Polycarboxylated compounds and compositions containing same
Abstract
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 β-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 β-hydroxy acid. The polymeric β-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The β-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.
- Inventors:
- Issue Date:
- Research Org.:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1824043
- Patent Number(s):
- 11028235
- Application Number:
- 16/415,522
- Assignee:
- Wisconsin Alumni Research Foundation (Madison, WI)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08H - DERIVATIVES OF NATURAL MACROMOLECULAR COMPOUNDS
- DOE Contract Number:
- FC02-07ER64494
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 05/17/2019
- Country of Publication:
- United States
- Language:
- English
Citation Formats
Stahl, Shannon S., and Rafiee, Mohammad. Polycarboxylated compounds and compositions containing same. United States: N. p., 2021.
Web.
Stahl, Shannon S., & Rafiee, Mohammad. Polycarboxylated compounds and compositions containing same. United States.
Stahl, Shannon S., and Rafiee, Mohammad. Tue .
"Polycarboxylated compounds and compositions containing same". United States. https://www.osti.gov/servlets/purl/1824043.
@article{osti_1824043,
title = {Polycarboxylated compounds and compositions containing same},
author = {Stahl, Shannon S. and Rafiee, Mohammad},
abstractNote = {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 β-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 β-hydroxy acid. The polymeric β-hydroxy acid has a high loading of carboxylic acid and can be isolated in acid form, deprotonated, and/or converted to a salt. The β-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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2021},
month = {6}
}
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