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Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions

Paper ID Volume ID Publish Year Pages File Format Full-Text
40517 45857 2013 7 PDF Available
Title
Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions
Abstract

The renewable chemical building block 5-hydroxymethylfurfural (HMF) was oxidized to 2,5-diformylfuran by an oxidation system consisting of the radical 2,2,6,6-tetramethyl-piperidin-1-oxyl (TEMPO) and CuCl. The system was optimized by exploring several reaction conditions and by employing nitrogen containing promoters (NCPs) to obtain excellent yields. In acetonitrile a 95% DFF yield was obtained after 24 h with ambient pressure of dioxygen at room temperature in the presence of different NCPs, which – to our knowledge – is the best result reported thus far for this reaction. The use of NCPs made it further possible to apply various traditional solvents, e.g. acetone, methanol and methyl isobutyl ketone for the reaction. The latter can be used as extraction solvent for HMF synthesis in aqueous media and thus integrate the two processes. Additionally, HMF was oxidized to 2,5-furandicarboxylic acid by a modified oxidation protocol consisting of CuCl and t-BuOOH. In all the reactions, mild conditions, including room temperature were employed.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (125 K)Download as PowerPoint slideHighlights► Aerobic oxidation of HMF to DFF was performed at ambient conditions with CuCl/TEMPO. ► An optimized DFF yield of 95% was obtained with use of nitrogen containing promoters. ► HMF was oxidized directly to FDA by oxidation with CuCl/t-BuOOH catalyst.

Keywords
5-Hydroxymethylfurfural; Oxidation; Copper; Radical reactions; 2,5-Diformylfuran
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Cu catalyzed oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran and 2,5-furandicarboxylic acid under benign reaction conditions
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 456, 10 April 2013, Pages 44–50
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us