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Title: Electrocatalytic hydrogenation of muconic acid

Abstract

Various embodiments disclosed relate to electrocatalytic hydrogenation of muconic acid and polymers formed from the reaction products thereof. In various embodiments, the present invention provides an electrocatalytic method to prepare 3-hexene-1,6-dioic acid, 2-hexene-1,6-dioic acid, adipic acid, or a combination thereof, from muconic acid. The method includes passing current through a catalytic cathode in a reactor including an aqueous acidic solution including muconic acid, a supporting electrolyte, and an anode, so as to generate atomic hydrogen on the cathode surface in an amount effective to hydrogenate the muconic acid to yield a product including 3-hexene-1,6-dioic acid, 2-hexene-1,6-dioic acid, adipic acid, or a mixture thereof. Also disclosed is the polymerization of 3-hexene-1,6-dioic acid, 2-hexene-1,6-dioic acid, or a combination thereof with another compound, such as a diamine or a dialcohol, to form a polymer, such as a polyamide or a polyester.

Inventors:
; ; ;
Issue Date:
Research Org.:
Ames Lab., Ames, IA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1650819
Patent Number(s):
10633750
Application Number:
15/524,888
Assignee:
Iowa States University Research Foundation, Inc. (Ames, IA)
Patent Classifications (CPCs):
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08G - MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
DOE Contract Number:  
AC02-07CH11358
Resource Type:
Patent
Resource Relation:
Patent File Date: 11/10/2015
Country of Publication:
United States
Language:
English

Citation Formats

Tessonnier, Jean-Philippe, Matthiesen, John Edward, Hernandez-Cantu, Nacu B., and Cochran, Eric W.. Electrocatalytic hydrogenation of muconic acid. United States: N. p., 2020. Web.
Tessonnier, Jean-Philippe, Matthiesen, John Edward, Hernandez-Cantu, Nacu B., & Cochran, Eric W.. Electrocatalytic hydrogenation of muconic acid. United States.
Tessonnier, Jean-Philippe, Matthiesen, John Edward, Hernandez-Cantu, Nacu B., and Cochran, Eric W.. Tue . "Electrocatalytic hydrogenation of muconic acid". United States. https://www.osti.gov/servlets/purl/1650819.
@article{osti_1650819,
title = {Electrocatalytic hydrogenation of muconic acid},
author = {Tessonnier, Jean-Philippe and Matthiesen, John Edward and Hernandez-Cantu, Nacu B. and Cochran, Eric W.},
abstractNote = {Various embodiments disclosed relate to electrocatalytic hydrogenation of muconic acid and polymers formed from the reaction products thereof. In various embodiments, the present invention provides an electrocatalytic method to prepare 3-hexene-1,6-dioic acid, 2-hexene-1,6-dioic acid, adipic acid, or a combination thereof, from muconic acid. The method includes passing current through a catalytic cathode in a reactor including an aqueous acidic solution including muconic acid, a supporting electrolyte, and an anode, so as to generate atomic hydrogen on the cathode surface in an amount effective to hydrogenate the muconic acid to yield a product including 3-hexene-1,6-dioic acid, 2-hexene-1,6-dioic acid, adipic acid, or a mixture thereof. Also disclosed is the polymerization of 3-hexene-1,6-dioic acid, 2-hexene-1,6-dioic acid, or a combination thereof with another compound, such as a diamine or a dialcohol, to form a polymer, such as a polyamide or a polyester.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2020},
month = {4}
}

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