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Effective Oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran by an Acetal Protection Strategy

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Title: Effective Oxidation of 5-Hydroxymethylfurfural to 2,5-Diformylfuran by an Acetal Protection Strategy
Authors: Boonyakarn, Tat Browse this author
Wiesfeld, Jan J. Browse this author
Asakawa, Miyuki Browse this author
Chen, Lulu 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: 5-hydroxymethylfurfural
heterogeneous catalysis
Issue Date: 7-Apr-2022
Publisher: Wiley-Blackwell
Journal Title: ChemSusChem
Volume: 15
Issue: 7
Start Page: e202200059
Publisher DOI: 10.1002/cssc.202200059
Abstract: An acetal protection strategy for 5-hydroxymethylfurfural (HMF) was used to obtain 2,5-diformyfuran (DFF) using concentrated HMF solutions and a gamma-Al2O3-supported Ru catalyst (Ru/gamma-Al2O3). The HMF-acetal with 1,3-propanediol can be oxidized to DFF-acetal with a yield of 84.0 % at an HMF conversion of 94.2 % from a 50 wt % solution. In contrast, aerobic oxidation of nonprotected HMF using a 10 wt % solution afforded DFF only in a moderate yield (52.3 %). Kinetic studies indicated that the six-membered ring acetal group not only prevents side reactions but also accelerates aerobic oxidation of the -CH2OH moiety to -CHO under retention of the acetal functionality. Organic deposits formed during the reaction explained the significant decrease in the activity of the Ru/gamma-Al2O3 catalyst, which could be recovered neither by washing in water or organic solvents, nor by a calcination-reduction treatment. Sonication of the used Ru/gamma-Al2O3 catalyst in an aqueous NaOH solution successfully removed the deposits and allowed reuse of the catalyst for at least four times without activity loss.
Rights: This is the peer reviewed version of the following article: [T. Boonyakarn, J. J. Wiesfeld, M. Asakawa, L. Chen, A. Fukuoka, E. J. M. Hensen, K. Nakajima, ChemSusChem 2022, 15, e202200059.], which has been published in final form at []. 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)
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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