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Title: Adipic Acid Production via Metal-Free Selective Hydrogenolysis of Biomass-Derived Tetrahydrofuran-2,5-Dicarboxylic Acid

Abstract

Biomass-derived furans offer sustainable routes to adipic acid (AA), a key chemical in Nylon-6,6 synthesis. In this work, we show that tetrahydrofuran-2,5-dicarboxylic acid (THFDCA) is a viable precursor for AA production, achieving up to 89% yield in a metal-free system containing HI and molecular H2 in a propionic acid solvent at 160 °C. Reactivity studies demonstrate that the interplay between HI, H2, and the solvent is essential for effective THFDCA ring opening. By measuring the reaction orders of HI and molecular H2 and calculating an acid–base equilibrium constant in a nonaqueous solvent, we show that HI plays a multifaceted role in the reaction by acting both as a proton source and an iodide source to selectively cleave C–O bonds without overhydrogenation of carboxylic acid groups. Using reactivity studies, kinetic measurements, and first-principles computational insights, we demonstrate that metal-free activation of molecular H2 plays a key role in the reaction, following HI-mediated cleavage of the etheric C–O bond in THFDCA.

Authors:
 [1];  [1];  [1]; ORCiD logo [1]
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  1. Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation, Dept. of Chemical & Biomolecular Engineering
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1469939
Grant/Contract Number:  
SC0001004
Resource Type:
Accepted Manuscript
Journal Name:
ACS Catalysis
Additional Journal Information:
Journal Volume: 7; Journal Issue: 10; Related Information: CCEI partners with the University of Delaware (lead); Brookhaven National Laboratory; California Institute of Technology; Columbia University; University of Delaware; Lehigh University; University of Massachusetts, Amherst; Massachusetts Institute of Technology; University of Minnesota; Pacific Northwest National Laboratory; University of Pennsylvania; Princeton University; Rutgers University; Journal ID: ISSN 2155-5435
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous); catalysis (heterogeneous); biofuels (including algae and biomass); bio-inspired; hydrogen and fuel cells; materials and chemistry by design; synthesis (novel materials); synthesis (self-assembly); synthesis (scalable processing)

Citation Formats

Gilkey, Matthew J., Mironenko, Alexander V., Vlachos, Dionisios G., and Xu, Bingjun. Adipic Acid Production via Metal-Free Selective Hydrogenolysis of Biomass-Derived Tetrahydrofuran-2,5-Dicarboxylic Acid. United States: N. p., 2017. Web. doi:10.1021/acscatal.7b01753.
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Gilkey, Matthew J., Mironenko, Alexander V., Vlachos, Dionisios G., & Xu, Bingjun. Adipic Acid Production via Metal-Free Selective Hydrogenolysis of Biomass-Derived Tetrahydrofuran-2,5-Dicarboxylic Acid. United States. https://doi.org/10.1021/acscatal.7b01753
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Gilkey, Matthew J., Mironenko, Alexander V., Vlachos, Dionisios G., and Xu, Bingjun. Wed . "Adipic Acid Production via Metal-Free Selective Hydrogenolysis of Biomass-Derived Tetrahydrofuran-2,5-Dicarboxylic Acid". United States. https://doi.org/10.1021/acscatal.7b01753. https://www.osti.gov/servlets/purl/1469939.
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@article{osti_1469939,
title = {Adipic Acid Production via Metal-Free Selective Hydrogenolysis of Biomass-Derived Tetrahydrofuran-2,5-Dicarboxylic Acid},
author = {Gilkey, Matthew J. and Mironenko, Alexander V. and Vlachos, Dionisios G. and Xu, Bingjun},
abstractNote = {Biomass-derived furans offer sustainable routes to adipic acid (AA), a key chemical in Nylon-6,6 synthesis. In this work, we show that tetrahydrofuran-2,5-dicarboxylic acid (THFDCA) is a viable precursor for AA production, achieving up to 89% yield in a metal-free system containing HI and molecular H2 in a propionic acid solvent at 160 °C. Reactivity studies demonstrate that the interplay between HI, H2, and the solvent is essential for effective THFDCA ring opening. By measuring the reaction orders of HI and molecular H2 and calculating an acid–base equilibrium constant in a nonaqueous solvent, we show that HI plays a multifaceted role in the reaction by acting both as a proton source and an iodide source to selectively cleave C–O bonds without overhydrogenation of carboxylic acid groups. Using reactivity studies, kinetic measurements, and first-principles computational insights, we demonstrate that metal-free activation of molecular H2 plays a key role in the reaction, following HI-mediated cleavage of the etheric C–O bond in THFDCA.},
doi = {10.1021/acscatal.7b01753},
journal = {ACS Catalysis},
number = 10,
volume = 7,
place = {United States},
year = {Wed Aug 16 00:00:00 EDT 2017},
month = {Wed Aug 16 00:00:00 EDT 2017}
}
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https://doi.org/10.1021/acscatal.7b01753
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