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US 9,108,979 B2Granted
Diels-Alder reactions catalyzed by Lewis acid containing solids: renewable production of bio-plastics
AssigneeCalifornia Institute of Technology
InventorsMark E. Davis, Joshua Pacheco
Life of this patent
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Abstract
The present disclosure is related to silica-based Lewis acid catalysts, being essentially devoid of strong Brønsted acid character, and their ability to effect the [4+2] cycloaddition and dehydrative aromatization of dienes and dienophiles containing oxygenated substituents to form substituted benzene products. In some embodiments, the processes comprise contacting biomass-derived substrates with ethylene to form terephthalic acid and its derivatives.
Claims35
A process comprising contacting a compound of Formula (1):
- with a compound of Formula (2):
- in a non-aqueous solvent in the presence of a solid, silica-based Lewis acid catalyst that is essentially devoid of strong Brønsted acid character;
- under conditions sufficient to produce a compound of Formula (3) or Formula (4) or both:
- wherein R1 and R2 are each independently H, alkyl, or an oxygenated functional group, wherein at least one of R1 or R2 is the oxygenated functional group;
- wherein R3 is H, alkyl, or an oxygenated functional group;
- wherein said oxygenated functional group is an acetal, aldehyde, protected aldehyde, acyl, protected acyl, hydroxycarbonyl, alkoxycarbonyl, hydroxymethyl or alkoxymethyl.
3 more elements
Dependencies are inferred from the claim text.