A two-step efficient preparation of a renewable dicarboxylic acid monomer 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid] from d-fructose and its application in polyester synthesis

Abstract

A renewable monomer 5,5′-[oxybis(methylene)]bis[2-furancarboxylic acid] from d-fructose.

Solvent‐Free Catalytic Self‐Etherification of 5‐Hydroxymethyl Furfural

“…In agreement with the previous reports CH 2 Cl 2 was the best reaction media. Recently Amarasekara et al., reported a notable example of a one‐pot synthesis of OBMF from fructose in 76 % yield using Dowex 50 W X8 acid resin as catalyst and DMSO as a solvent. In 2016, Galkin et al .…”

Preyssler Heteropolyacids in the Self‐Etherification of 5‐Hydroxymethylfurfural to 5,5′‐[Oxybis(methylene)]bis‐2‐furfural Under Mild Reaction Conditions

“…Recently, similar yields to OBMF (96 %) were obtained by Shinde and Rode who used a Sn catalyst supported on montmorillonite, but this yield was only reached with the elimination of water, which favors OBMF formation . Recently, Amarasekara et al., obtained OBMF from fructose with 76 % yield using acid resin as the catalyst and DMSO as the solvent at 383 K . Additionally, the OBMF was oxidized to 5,5′‐[oxybis(methylene)]bis[2‐furancarboxylic acid] (OBFC) to obtain the dimer of 2,5‐furan dicarboxylic acid (FDCA) as the principal product.…”

Oxidative NHC‐Catalysis as Organocatalytic Platform for the Synthesis of Polyester Oligomers by Step‐Growth Polymerization

“…In recent years, DFF and difuranic OBFAh ave been employed as monomers to prepare furan-urea resins and imine-based polymers, [25,26] but also as suitable precursors of the corresponding diacids, that are 2,5-furandicarboxylica cid (FDCA) [27] and 5,5'-oxybis(methylene)bis2-furancarboxylic acid (OBFC). [28] To day,F DCA is widely recognized as an effective equivalent of terephthalic acid fort he synthesis of PEs from renewable resources;i np articular,p oly(ethylene furanoate) (PEF) has emerged as an innovative alternative to PET with attractive mechanical and barrier properties, [29] and some companies are presentlyb uilding plants for its productiono nal arge scale. Similarly,t he difuranic-diacid OBFC is under investigation for the synthesis of novel polyester-ether materials, including the promising poly(ethylene 5,5'-(oxybis(methylene)bis(2-furancarboxylate))) (PEOBF).…”

“…Similarly,t he difuranic-diacid OBFC is under investigation for the synthesis of novel polyester-ether materials, including the promising poly(ethylene 5,5'-(oxybis(methylene)bis(2-furancarboxylate))) (PEOBF). [28] Hence, PEF and PEOBFo ligomers 3ac (M n = 1.5 kg mol À1 )a nd 3ad (M n = 3.5 kg mol À1 )w ere readily prepared by using our complementary oxidative strategy,d i-rectly starting from DFF and OBFAd ialdehydes 2c,d in place of the corresponding acids FDCA and OBFC (entries 6a nd 7).…”