High-Performance Thermoplastics from a Unique Bicyclic Lignin-Derived Diol

Autor: Xianyuan Wu, Mario De bruyn, Gregor Trimmel, Klaus Zangger, Katalin Barta
Přispěvatelé: Synthetic Organic Chemistry
Rok vydání: 2023
Předmět:
Zdroj: ACS Sustainable Chemistry and Engineering, 11(7), 2819-2829. AMER CHEMICAL SOC
ISSN: 2168-0485
DOI: 10.1021/acssuschemeng.2c05998
Popis: Polyesters are an important class of thermoplastic polymers, and there is a clear demand to find high-performing, recyclable, and renewable alternatives. In this contribution, we describe a range of fully bio-based polyesters obtained upon the polycondensation of the lignin-derived bicyclic diol 4,4′-methylenebiscyclohexanol (MBC) with various cellulose-derived diesters. Interestingly, the use of MBC in combination with either dimethyl terephthalate (DMTA) or dimethyl furan-2,5-dicarboxylate (DMFD) resulted in polymers with industrially relevant glass transition temperatures in the 103-142 °C range and high decomposition temperatures (261-365 °C range). Since MBC is obtained as a mixture of three distinct isomers, in-depth NMR-based structural characterization of the MBC isomers and thereof derived polymers is provided. Moreover, a practical method for the separation of all MBC isomers is presented. Interestingly, clear effects on the glass transition, melting, and decomposition temperatures, as well as polymer solubility, were evidenced with the use of isomerically pure MBC. Importantly, the polyesters can be efficiently depolymerized by methanolysis with an MBC diol recovery yield of up to 90%. The catalytic hydrodeoxygenation of the recovered MBC into two high-performance specific jet fuel additives was demonstrated as an attractive end-of-life option.
Databáze: OpenAIRE