Biocatalytic Synthesis of Furan-Based Oligomer Diols with Enhanced End-Group Fidelity

The lipase-catalyzed synthesis of furan-comprising polyester oligomer diols (alpha,omega-telechelic diols) is reported. Oligofuranoate diols with excellent end-group fidelity and a yield of 95% were synthesized using a solvent-free two-stage polycondensation of dimethyl furan-2,5-dicarboxylate (DMFDCA) and 1,4-cyclohexanedimethanol (1,4-CHDM) using immobilized Candida antarctica Lipase B (CalB). Recycling of immobilized CalB to further decrease the production cost is successfully demonstrated. However, it showed limitation in the product yield that decreases +/- 20% with each additional reuse. The synthetic procedure has been scaled up, easily opening the possibility to use the developed diols in industrial polycondensations utilizing the excellent flame retardancy property and high thermal stability typical for furan-based polymers.