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Robust Amidation Transformation of Plant Oils into Fatty Derivatives for Sustainable Monomers and Polymers

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Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, United States
*(C.T.) E-mail: [email protected]
Cite this: Macromolecules 2015, 48, 5, 1320–1328
Publication Date (Web):February 25, 2015
Copyright © 2015 American Chemical Society

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    Sustainable fuels, chemicals, and materials from renewable resources have recently gained tremendous momentum in a global scale, although there are numerous nontrivial hurdles for making them more competitive with petroleum counterparts. We demonstrate a robust strategy for the transformation of plant oils into polymerizable monomers and thermoplastic polymer materials. Specifically, triglycerides were converted into N-hydroxyalkyl fatty amides with the aid of amino alcohols via a mild base-catalyzed amidation process with nearly quantitative yields without the use of column chromatography and organic solvents. These fatty amides were further converted into a variety of methacrylate monomers, cyclic norbornene monomers and imino ether monomers. Representative polymers from selected monomers exhibit drastic different physical properties with subtle structural variations, highlighting the potential of this particular amidation reaction in the field of biomass transformation.

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