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2,5-Furandicarboxaldehyde

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2,5-Furandicarboxaldehyde
Names
Other names Furan-2,5-dicarboxaldehyde, 2,5-Diformylfuran
Identifiers
CAS Number
3D model (JSmol)
Abbreviations FDC
ChEBI
ChemSpider
ECHA InfoCard 100.011.382 Edit this at Wikidata
EC Number
  • 212-520-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4O3/c7-3-5-1-2-6(4-8)9-5/h1-4HKey: KUCOHFSKRZZVRO-UHFFFAOYSA-N
SMILES
  • C1=C(OC(=C1)C=O)C=O
Properties
Chemical formula C6H4O3
Molar mass 124.095 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements 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 , 100 kPa). Infobox references
Chemical compound

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.

Synthesis

2,5-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. 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.

Applications

2,5-Furandicarboxaldehyde can be used in the preparation of polyimine vitrimers. It can also be applied as an alternative to glutaraldehyde as crosslinking agent for covalent enzyme immobilisation.

See also

References

  1. 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.
  2. 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.
  3. 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.
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