Polycarboxylated compounds and compositions containing same

Patent · 02 July 2019

OSTI ID:1568544

Stahl, Shannon S.; Rafiee, Mohammad

Methods of selectively modifying lignin, polycarboxylated products thereof, and methods of deriving aromatic compounds therefrom. The methods comprise electrochemically oxidizing lignin using stable nitroxyl radicals to selectively oxidize primary hydroxyls on .beta.-O-4 phenylpropanoid units to corresponding carboxylic acids while leaving the secondary hydroxyls unchanged. The oxidation results in polycarboxylated lignin in the form of a polymeric .beta.-hydroxy acid. The polymeric .beta.-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The .beta.-hydroxy acid, anion, or salt can also be subjected to acidolysis to generate various aromatic monomers or oligomers. The initial oxidation of lignin to the polycarboxylated form renders the lignin more susceptible to acidolysis and thereby enhances the yield of aromatic monomers and oligomers obtained through acidolysis.

• Research Organization: Wisconsin Alumni Research Foundation, Madison, WI (United States)
• Sponsoring Organization: USDOE
• DOE Contract Number: FC02-07ER64494
• Assignee: Wisconsin Alumni Research Foundation (Madison, WI)
• Patent Number(s): 10,336,868
• Application Number: 15/167,103
• OSTI ID: 1568544
• Country of Publication: United States
• Language: English