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A Catalytic Strategy for Selective Production of 5-Formylfuran-2-carboxylic Acid and Furan-2,5-dicarboxylic Acid

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Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/88653

Title: A Catalytic Strategy for Selective Production of 5-Formylfuran-2-carboxylic Acid and Furan-2,5-dicarboxylic Acid
Authors: Wiesfeld, Jan J. Browse this author
Asakawa, Miyuki Browse this author
Aoshima, Takayuki Browse this author
Fukuoka, Atsushi Browse this author →KAKEN DB
Hensen, Emiel J. M. Browse this author
Nakajima, Kiyotaka Browse this author →KAKEN DB
Keywords: biomass
FDCA
heterogeneous catalysis
HMF
protection strategy
Issue Date: 28-Mar-2022
Publisher: Wiley-Blackwell
Journal Title: ChemCatChem
Volume: 14
Issue: 16
Start Page: e202200191
Publisher DOI: 10.1002/cctc.202200191
Abstract: A novel catalytic strategy involving protective chemistry is presented for the selective production of 5-formylfuran-2-carboxylic acid (FFCA) and furan-2,5-dicarboxylic acid (FDCA) from concentrated 5-hydroxymethylfurfural (HMF) solutions. By protecting the reactive formyl group of HMF by acetalization with 1,3-propanediol (PDO), degradation and premature oxidation of HMF is suppressed. A hydroxyapatite-supported Au catalyst can selectively oxidize HMF-acetal in a 10 wt % solution to FFCA-acetal in 94 % yield in 2 hours at 373 K under 0.5 MPa of O-2. Deprotection of FFCA-acetal by mineral acids affords FFCA in 98 % yield and recovers nearly all PDO. FFCA in a 20 wt % solution can be oxidized to FDCA in 95 % yield under similar reaction conditions. The presented chemistry contributes to the development of novel manufacturing routes of prospective biobased monomer precursors using protecting agents.
Rights: This is the peer reviewed version of the following article: [J. J. Wiesfeld, M. Asakawa, T. Aoshima, A. Fukuoka, E. J. M. Hensen, K. Nakajima, ChemCatChem 2022, 14, e202200191.], which has been published in final form at [Link to final article using the DOI]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
Type: article (author version)
URI: http://hdl.handle.net/2115/88653
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 中島 清隆

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