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Selective hydrogenation of 5-hydroxymethylfurfural and its acetal with 1,3-propanediol to 2,5-bis(hydroxymethyl)furan using supported rhenium-promoted nickel catalysts in water
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| Title: | Selective hydrogenation of 5-hydroxymethylfurfural and its acetal with 1,3-propanediol to 2,5-bis(hydroxymethyl)furan using supported rhenium-promoted nickel catalysts in water |
| Authors: | Wiesfeld, Jan J. Browse this author | | Kim, Minjune Browse this author | | Nakajima, Kiyotaka Browse this author →KAKEN DB | | Hensen, Emiel J. M. Browse this author |
| Issue Date: | 21-Feb-2020 |
| Publisher: | Royal Society of Chemistry |
| Journal Title: | Green chemistry |
| Volume: | 22 |
| Issue: | 4 |
| Start Page: | 1229 |
| End Page: | 1238 |
| Publisher DOI: | 10.1039/c9gc03856f |
| Abstract: | The high reactivity of the formyl group of 5-hydroxymethylfurfural (5-HMF) is problematic, because it leads to undesired oligomerization reactions. This is usually countered by working in dilute non-aqueous solutions. Here, we present a novel approach to convert concentrated aqueous solutions of 5-HMF to 2,5-bishydroxymethylfuran (BHMF), which is a prospective monomer for polyesters and self-healing polymers. Our approach is based on the protection of the formyl group of 5-HMF using acetalization with 1,3-propanediol. Hydrogenation is carried out using an optimized bimetallic Ni-Re catalyst supported on TiO2 at a carefully controlled pH, resulting in balanced rates of deprotection and hydrogenation and high BHMF yield. Under optimized conditions at a benign temperature of 40 degrees C, hydrogenation of concentrated solutions (10-20 wt%) of protected 5-HMF in water gave 81-89% yields of BHMF without having to resort to platinum-group metals such as palladium or platinum. |
| Rights: | © 2020 The Royal Society of Chemistry | | https://creativecommons.org/licenses/by/4.0/ |
| Type: | article |
| URI: | http://hdl.handle.net/2115/78704 |
| 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)
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