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

  • Canola Oil
  • Alkynes
  • Fluorenone
  • Benzyne
  • Dibromoolefinatin
  • Ozonolysis

• Graduation date

  Fall 2013

• 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.