Preparation of poly(ether ketone)s derived from 2,5-furandicarboxylic acid via nucleophilic aromatic substitution polymerization

From the viewpoint of the suppression of the petroleum consumption, aromatic poly(ether ketone)s (PEKs) were prepared by the nucleophilic aromatic substitution polymerization of 2,5-bis(4-fluorobenzoyl)furan (BFBF) synthesized from biomass and aromatic bisphenols. The model reaction of BFBF and p-methoxyphenol revealed that BFBF possessed enough reactivity for the nucleophilic aromatic substitution reactions. The polymerizations of BFBF and aromatic bisphenols afforded high molecular weight polymers with good yields in N-methylpyrrolidone and diphenyl sulfone for several hours. The longer polymerization time brought about the formation of insoluble parts in any solvents and reduction of molecular weight. The obtained PEKs were thermoplastics and exhibited good thermal stability, mechanical properties, and chemical resistance comparable to common high-performance polymers. The thermal properties were tunable with the structure of bisphenols.