discussion .................................................................................................................... 25 The need for desulfation. .................................................................................................................. 25 Optimization of HNO3/H2SO4 method. ........................................................................................... 31 Optimization of HNO3/P2O5 method. .............................................................................................. 41 Optimization of HNO3/Ac2O method. ............................................................................................. 51 iv Comparison of the NNC products. .................................................................................................. 61 2.4 Conclusion ....................................................................................................................................... 66 Chapter 3 – Stability studies of NNC ...................................................................................................... 67 3.1 Introduction ..................................................................................................................................... 67 3.2 Experimental conditions ................................................................................................................. 68 Characterization techniques. ........................................................................................................... 68 Stabilization of NNC. ........................................................................................................................ 68 3.3 Results and discussion .................................................................................................................... 68 Aqueous stabilization of NNC. ......................................................................................................... 68 Stability of NNC synthesized with different methods. ................................................................... 75 3.4 Conclusion ....................................................................................................................................... 81 Chapter 4 – Conclusions and final remarks ........................................................................................... 83 References .................................................................................................................................................. 85 v List of Tables Table 2-1 – %N comparisons of the effect of aqueous and methanolic desulfation of NCC. Results show the effectiveness of the latter method for achieving a higher degree of nitration. ...................................... 28 Table 2-2 – %N comparison of the effect of water on the nitration efficiency. The H2SO4 removes ~20% of the water in the reaction and has little effect when a more concentrated HNO3 is used. ....................... 34 Table 2-3 – Effect of the readdition of P2O5 into the nitration mixture in 0.5 g portions on %N in NNC. The lack of an effect demonstrates the initial amount of desiccant is sufficient in the removal of initial water content and also the water generated during the nitration. ................................................................ 48 Table 2-4 – %N obtained from EA showing difference and reproducibility between normal and scaled-up nitration reactions. The inability for HNO3 and P2O5 to quickly disperse NCC leads to the formation of aggregates of lesser nitrated material. ........................................................................................................
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