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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 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}
}

Works referenced in this record:

Electrochemical treatment of lignins
patent, November 1988


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


Hydroxy Acid Complexes for Skin Antiaging, Acne, and Skin Whitening
patent-application, October 2013


Method for Producing Vanillin by Electrochemical Oxidation of Aqueous Lignin Solutions or Suspensions
patent-application, February 2013


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


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


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