2,5-Furandicarboxylic acid

Base Information

• Chemical Name: 2,5-Furandicarboxylic acid
• CAS No.: 3238-40-2
• Molecular Formula: C6H4O5
• Molecular Weight: 156.095
• Hs Code.: 29321900
• European Community (EC) Number: 221-800-8
• NSC Number: 40740
• UNII: 73C4JJ695C
• DSSTox Substance ID: DTXSID0062927
• Nikkaji Number: J7.694E
• Wikipedia: 2,5-Furandicarboxylic_acid
• Wikidata: Q4596798
• Metabolomics Workbench ID: 38548
• Mol file: 3238-40-2.mol

Synonyms:2,5-furandicarboxylic acid;FDCA cpd

Chemical Property of 2,5-Furandicarboxylic acid

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 8.9E-08mmHg at 25°C
• Melting Point: >310°C (dec.)
• Refractive Index: 1.58
• Boiling Point: 419.2 °C at 760 mmHg
• PKA: 2.28±0.10(Predicted)
• Flash Point: 207.3 °C
• PSA: 87.74000
• Density: 1.604 g/cm³
• LogP: 0.67600
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly Sonicated)
• Water Solubility.: 1g/L(18 oC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 156.00587322
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

99% or more ^*data from raw suppliers

2,5-Furandicarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36/37/39-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(OC(=C1)C(=O)O)C(=O)O
• Description: 2,5-Furandicarboxylic acid (FDCA) is an organic chemical compound consisting of two carboxylic acid groups attached to a central furan ring. It was first reported as dehydromucic acid by Rudolph Fittig and Heinzelmann in 1876, who produced it via the action of concentrated hydrobromic acid upon mucic acid. It can be produced from certain carbohydrates and as such is a renewable resource, it was identified by the US Department of Energy as one of 12 priority chemicals for establishing the “green” chemistry industry of the future.Furan-2,5-dicarboxylic acid (FDCA) has been suggested as an important renewable building block because it can substitute for terephthalic acid (PTA) in the production of polyesters and other current polymers containing an aromatic moiety.wikipedia
• Uses: Interest in renewable based polymers has led to 2,5-furandicarboxylic acid being proposed as a green, sustainable alternative to the widely used petroleum-based terephthalic acid in the synthesis of polyesters. 2,5-Furandicarboxylic acid is produced from oxidation of 5-hydroxymethylfurfural (HMF) which is obtained from the dehydration of bio-based sugars such as fructose. 2,5-Furandicarboxylic acid (FDCA) is a renewable, greener substitute for terephthalate in the production of polyesters. It is widely used as a precursor for the synthesis of bio-based polyesters and various other polymers.Applications of FDCA in the synthesis of several metal-organic frameworks (MOFs) have also been reported.

Technology Process of 2,5-Furandicarboxylic acid

There total 258 articles about 2,5-Furandicarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2,5-bis-(hydroxymethyl)furan (1883-75-6) → 5-Formyl-2-furancarboxylic acid (13529-17-4) + furan-2,5-dicarboxylic acid (3238-40-2)

Guidance literature:

With oxygen; sodium hydrogencarbonate; In water; at 90 ℃; for 10h; Reagent/catalyst; Catalytic behavior;

DOI:10.1016/j.jcat.2018.06.025

Reference yield: 92.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 5-Formyl-2-furancarboxylic acid (13529-17-4) + furan-2,5-dicarboxylic acid (3238-40-2)

Guidance literature:

With oxygen; In water; at 99.84 ℃; for 12h; under 3750.38 Torr; Reagent/catalyst;

DOI:10.1021/cs5003096

Reference yield: 82.0%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) → 2,5-diformylfurane (823-82-5,163857-09-8) + 5-Formyl-2-furancarboxylic acid (13529-17-4) + furan-2,5-dicarboxylic acid (3238-40-2)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from panus conchatus; oxygen; In aq. acetate buffer; at 25 ℃; for 96h; pH=4.5; Reagent/catalyst; Enzymatic reaction;

