Ring-Closing Metathesis Creates Nylon-11, -12 and -13 Precursors from Widely Abundant Plant-Derived Biomass


Project ID: D2014-39

IP Status: Provisional patent #62/020,488 filed

Invention Description: Invention relates to a new ring-closing-metathesis approach for making C11, C12 and C13 lactams (cyclic form of amino acids) 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 of nylon-11, -12 and -13 in fewer 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 three-step process for synthesizing nylon-11, -12 and -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 precursor has been prepared from oleochemical resources in as few as 3 steps.  However, nylon-12 precursor has historically required 5–6 steps from either petrochemical or oleochemical resources—never from biomass.

Value proposition: Advantages over existing strategies provide for the production of bioplastics at competitive prices and include:

·       Direct conversion of oleic acid into synthetic precursors of nylon-11, -12 and -13

·       Simple three-step process: 1) prepare amides, 2) ring-closing metathesis, 3) low-pressure hydrogenation vs. high pressure. Currently available chemical synthesis requires five or more steps.

·       Low temperature process provides exceptional conversion and selectivity.

·       Cost efficient--any active catalyst may be used, although preferred catalyst has been identified.

·       Use of renewable resources from plant-derived biomass is more environmentally friendly.

·       Ring-closing metathesis produces fewer undesired by-products and hazardous wastes than chemical syntheses methods.

·       Feedstock is readily available and non-toxic as compared to castor oil which contains toxic ricin.

·       Reduced to practice and ready for scale-up by industry partner/licensee.


Patent Information:
For Information, Contact:
Katherine Pollard
Licensing Associate
The University of Toledo
Sridhar Viamajala
Kana Yamamoto
Sasidhar Varanasi
Ajith Yapamudiyanselage