Abstract
A one pot-two step procedure for the synthesis of diethyl furan-2,5-dicarboxylate (DEFDC) starting from mucic acid without isolation of the intermediate furan dicarboxylic acid (FDCA) was studied. Then, the production of three different kinds of furan-based polyesters— polyethylene-2,5-furan dicarboxylate (PEF), polyhydropropyl-2,5-furan dicarboxylate(PHPF) and polydiglycerol-2,5-furandicarboxylate (PDGF)—was realized through a Co(Ac)2·4H2O catalyzed polytransesterification performed at 160 °C between DEFDC and a defined diol furan-based prepolymer or pure diglycerol. In parallel to polymerization process, an unattended regioselective 1-OH acylation of glycerol by direct microwave-heated FDCA diester transesterification led to the formation of a symmetric prepolymer ready for further polymerization and clearly identified by 2D NMR sequences. Furthermore, the synthesis of a more soluble and hydrophilic diglycerol-based furanic polyester was also achieved. The resulting biobased polymers were characterized by NMR, FT-IR spectroscopy, DSC, TGA and XRD. The morphologies of the resulted polymers were observed by FE-SEM and the purity of the material by EDX.
Highlights
Furandicarboxylic acid (FDCA) is recognized as one of the twelve building-block chemicals by the US Department of Energy
In order to achieve the polymerizations, this method required method required the preparation of prepolymers through solvent-free transesterifications between the preparation of prepolymers through solvent-free transesterifications thethe produced diethyl the produced diethyl furan-2,5-dicarboxylate (DEFDC)
FE- Scanning Electron Microscopy (SEM)- Energy Dispersive X-ray Diffraction (EDX) analysis of polymer powders was performed on a Quanta FEG 250 instrument (FEI, Hillsboro, OR, USA) equipped with a microanalysis detector for EDX from Bruker
Summary
FDCA is used to polymers replace thelike p-terephthalic acid (PTA), which is the field of commodity thermoplastic engineering the well-exploited polyethylene overall an oxidation product of p-xylene, aromatic compound issued from acid refined oil. This material obtained by reaction presence of EG [31] Another strategy to synthesize involves the ispolymerization of a prepolymer named bis(hydroxyethyl)-2,5-furandicarboxylate (BHEFDC) [32]. This material is obtained by reaction of DMFDC immersed in a large excess of EG and heated at temperatures between 160 and 220 °C. Were characterized and the morphology of the solid were observed by FE-SEM. by XRD, TGA and DSC analysis and the morphology of the solid were observed by FE-SEM
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