Modern petroleum-derived polymers have found extensive use as thermoplastic engineering materials, but their synthesis and disposal remains environmentally challenging. Moreover, the shale gas boom has put pressure on the markets for appropriate monomer feedstocks. Consequently, biobased polymers have been targeted as replacements by utilizing biomass-derived, renewable feedstocks. An added benefit to this approach is that the final products are often degradable, leading to decreases in landfilled waste. However, only poly(lactic acid) (PLA) has yet found broad commercial success as a thermoplastic. PLA has mostly been used in the disposable packaging market because it is similar in certain respects to polystyrene and polyethylene terephthalate. It has not found broader acceptance because its chemical structure yields a low glass transition temperature (Tg) of only 60 °C, and it is susceptible to hydrolytic degradation. In this work, we demonstrate the production of an alternative polymer with tunable functionality, opening the door to a class of materials that share polymerization chemistry but lead to a range of physical properties. 5-hydroxymethylfurfural (HMF), obtained from cellulose dehydration, is used as a platform chemical which can be coupled with phenols obtained via lignin pyrolysis. The HMF undergoes etherification with the phenols, and the phenolic side chain is retained in the final polymer. The HMF-ether is then rearranged to yield a delta-hexalactone functionalized with the same pendant group as was present on the HMF ether. This functionalized lactone is subjected to ring-opening transesterification polymerization, leading to materials with Tg that depend on the identity of the side chain and should be degradable according to the same enzymatic mechanisms that lead to PLA degradation.

Renewable, tunable polymers from lignin and 5-hydroxymethylfurfural

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.