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

Gilkey, Matthew J.; Mironenko, Alexander V.; Vlachos, Dionisios G.; Xu, Bingjun

doi:10.1021/acscatal.7b01753

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

Journal Article · Wed Aug 16 00:00:00 EDT 2017 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.7b01753· OSTI ID:1469939

Gilkey, Matthew J. ^[1]; Mironenko, Alexander V. ^[1]; Vlachos, Dionisios G. ^[1];

^[1]

Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation, Dept. of Chemical & Biomolecular Engineering

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.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001004

OSTI ID:: 1469939

Journal Information:: ACS Catalysis, Vol. 7, 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; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 51 works

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

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