New families of 5-hydroxymethylfurfural derived biopolymers via acyclic diene metathesis polymerization

Diminishing oil reserves, increasing demand, and the rising costs of petroleum-based raw materials associated with waste production have has encouraged the industry to seek substitute feedstocks from renewable sources especially for plastics [1]. As a result, the interest in polymers synthesized from natural resources - such as polysaccharides, lignin and furan-based derivatives - has been growing worldwide. Among these compounds, 5-(hydroxymethyl)furfural (HMF)- synthesized easily from a carbohydrate source (mainly fructose) in high yield [2]- has quickly become the archetype of the bio-based platform chemicals having a wide range of applicability. HMF incorporates two functional units and an aromatic structure that renders this compound a versatile structure for the production of various derivatives. This derivatives in turn may be used as monomers for the synthesis of a selection of bio-based polymers. One well known example are polymers based on 2,5-furandicarboxylic acid (FDCA): poly(ethylene-2,5-furandicarboxylate) (PEF) and poly(butylene-2,5-furandicarboxylate) (PBF), which have the potential to replace their petroleum-derived counterparts: polyethylene terephthalate (PET) and polybutylene terephthalate (PBT) [3], due to their enhanced thermal an mechanical properties. Although over the past few years furan-based polymers have gathered special attention in the scientific community, their industry it’s still in its infancy. With that in mind, in this project we developed new furanic bio monomers, starting from HMF, that can be used has building block to synthetize via addition polymerization and acyclic diene metathesis (ADMET) polymerization, several families of furanic based biopolymers. The structure and the properties of the novel furanic-based polymers were then studied to evaluate their potential industrial applications.