Molecule of the Week

2,5-Furandicarboxylic acid

November 13, 2017

Fully sustainable plastic bottles may be in my future. What molecule am I?

In 1876, German chemist Wilhelm Rudolf Fittig synthesized 2,5-furandicarboxylic acid (then called dehydromucic acid) from acyclic, sugar-derived galactaric (mucic) acid. 2,5-Furandicarboxylic acid, or FDCA, did not draw much interest until the past several years, when it was recognized as a potential sustainable monomer for polyester manufacturing.

Chemical/biochemical companies DuPont, Corbion, and Synvina (a BASF–Avantium joint venture) have developed efficient syntheses of FDCA from 5-(hydroxymethyl)furfural and 5-(methoxymethyl)furfural, both of which can be made from natural fructose. Along with biobased ethylene glycol, this biobased FDCA can be used to make sustainable poly(ethylene furanoate) (PEF), a polyester that has properties similar to those of the widely used poly(ethylene terephthalate) (PET).

PEF actually provides better gas barrier than PET, making it an excellent candidate for making plastic bottles for carbonated beverages. But PEF’s differences from PET mean that soda bottles and other plastic packaging materials would have to be redesigned. That, in addition to scaling up the manufacture of FDCA, dictates that large-scale replacement of PET with PEF is a long way off.

As a start, Synvina is building a 50,000 t/year FDCA plant in Antwerp, Belgium; and DuPont is nearing the completion of a 60 t/year pilot plant at Decatur, IL, to make 2,5-furandicarboxylic monomethyl ester, an FDCA derivative that can also be used to make PEF.

Learn more about this week’s molecule from the CAS REGISTRY, which is searched using SciFinder®. Each record displays the registry number, index name and synonyms, bibliographic information, and more.

Molecule of the Week: 3d: 2,5-Furandicarboxylic acid
Molecule of the Week: 2d: 2,5-Furandicarboxylic acid

2,5-Furandicarboxylic acid fast facts

CAS Reg. No. 3238-40-2
Molar mass 156.09 g/mol 
Formula C6H4O5
Appearance White solid 
Melting point 342 ºC
Water solubility ≈1 g/L

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