One-step synthesis of furan-2,5-dicarboxylic acid from furan-2-carboxylic acid using carbon dioxide

Fischer, Róbert; Fišerová, M.

doi:10.3998/ark.5550190.p008.285

Cited by 9 publications

(5 citation statements)

References 17 publications

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“…Also in 2013, Fischer reported another method for FDCA synthesis from furoic acid through its C–H carboxylation with CO 2 under strong alkaline conditions . With the use of n -BuLi or lithium diisopropylamide as the base, FDCA could be obtained in 73% yield in THF at 195 K. Alternatively, Kanan explored another carboxylation method for FDCA synthesis from furoate at an elevated temperature (Scheme ).…”

Section: Bifunctionalized Furan Monomersmentioning

confidence: 99%

“…Also in 2013, Fischer reported another method for FDCA synthesis from furoic acid through its C−H carboxylation with CO 2 under strong alkaline conditions. 187 With the use of n-BuLi or lithium diisopropylamide as the base, FDCA could be obtained in 73% yield in THF at 195 K. Alternatively, Kanan explored another carboxylation method for FDCA synthesis from furoate at an elevated temperature (Scheme 18). 188,189 The carboxylation reaction was conducted by heating the mixtures of cesium furoate and Cs 2 CO 3 at 473 K under 8 bar of CO 2 , which provided an 89% yield of FDCA salt in 5 h. The reaction was proposed to take place at the molten salt−CO 2 interface, and the merit of cesium salt was attributed to its lower melting points compared with those of other metal salts, thus making the meltion happen at a relatively low temperature.…”

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confidence: 99%

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Catalytic Transformation of the Furfural Platform into Bifunctionalized Monomers for Polymer Synthesis

Zhu

Yin

2021

ACS Catal.

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Furfural is currently industrially produced from raw agricultural materials with almost no limit; however, its market volume is very limited due to its monofunctionalized furan structure. Apparently, the exploration of new catalytic technologies to transform furfural into versatile bifunctionalized monomers for polymer syntheses may substantially open up furfural-based biomass utilizations and partially reduce concerns about the scarcity of the carbon source in the chemical industry caused by the rapid depletion of fossil resources. This Review summarizes the current state of the art of bifunctional monomer development from the furfural platform, including aliphatic diols, diacids and anhydrides, bifunctionalized furans and bifurans, and furan-based bisphenol A analogues. We hope the coming success in catalytic efficiency improvements in these monomer syntheses from the furfural platform with related polymer developments may boost furfural-based hemicellulose utilizations.

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Section: Bifunctionalized Furan Monomersmentioning

confidence: 99%

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confidence: 99%

Catalytic Transformation of the Furfural Platform into Bifunctionalized Monomers for Polymer Synthesis

Zhu

Yin

2021

ACS Catal.

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“…In exploring an alternative route for FDCA synthesis, Pan et al even reported the synthesis of FDCA through disproportionation of furoic acid with the formation of furan, while Pan, Fischer, Dick and Banerjee et al independently explored the C–H carboxylations of furoic acid with CO 2 to FDCA under strong alkaline conditions or with carbonate promoter. − We recently developed a four-step synthesis of FDCA from furoic acid through bromination, esterification, carbonylation, and hydrolysis and a one-step synthesis of another HMF derivative through oxidative carbonylation of furfuryl acetate. , Although these new processes are still lengthy or low efficiency, the new developments have convinced us that transforming furfural-based platforms to HMF derivatives is accessible. Here, we present an efficient one-step synthesis of FDCA from 5-bromo-furoic acid through aqueous-phase carbonylation.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of 2,5-Furandicarboxylic Acid from Furfural Based Platform through Aqueous-Phase Carbonylation

Zhang

Shen

Deng

et al. 2018

ACS Sustainable Chem. Eng.

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Deriving bulk chemicals from sustainable biomass for chemical industries has become a worldwide consensus because of the rapid depletion of fossil feedstock. Here, synthesis of 2,5-furandicarboxylic acid (FDCA), an alternative to p-phthalic acid, from furfural based platform molecule was explored. Using 5-bromo-furoic acid as the starting chemical which has been industrially available through bromination of furoic acid, 98% yield of FDCA can be achieved by catalytic carbonylation in aqueous solution with palladium catalyst, and FDCA separation can be easily performed through simple acidification of reaction media in large-scale synthesis. This new route to FDCA has offered furfural a promising subchemical with a large market. Meanwhile, it also provides an alternative source to FDCA originating from C5 based bulk biomass, that is, hemicellulose, thus offering an opportunity to relieve the current stress in FDCA synthesis from 5-hydroxymethylfurfural originally from cellulose to replace p-phthalic acid in polymer industry.

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“…This regioselectivity was proposed to be strongly dependent on the type of lithium species used . In contrast, Fischer and Fišerová observed the inversion of regioselectivity in favor of the 2,3‐regioisomer (Scheme ). They studied the one‐step carboxylation of furoic acid by using CO 2 and n ‐butyllithium or LDA (lithium diisopropylamide).…”

Section: Homogeneous Catalysismentioning

confidence: 99%

Recent Advances in Carboxylation of Furoic Acid into 2,5‐Furandicarboxylic Acid: Pathways towards Bio‐Based Polymers

et al. 2020

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2,5-furandicarboxylic acid (FDCA) is one of the most important bio-sourced building blocks and several routes have been reported for its synthesis. FDCA is presumed to be an ideal green alternative to terephthalate, which is one of the predominant monomers in polymer industry. This Minireview concerns the synthesis of FDCA by using various carboxylation reactions and discusses the synthesis of FDCA starting from furoic acid and CO 2 and using different catalytic and stoichiometric processes. This process is of high interest, as it avoids the glucose isomerization step and selectivity issues observed during the 5-hydroxymethylfurfural oxidation step of the current alternative route to FDCA. Discussion focuses on the main parameters that govern selectivity and activity in the carboxylation processes. Moreover, various previously described processes, such as the Henkel reaction and enzymatic, homogeneous catalytic, and photoelectrocatalytic processes, are also discussed.

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One-step synthesis of furan-2,5-dicarboxylic acid from furan-2-carboxylic acid using carbon dioxide

Cited by 9 publications

References 17 publications

Catalytic Transformation of the Furfural Platform into Bifunctionalized Monomers for Polymer Synthesis

Catalytic Transformation of the Furfural Platform into Bifunctionalized Monomers for Polymer Synthesis

Efficient Synthesis of 2,5-Furandicarboxylic Acid from Furfural Based Platform through Aqueous-Phase Carbonylation

Recent Advances in Carboxylation of Furoic Acid into 2,5‐Furandicarboxylic Acid: Pathways towards Bio‐Based Polymers

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