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Molecules 2019, 24(6), 1030; https://doi.org/10.3390/molecules24061030

One-Pot FDCA Diester Synthesis from Mucic Acid and Their Solvent-Free Regioselective Polytransesterification for Production of Glycerol-Based Furanic Polyesters

1
Sorbonne Universités, Université de Technologie de Compiègne, Centre de Recherches de Royallieu, CS 60319, F-60203 Compiègne CEDEX, France
2
PSL Research University, Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences, 11 rue Pierre et Marie Curie, F-75231 Paris CEDEX 05, France
3
Ecole Supérieure de Chimie Organique et Minérale, 1 allée du Réseau Jean-Marie Buckmaster, F-60200 Compiègne, France
*
Author to whom correspondence should be addressed.
Received: 17 February 2019 / Revised: 7 March 2019 / Accepted: 8 March 2019 / Published: 15 March 2019
(This article belongs to the Special Issue Biorefinery and Biomass Conversion and Utilization)
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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. View Full-Text
Keywords: mucic acid dehydration; FDCA diesters; regioselective transesterification; poly-transesterification mucic acid dehydration; FDCA diesters; regioselective transesterification; poly-transesterification
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Zhao, D.; Delbecq, F.; Len, C. One-Pot FDCA Diester Synthesis from Mucic Acid and Their Solvent-Free Regioselective Polytransesterification for Production of Glycerol-Based Furanic Polyesters. Molecules 2019, 24, 1030.

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