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Permanent link (DOI): https://doi.org/10.7939/R3707WX0J

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

Descriptions

Other title
Subject/Keyword
Benzyne
Canola Oil
Fluorenone
Ozonolysis
Dibromoolefinatin
Alkynes
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Brown, Brenna Arlyce
Supervisor and department
Veinot, Jonathan G. C. (Chemistry)
Examining committee member and department
West, Frederick G. (Chemistry)
Bergens, Steven (Chemistry)
Lowary, Todd (Chemistry)
Curtis, Jonathan (Agriculture, Food and Nutritional Science)
Schlaf, Marcel (Chemistry, University of Guelph)
Department
Department of Chemistry
Specialization

Date accepted
2013-09-27T21:21:50Z
Graduation date
2013-11
Degree
Doctor of Philosophy
Degree level
Doctoral
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.
Language
English
DOI
doi:10.7939/R3707WX0J
Rights
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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File title: Microsoft Word - Abstract.doc
File author: Brenna Brown
Page count: 165
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