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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.
2,5-Furandicarboxylic acid fast facts
|CAS Reg. No.||3238-40-2|
|Molar mass||156.09 g/mol|
|Melting point||342 ºC|
|Water solubility||≈1 g/L|
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