Metathesis-derived Green Lubricants, Waxes, Polymers and Chemicals from Vegetable Oils

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The proposed research is focused on the use of a green method, metathesis, to chemically modify vegetable oils to produce a range of environmentally friendly products: thermoplastic polymers, high value chemicals, functional lubricants and functional waxes. Metathesis is a process whereby the atoms connected to two carbon-carbon double bonds change places with one another.  This results in totally new chemicals being formed from unsaturated feedstock such a vegetable oils.  When metathesis is conducted with only a single feedstock, such as an unsaturated vegetable oil, the process is referred to as self-metathesis. This process results in the isomerization, cyclization and concatenation of the basic building block of a vegetable oil molecule, the triacylglyceride molecule.  If the starting feedstock and the processing conditions are controlled, the resulting product mixture can be structurally enhanced to deliver a range of functional properties, ranging from liquid lubricants to solid waxes with varying viscosities, melting temperatures, hardness and adhesion properties. The introduction of a small unsaturated molecule into the starting mixture for metathesis results in both self- and cross- metathesis taking place, and in the case of an unsaturated vegetable oil, this approach can be used to introduce functional groups into the self-metathesis products, further enhancing the physical properties of the final product mixture by increasing properties such as viscosity and adhesion.  In the case of polymers, cross-metathesis can be utilized so as to introduce a large amount of functional groups at specific locations on the basic building block of a vegetable oil; these functional groups then become the sites for the stitching together of the basic building blocks into long chain polymers.  Cross-metathesis also creates smaller by-product molecules, which are often very functional in their own right as high value platform chemicals.  This research focusses on the control of the starting materials and processing conditions to produce controlled structures in the final products of self-, cross- and simultaneous self-/cross- metathesis reactions of vegetable oils.  By studying the relationship of the structure of the products of metathesis to their physical functionality, the metathesis reaction can be targeted with judicious selection of the starting materials to produce highly functional polymers, chemicals, lubricants and waxes.  These materials are currently produced from petrochemicals from carbon-intensive petrochemical industries.  This research has the potential to switch the source of these ubiquitous materials from petroleum carbon to renewable, agriculturally grown carbon. Furthermore, the process used is green and not energy intensive and the products themselves environmentally friendly.  Utilization of renewable carbon in materials also helps abate climate change.**