2,5-Furandicarboxaldehyde (FDC) is an organic compound with the molecular formula C4H2O(CHO)2. It consists of a furan ring with aldehyde groups on the 2 and 5 position. It is therefore classified as a dialdehyde.
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| Names | |
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| Other names
Furan-2,5-dicarboxaldehyde,
2,5-Diformylfuran
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| Identifiers | |
3D model (JSmol)
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| Abbreviations | FDC |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.011.382 |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C6H4O3 | |
| Molar mass | 124.095 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P305+P351+P338 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
edit2,5-Furandicarboxaldehyde is an oxidation product of 5-hydroxymethyl furfural (HMF), which in turn can be prepared from fructose. Alternatively, methods have been developed to convert fructose in one step to 2,5-furandicarboxaldehyde.[1] The conversion from fructose to HMF and FDC can be performed relatively efficiently and following the principles of green chemistry. As such, these materials are often considered as "greener" bio-based alternatives.[citation needed]
Applications
edit2,5-Furandicarboxaldehyde can be used in the preparation of polyimine vitrimers.[2] It can also be applied as an alternative to glutaraldehyde as crosslinking agent for covalent enzyme immobilisation.[3]
See also
edit- Terephthalaldehyde (TA)
- 2,5-Furandicarboxylic acid (FDCA)
References
edit- ^ Zhou, Chunmei; Zhao, Jun; Sun, Haolin; Song, Yu; Wan, Xiaoyue; Lin, Hongfei; Yang, Yanhui (2019). "One-Step Approach to 2,5-Diformylfuran from Fructose over Molybdenum Oxides Supported on Carbon Spheres". ACS Sustainable Chemistry & Engineering. 7: 315–323. doi:10.1021/acssuschemeng.8b03470.
- ^ Dhers, S.; Vantomme, G.; Avérous, L. (2019). "A fully bio-based polyimine vitrimer derived from fructose" (PDF). Green Chemistry. 12 (7): 35676–35684. doi:10.1039/C9GC00540D. S2CID 104336119.
- ^ Danielli, C.; Van Langen, L.; Boes, D.; Asora, F.; Anselmi, S.; Provenza, F.; Renzi, M.; Gardossi, L. (2022). "2,5-Furandicarboxaldehyde as a bio-based crosslinking agent replacing glutaraldehyde for covalent enzyme immobilization". RSC Adv. 21 (7): 1596–1601. Bibcode:2022RSCAd..1235676D. doi:10.1039/D2RA07153C. PMC 9748790. PMID 36545099.