2,5‐Furandicarboxylic Acid Synthesis and Use

Huang, Ying-Ting; Wong, Jinn-Jong; Huang, Cheng-Jyun; Li, Chia‐Ling; Jang, Guang-Way Bill

doi:10.1002/9783527698202.ch8

Cited by 12 publications

(5 citation statements)

References 49 publications

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“…FDCA is a biobased monomer synthesized by oxidation of 5-hydroxymethylfurfural, which is by turn the dehydration product of hexoses such as fructose and glucose. − There are many new research works that implement FDCA as an alternative (co)monomer to petroleum-based terephthalic acid (TPA), which is vastly used in the synthesis of aromatic polyesters, notably polyethylene terephthalate (PET) and polybutylene terephthalate (PBT). This trend favoring FDCA stems from the structural similarities between both monomers as both are aromatic rings with two oppositely positioned carboxylic groups. , In addition, the FDCA bioproduction route is easily accessible when compared to the challenging and inefficient TPA bioproduction. − The structures of both TPA and FDCA are given in Scheme . When polymerized, aromatic polyesters produced from FDCA instead of TPA show very competitive properties that are in some cases considered to be far superior to TPA-based polyesters. − …”

Section: Introductionmentioning

confidence: 99%

“…This trend favoring FDCA stems from the structural similarities between both monomers as both are aromatic rings with two oppositely positioned carboxylic groups. 9,10 In addition, the FDCA bioproduction route is easily accessible when compared to the challenging and inefficient TPA bioproduction. 11−14 The structures of both TPA and FDCA are given in Scheme 1.…”

Section: ■ Introductionmentioning

confidence: 99%

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The Impact of Diethyl Furan-2,5-dicarboxylate as an Aromatic Biobased Monomer toward Lipase-Catalyzed Synthesis of Semiaromatic Copolyesters

Nasr

Favrelle-Huret²,

Mincheva

et al. 2022

ACS Appl. Polym. Mater.

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Furan-2,5-dicarboxylic acid has been introduced in recent years as a green aromatic monomer toward the design of aromatic (co)polyesters with enhanced properties, i.e., polyethylene furanoate (PEF) that can definitely compete with its petroleum-based counterpart, i.e., polyethylene terephthalate (PET). In an attempt to produce biobased semiaromatic copolyesters in an efficient eco-friendly approach, we report herein the polycondensation of diethyl furan-2,5-dicarboxylate (DEFDC) with different aliphatic diols and diesters of variable chain length catalyzed by an immobilized lipase from Candida antarctica using a two-step polymerization reaction carried out in diphenyl ether. The influence of diol and diester chain length, the molar concentration of DEFDC, and the effect of enzyme loading were assessed via nuclear magnetic resonance (NMR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and wide-angle X-ray scattering (WAXS). With high quantities of DEFDC, significant differences in terms of M̅ n buildup were noticed. Only longer diols starting from octane-1,8-diol successfully reacted with up to 90% DEFDC as opposed to only 25% DEFDC reacting with short diols such as butane-1,4-diol. While varying the chain length of the diester, it was evident that shorter diols such as hexane-1,6-diol have better reactivity toward longer diesters, while dodecane-1,12-diol was reactive toward all tested diesters. The incorporation of long chain fatty dimer diols such as Pripol 2033 led to polyesters with higher M̅ n and was successfully used to overcome the limitations of poor reactivity observed in the case of short diols in the presence of high furan content. The DSC results showed a pseudoeutectic behavior as a function of increasing the mol % of DEFDC, and a change in the crystalline phase was confirmed via WAXS analysis. Finally, this work showed the successful enzyme-catalyzed synthesis of several DEFDC biobased semiaromatic copolyesters with variable interesting properties that can be further optimized for possible applications in food packaging as well as other possibilities.

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

The Impact of Diethyl Furan-2,5-dicarboxylate as an Aromatic Biobased Monomer toward Lipase-Catalyzed Synthesis of Semiaromatic Copolyesters

Nasr

Favrelle-Huret²,

Mincheva

et al. 2022

ACS Appl. Polym. Mater.

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“…4 To date, enough evidence has clearly supported the fact that FDCA can be employed as a furan-based surrogate of terephthalic acid in polymer syntheses. 5,6 Commercial FDCA is often produced through catalytic oxidation of hydroxymethylfurfural (HMF), 7–9 which can be ideally produced from bulky celluloses through hydrolysis and dehydration. However, because of great challenges during cellulose hydrolysis, HMF is currently obtained from glucose and/or fructose, 10,11 which is competitive with the food supply of human beings.…”

Section: Introductionmentioning

confidence: 99%

Photo-responsive liquid crystalline polymer from a renewable furfural derivative of dimethyl 2,5-furandicarboxylate via catalytic carbonylative esterification

et al. 2022

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“…The oxidation of HMF to FDCA is a complex cascade process involving several intermediates in parallel or successive reactions (Figure 1) [8]. The first step of the process can imply either the oxydehydrogenation of the alcohol group of HMF to aldehyde, forming 2,5-diformylfuran (DFF), or the oxidation of the carbonyl group to carboxylic acid into 5-hydroxymethyl-2-furancarboxylic acid (HMFCA).…”

Section: Introductionmentioning

confidence: 99%

5-Hydroxymethylfurfural Oxidation to 2,5-Furandicarboxylic Acid on Noble Metal-Free Nanocrystalline Mixed Oxide Catalysts

et al. 2022

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Noble metal-free catalysts based on earth-abundant and inexpensive mixed oxides are active catalysts of all steps of the reaction cascade leading from 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) using tert-butyl hydroperoxide (TBHP) as oxidation agent. Catalysts covering the whole range of composition in the Cu-Mn and Co-Fe series have been prepared and characterised. The nature and composition of the catalyst strongly affect conversion and selectivity. The distribution of products indicates that radical-type oxygen species, deriving from the activation of TBHP, play a determining role in the reaction. The early steps of reaction mainly follow the pattern expected for heterogeneous Fenton catalysts. Mixed oxide catalysts are the most effective in further oxidation steps, leading to the formation of FDCA, both in the Cu-Mn and Co-Fe systems. This behaviour can be related to the distribution of charge in the mixed oxides, suggesting a possible implication of the lattice oxygen in the last reaction steps. The results provide indications on how to optimize the reaction and minimize the formation of byproducts (humins and oligomers).

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2,5‐Furandicarboxylic Acid Synthesis and Use

Cited by 12 publications

References 49 publications

The Impact of Diethyl Furan-2,5-dicarboxylate as an Aromatic Biobased Monomer toward Lipase-Catalyzed Synthesis of Semiaromatic Copolyesters

The Impact of Diethyl Furan-2,5-dicarboxylate as an Aromatic Biobased Monomer toward Lipase-Catalyzed Synthesis of Semiaromatic Copolyesters

Photo-responsive liquid crystalline polymer from a renewable furfural derivative of dimethyl 2,5-furandicarboxylate via catalytic carbonylative esterification

5-Hydroxymethylfurfural Oxidation to 2,5-Furandicarboxylic Acid on Noble Metal-Free Nanocrystalline Mixed Oxide Catalysts

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