Renewable Alternatives to Petroleum-Derived Products: Novel Approach Creates Nylon-12 and -13 Precursors from Lipids
Project ID: D2014-06Invention Description: Invention relates to a new olefin cross-metathesis approach for making C12 and C13 amino esters from oleic acid (or alkyl esters) originating from lipids. The method allows direct conversion of the widely abundant natural fatty acid oleic acid into synthetic precursors or nylon-12 and nylon-13 in half the steps than previously developed methods. Applications: Applications include automotive, transportation, sports, medical, high-performance cables, electronics, electrical compounds, photovoltaic panels, and even lenses for glasses. Novelty: Efficient two-step process for synthesizing nylon-12 and nylon-13 polymer units from unsaturated fatty acids including lipid-rich algae, oleic acid or any oil that has omega-9 fatty acids as a main component. Nylon-11, -12 and -13 are produced from amino acids (or their derivatives) which until development of this new process have only been derived from petrochemical or oleochemical resources by chemical synthesis. Value proposition: Advantages over existing strategies provide for the production of bioplastics at competitive prices and include: Simple two-step process: cross-metathesis and hydrogenation as opposed to 5-6 steps in currently available chemical synthesis Low temperature process provides exceptional conversion and selectivity. Any active catalyst may be used however, preferable catalyst has been identified. Use of renewable resources such as those that use natural fatty acids and esters from plant-derived biomass creates environmentally friendly product. Cross-metathesis produces fewer undesired by-products and hazardous wastes than chemical synthesis. Mild cross-metathesis conditions create neither disproportionation reaction nor transfer of carbon chain to other molecule across C=C bonds. Feedstock is readily available and non-toxic as compared to castor oil which contains ricin. Reduced to practice and ready for scale-up by industry partner/licensee.
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