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The Use of Canola Oil as a Carbon Feedstock in the Synthesis of Value

  • Author / Creator
    Brown, Brenna Arlyce
  • With the increased strain on the world’s petroleum supplies, research efforts are turning toward establishing renewable sources of carbon in the generation of materials that are essential for consumer products ranging from pharmaceuticals to polymers. Canola oil is one such renewable resource that can be used as a carbon source. Transesterification of canola oil results in the liberation of unsaturated fatty acid methyl esters. Chemical manipulation of these unsaturated methyl esters can lead to more diverse chemical functionalities that would be useful in the preparation of value-added materials. Alkynes are one such functional group that can be used in the synthesis of more complex molecules. One special type of alkyne is benzyne. Benzyne can undergo cycloaddition reactions that can result in aromatic hydrocarbon scaffolds. This thesis will focus on the synthesis of terminal alkynes from canola oil, featuring a novel tandem ozonolysis-dibromoolefination reaction. The terminal alkynes will be used to synthesise aromatic rings through a [2+2+2] cycloaddition reaction. Alkyl-sustituted aromatic rings will be used as model compounds to the aromatic rings synthesised from canola oil. The synthesis of benzyne from these aromatic rings will be explored.

  • Subjects / Keywords
  • Graduation date
    2013-11
  • Type of Item
    Thesis
  • Degree
    Doctor of Philosophy
  • DOI
    https://doi.org/10.7939/R3707WX0J
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Doctoral
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Veinot, Jonathan G. C. (Chemistry)
  • Examining committee members and their departments
    • Curtis, Jonathan (Agriculture, Food and Nutritional Science)
    • West, Frederick G. (Chemistry)
    • Schlaf, Marcel (Chemistry, University of Guelph)
    • Lowary, Todd (Chemistry)
    • Bergens, Steven (Chemistry)