Production of 100% bio-based semi-aromatic nylon by aerobic oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid with bio aliphatic diamine

The development of sustainable polymers from biomass-based feedstocks has become a hot topic in both academia and industry. In this study, aerobic oxidation of 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid (FDCA) catalyzed by fluorous silica gel-supported perfluoro-tagged gold nanoparticles was first reported. With the aid of this highly active catalyst, a maximum HMF conversion of 100% with 91% FDCA selectivity was achieved, and the catalyst could be used 3 times without significant loss of activity. The nylon salts 5F (1,5-pentylenediamine-FDCA) and 10F (1,10-decylenediamine-FDCA) were then prepared through crystallization, and their single crystal structures were first determined by single X-ray diffraction. Finally, 100% bio-based semi-aromatic nylon 5F and 10F were obtained by the melt polymerization of the nylon 5F and 10F salt, and their structural and thermodynamic properties have been systematically investigated. The results showed these transparent bio-based nylon materials have potential application as functional additives, temperature responsive materials or general plastics in conduits and household plastic devices.