2,5-Furandicarboxaldehyde
Names
Other names
Furan-2,5-dicarboxaldehyde, 2,5-Diformylfuran
Identifiers
3D model (JSmol)
Abbreviations FDC
ChEBI
ChemSpider
ECHA InfoCard 100.011.382
EC Number
  • 212-520-7
KEGG
UNII
  • InChI=1S/C6H4O3/c7-3-5-1-2-6(4-8)9-5/h1-4H
    Key: KUCOHFSKRZZVRO-UHFFFAOYSA-N
  • C1=C(OC(=C1)C=O)C=O
Properties
C6H4O3
Molar mass 124.095 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
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).
Infobox references

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.[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.

Applications

2,5-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

References

  1. ↑ Zhou, C.; Zhao, J.; Sun, H.; Song, Y.; Wan, X.; Lin, H.; Yang, Y. (2019). "One-Step Approach to 2,5-Diformylfuran from Fructose over Molybdenum Oxides Supported on Carbon Spheres". ACS Sustainable Chem. Eng. 7 (1): 315–323. doi:10.1039/c6py01395c.
  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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