Abstract
A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (Tg) than those prepared from their primary diol equivalents. Two methods of polymerisation were investigated, the first employing activation of the aromatic diacids via the corresponding diacid chlorides and the second using a transesterification procedure. Longer chain diols were found to be more reactive than the shorter chain alternatives, generally giving rise to higher molecular weight polymers, an effect shown to be most pronounced when using the transesterification route. Finally, novel diesters with high degrees of branching in their hydrocarbon chains are introduced as potential monomers for possible low surface energy materials applications.
Highlights
Current industrial processing methods enable mega-scale production of diverse classes of polymeric materials with a wide range of properties
We report in detail on the synthesis of novel polyesters from monomers having a common precursor in the form of biomass-derived 5(chloromethyl)furfural (CMF) 1
When the duration was reduced in one case to 24 hours for the reaction between 3 and 7, the isolated yield of polymer decreased from 61% to 27%, with a concomitant reduction in the polymer chain length
Summary
Current industrial processing methods enable mega-scale production of diverse classes of polymeric materials with a wide range of properties. The production of industrial polymers maintains a disquieting reliance on non-renewable fossil resources, raising concerns regarding the longterm sustainability of this key sector of the chemical industry. Markets in this area have tended to be somewhat conservative, focusing their development around the use of conventional and readily available monomers, such as light ole ns, acrylates, styrene, butadiene, ethylene glycol and terephthalic acid, which together account for the great majority of the plastics market. We further introduce two new bio-based diesters that showcase the versatility of the CMF derivative levulinic acid 5 as a source of novel monomers.
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