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Title: 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 .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.

Inventors:
;
Issue Date:
Research Org.:
Wisconsin Alumni Research Foundation, Madison, WI (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1568544
Patent Number(s):
10,336,868
Application Number:
15/167,103
Assignee:
Wisconsin Alumni Research Foundation (Madison, WI)
DOE Contract Number:  
FC02-07ER64494
Resource Type:
Patent
Resource Relation:
Patent File Date: 05/27/2016
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., 2019. 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/1568544.
@article{osti_1568544,
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 .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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2019},
month = {7}
}

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Works referenced in this record:

Cinnamic acid-based oligomers and uses thereof
patent, July 2013


Poly(hydroxy acid)/polymer conjugates for skin applications
patent, July 2001


Method of using beta hydroxy acids for treating wrinkles
patent, March 1999


Nitroxyl-mediated oxidation of lignin and polycarboxylated products
patent, February 2018


Electrochemical treatment of lignins
patent, November 1988


Lignin by-products of paper-making process
patent, April 1988