A study of ozonolysis reactions for lipid transformations by mass spectrometry

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Ozonolysis involves the reaction of ozone with unsaturated organic compounds. It has been used as a method to determine double bond positions in natural products and lipids for more than half a century. Recently, the ozonolysis of lipids has been combined with electrospray mass spectrometry, thereby allowing direct observation of the ozonolysis products. Ozonolysis is also being developed as part of a process to convert the unsaturated fatty acids present in vegetable oils into compounds known as "polyols" which are used in the manufacture of polyurethanes. Polyols produced from renewable resources, such as canola oil, could replace some of the millions of tonnes of polyols produced by the petrochemical industry for making a wide range of materials including rigid and elastic foams, coatings, adhesives and plastics. This Discovery program is a fundamental study of the ozonolysis of natural oils and fats. Ozonolysis will be performed in laboratory and pilot scale reactors, as well as in situ in a mass spectrometer ion source in order to monitor the ozonolysis intermediates and their further reactions. Enhanced understanding of the ozonolysis of commodity lipids and the products which can be obtained from them will provide direction for new bio-polyol development, an exciting prospect with enormous potential for Canadian farmers and chemical manufacturers. An additional objective of this program is to further develop the analytical potential of ozonolysis/mass spectrometry for lipid applications of importance in health, agriculture and nutrition.