2,5-Furandicarboxylic acid

2,5-Furandicarboxylic acid
Names
Preferred IUPAC name
Furan-2,5-dicarboxylic acid
Other names
Dehydromucic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.019.819
UNII
  • InChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10) Y
    Key: CHTHALBTIRVDBM-UHFFFAOYSA-N Y
  • InChI=1/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)
    Key: CHTHALBTIRVDBM-UHFFFAOYAD
  • C1=C(OC(=C1)C(=O)O)C(=O)O
  • O=C(O)c1oc(C(=O)O)cc1
Properties
C6H4O5
Molar mass 156.093 g·mol−1
Appearance White solid
Density 1.604 g/cm3
Melting point 342 °C (648 °F; 615 K)
Boiling point 420 °C (788 °F; 693 K)
soluble in DMSO
Acidity (pKa) 4.38, 5.85
Hazards
Flash point 207 °C (405 °F; 480 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future. Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.