DOI:10.1039/c5gc00788g

upstream raw materials:

potassium furan-2-carboxylate

2,5-diformylfurane

D-glucose

Sucrose

Downstream raw materials:

2,5-furan-dicarboxylic acid monomethyl ester

furan-2,5-dicarboxylic acid dimethyl ester

furan-2,5-dicarbonitrile

terephthalic acid

Refernces

• 1、 Zhang, Pei,Zhang, Xiudong,Kang, Xinchen,Liu, Huizhen,Chen, Chunjun,Xie, Chao,Han, Buxing. "Salt-mediated synthesis of bimetallic networks with structural defects and their enhanced catalytic performances". . p. 12065 - 12068. Retrieved 2018.
• 2、 Miao, Zhenzhen,Wu, Tianxiao,Li, Jingwei,Yi, Ting,Zhang, Yibo,Yang, Xiangguang. "Aerobic oxidation of 5-hydroxymethylfurfural (HMF) effectively catalyzed by a Ce0.8Bi0.2O2-δ supported Pt catalyst at room temperature". . p. 19823 - 19829. Retrieved 2015.
• 3、 Teong, Siew Ping,Yi, Guangshun,Cao, Xueqin,Zhang, Yugen. "Poly-benzylic ammonium chloride resins as solid catalysts for fructose dehydration". . p. 2120 - 2124. Retrieved 2014.
• 4、 Zhao, Deyang,Delbecq, Frederic,Len, Christophe. "One-pot FDCA diester synthesis from mucic acid and their solvent-free regioselective polytransesterification for production of glycerol-based furanic polyesters". . . Retrieved 2019.
• 5、 Niu, Wenqi,Wang, Ding,Yang, Guohui,Sun, Jian,Wu, Mingbo,Yoneyama, Yoshiharu,Tsubaki, Noritatsu. "Pt nanoparticles loaded on reduced graphene oxide as an effective catalyst for the direct oxidation of 5-hydroxymethylfurfural (HMF) to produce 2,5-furandicarboxylic acid (FDCA) under mild conditions". . p. 1124 - 1129. Retrieved 2014.
• 6、 Zhang, Peili,Sheng, Xia,Chen, Xiaoyu,Fang, Zhiyong,Jiang, Jian,Wang, Mei,Li, Fusheng,Fan, Lizhou,Ren, Yansong,Zhang, Biaobiao,Timmer, Brian J. J.,Ahlquist, M?rten S. G.,Sun, Licheng. "Paired Electrocatalytic Oxygenation and Hydrogenation of Organic Substrates with Water as the Oxygen and Hydrogen Source". . p. 9155 - 9159. Retrieved 2019.
• 7、 Masoud, Nazila,Donoeva, Baira,de Jongh, Petra E.. "Stability of gold nanocatalysts supported on mesoporous silica for the oxidation of 5-hydroxymethyl furfural to furan-2,5-dicarboxylic acid". . p. 150 - 157. Retrieved 2018.
• 8、 Shen, Guanfei,Zhang, Sicheng,Lei, Yu,Chen, Zhuqi,Yin, Guochuan. "Synthesis of 2,5-furandicarboxylic acid by catalytic carbonylation of renewable furfural derived 5-bromofuroic acid". . p. 204 - 209. Retrieved 2018.
• 9、 Musella, Elisa,Gualandi, Isacco,Scavetta, Erika,Rivalta, Arianna,Venuti, Elisabetta,Christian, Meganne,Morandi, Vittorio,Mullaliu, Angelo,Giorgetti, Marco,Tonelli, Domenica. "Newly developed electrochemical synthesis of Co-based layered double hydroxides: Toward noble metal-free electro-catalysis". . p. 11241 - 11249. Retrieved 2019.
• 10、 Cai, Jiaying,Ma, Hong,Zhang, Junjie,Song, Qi,Du, Zhongtian,Huang, Yizheng,Xu, Jie. "Gold nanoclusters confined in a supercage of Y zeolite for aerobic oxidation of HMF under mild conditions". . p. 14215 - 14223. Retrieved 2013.