A novel 2,5-furandicarboxylic acid-based bis(cyclic carbonate) for the synthesis of biobased non-isocyanate polyurethanes

Abstract

This paper describes the synthesis of a new biobased bis(cyclic carbonate) derived from 2,5-furandicarboxylic acid (FDCA) with the incorporation of CO 2 . The bis(cyclic carbonate) was then used to synthesize non-isocyanate polyurethanes (NIPUs) via polyaddition reactions with a series of diamines. The chemical structures of the bis(cyclic carbonate) and the NIPUs were characterized by Fourier transform infrared spectroscopy (FT-IR) and proton nuclear magnetic resonance spectroscopy

From the Synthesis of Biobased Cyclic Carbonate to Polyhydroxyurethanes: A Promising Route towards Renewable Non‐Isocyanate Polyurethanes

“…Zhang et al described an ovel method to obtain 2,5furan-bis-CC through at hree-stepp rocedure (Figure 4). [117] FDCA is reactedw ith allyl bromide through the dehydrobromination reaction, followed by epoxidationw ith m-CPBA. Finally, the diglycidyl ester of FDCA is carbonated with CO 2 ,l eadingt o 2,5-furan-bis-CC.…”

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

“…[119] TA derivative 4b was earlier synthesized by Endo and co-workersb yc oupling GD and terephthaloyl chloride (TC) followed by carbonation at 100 8Ci n NMP with LiBr as catalyst. To develop more sustainable alternatives to carbonates 4a-d as rigid aromatic buildingb locks for the synthesis of PHUs, Li and coworkers [123] prepared 4e from 2,5-furandicarboxylic acid (FDCA). [121] Additional aromatic rigid building blocks 4c and 4d were used by Torkelson and co-workers for preparing carbonate-based hard segmentsi nP HU thermoplastics.…”

“…[118,122] These monomersw ere synthesized from the corresponding glycidyl bisepoxide by using TBAI as catalyst at 80 8C. To develop more sustainable alternatives to carbonates 4a-d as rigid aromatic buildingb locks for the synthesis of PHUs, Li and coworkers [123] prepared 4e from 2,5-furandicarboxylic acid (FDCA). FDCA can be produced by catalytic [124] or enzymatic strategies [125] from the oxidationo fn on-food-sourced, renewable, hydroxymethyl furfural (HMF) [126] and is regarded as a potentially renewablea lternative to TA.…”

Synthesis of Glux based polymers for removal of benzene derivatives and pesticides from water

“…The furanic compounds, specifically the 2,5-furandicarboxilic acid, are potentially useful for the synthesis of nonpetroleum-derived polymeric materials such as polyesters, polyamides, and polyurethanes. 21,22 In recent times, another family of based-carbohydrate bicyclic monomers with a diacetal constitution has emerged. These bicyclic diacetalized sugar derivatives, mainly diols and diacids, have shown a good potential for polymers synthesis at least comparable to that of isohexides.…”