Enzymatic Synthesis of Copolyesters with the Heteroaromatic Diol 3,4-Bis(hydroxymethyl)furan and Isomeric Dimethyl Furandicarboxylate Substitutions.

Autor: Silvianti F; Macromolecular Chemistry & New Polymeric Materials, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen 9747 AG, The Netherlands., Maniar D; Macromolecular Chemistry & New Polymeric Materials, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen 9747 AG, The Netherlands., Agostinho B; CICECO─Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Aveiro 3810-193, Portugal., de Leeuw TC; CarbExplore Research B.V., Groningen 9747 AA, The Netherlands., Woortman AJJ; Macromolecular Chemistry & New Polymeric Materials, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen 9747 AG, The Netherlands., van Dijken J; Macromolecular Chemistry & New Polymeric Materials, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen 9747 AG, The Netherlands., Thiyagarajan S; Wageningen Food & Biobased Research, Wageningen University and Research, P.O. Box 17, Wageningen 6700 AA, The Netherlands., Sousa AF; CICECO─Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, Aveiro 3810-193, Portugal.; Centre for Mechanical Engineering, Materials and Processes, Department of Chemical Engineering, University of Coimbra Rua Sílvio Lima─Polo II, Coimbra 3030-790, Portugal., Loos K; Macromolecular Chemistry & New Polymeric Materials, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, Groningen 9747 AG, The Netherlands.
Jazyk: angličtina
Zdroj: Biomacromolecules [Biomacromolecules] 2024 May 13; Vol. 25 (5), pp. 2792-2802. Date of Electronic Publication: 2024 Apr 11.
DOI: 10.1021/acs.biomac.3c01433
Abstrakt: Polyesters from furandicarboxylic acid derivatives, i.e., dimethyl 2,5-furandicarboxylate (2,5-DMFDCA) and 2,4-DMFDCA, show interesting properties among bio-based polymers. Another potential heteroaromatic monomer, 3,4-bis(hydroxymethyl)furan (3,4-BHMF), is often overlooked but holds promise for biopolymer synthesis. Cleaning and greening synthetic procedures, i.e., enzymatic polymerization, offer sustainable pathways. This study explores the Candida antarctica lipase B (CALB)-catalyzed copolymerization of 3,4-BHMF with furan dicarboxylate isomers and aliphatic diols. The furanic copolyesters (co-FPEs) with higher polymerization degrees are obtained using 2,4-isomer, indicating CALB's preference. Material analysis revealed semicrystalline properties in all synthesized 2,5-FDCA-based co-FPEs, with multiple melting temperatures ( T m ) from 53 to 124 °C and a glass-transition temperature ( T g ) of 9-10 °C. 2,4-FDCA-based co-FPEs showed multiple T m from 43 to 61 °C and T g of -14 to 12 °C; one of them was amorphous. In addition, all co-FPEs showed a two-step decomposition profile, indicating aliphatic and semiaromatic segments in the polymer chains.
Databáze: MEDLINE