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

Abstract

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.