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US 8,993,689 B1Granted
Polyphenols and high-performance resins from syringaldehyde
AssigneeThe United States of America as represented by the Secretary of the Navy
InventorsBenjamin G. Harvey, Matthew C. Davis, Heather A. Meylemans, William Lai
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Abstract
A method to generate renewable high performance composites and thermoplastics. These materials can be generated from a renewable phenol (syringaldehyde) that can be derived from lignocellulosic biomass. The use of syringaldehyde as a precursor to composites has the potential to reduce the cost and environmental impact of structural materials, while meeting or exceeding the performance of current petroleum derived resins.
Claims18
A method for making resins from syringaldehydes, comprising:
- reductively coupling syringaldehyde with an additional molecule of syringaldehyde or at least one aromatic aldehyde having a hydroxy group, and/or methoxy group in at least one position on said aldehyde by a McMurry reaction or by reductive chemical or electrochemical reaction to produce at least one first reductive coupling product;
- further reducing said first reductive coupling product by hydrogenation or chemical reduction or electrochemical reduction to produce a second reductive coupling product;
- deoxygenating and demethylating said second reductive product(s) by conversion to a sulfonate followed by reaction with a reductive elimination catalyst and further reaction with a hydrolyzing reagent to produce polyphenols;
- and
- converting said polyphenols by reaction with a soluble base and cyanogen halide(s) or pseudohalides to produce cyanate ester resin(s).
2 more elements
Dependencies are inferred from the claim text.