2,5-Furandicarboxylic acid CAS#: 3238-40-2; ChemWhat Code: 25627

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Other DataApproved Manufacturers

Identification

Product Name2,5-Furandicarboxylic acid
Molecular Structure
CAS Registry Number 3238-40-2
SynonymsFDCA; 2,5-Furandicarboxylic acid; Furan-2,5-dicarboxylic acid; 3238-40-2; Dehydromucic acid; Furan-2,5-dicarbonsaeure; 2,5-Furandicarboxylic acid
Molecular FormulaC6H4O5
Molecular Weight156.095
InChIInChI=1S/C6H4O5/c7-5(8)3-1-2-4(11-3)6(9)10/h1-2H,(H,7,8)(H,9,10)
InChI Key CHTHALBTIRVDBM-UHFFFAOYSA-N
Canonical SMILES C1=C(OC(=C1)C(=O)O)C(=O)O
Patent Information
Patent IDTitlePublication Date
CN108299357Method for preparing disubstituted furan compound2018
JP2017/1903162, 5 – furan dicarboxylic acid purification method (by machine translation)2017
WO2016/186504PROCESS FOR THE PREPARATION OF AN AROMATIC DICARBOXYLIC ACID2016
WO2016/202858PROCESSES FOR THE FORMATION OF FURANDICARBOXYLIC ACID (FDCA) VIA A MULTISTEP BIOCATALYTIC OXIDATION REACTION OF 5-HYDROXYMETHYLFURFURAL (HMF)2016
WO2015/60827METHODS AND COMPOUNDS FOR PRODUCING NYLON 6,62015
WO2014/65657PROCESS FOR THE PREPARATION OF BENZENE DERIVATIVES FROM FURAN DERIVATIVES2014
US2014/171663PROCESS FOR PRODUCING COMPOUNDS COMPRISING NITRILE FUNCTIONS2014
WO2013/49711METHODS FOR PREPARING 2,5-FURANDICARBOXYLIC ACID2013
US4327209Process for the production of dibenzazolyl compounds1982
US2003/176641Synthetic ion channels2003
US2012/2205072,5-FURAN DICARBOXYLATE DERIVATIVES, AND USE THEREOF AS PLASTICIZERS2012
WO2008/9735PYRAZOLO (3, 4-B) PYRIDINE DERIVATIVES AS PDE4 INHIBITORS2008
US44579241,1-Alkanediol dicarboxylate linked antibacterial agents1984

Physical Data

AppearanceUltra-white powder
Water SolubilitySlightly soluble(1.87e-02 g/L)
Melting Point340 – 345 °C
Sublimation320-322grad
Density1.73 g/cm3 at 20°C (68°F)
Water Solubility0.899 g/l at 20°C (68°F) – partly soluble
Partition Coefficient: Noctanol/Waterlog Pow: < -1.429 at 20°C (68°F)
Decomposition Temperature250°C (482°F) min
StabilityLight sensitive, very Hygroscopic

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °CFrequency (NMR Spectroscopy), MHz
Spectrum1H[D3]acetonitrile 24.94400
Chemical shifts, Spectrum1Hdimethylsulfoxide-d624.84250
Chemical shifts, Spectrum13Cdimethylsulfoxide-d626.8475.5
Chemical shifts 13Cdimethylsulfoxide-d624.84125
2,5-Furandicarboxylic acid CAS#: 3238-40-2 HNMR2,5-Furandicarboxylic acid CAS#: 3238-40-2 HNMR
2,5-Furandicarboxylic acid CAS#: 3238-40-2 CNMR2,5-Furandicarboxylic acid CAS#: 3238-40-2 CNMR
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Bandsnujol3250 – 1285 cm**(-1)
BandsKBr 3100 – 1420 cm**(-1)
Bandsnujol3300 – 1575 cm**(-1)
2,5-Furandicarboxylic acid CAS#: 3238-40-2 IR2,5-Furandicarboxylic acid CAS 3238-40-2 IR
Chromatographic dataOriginal string
HPLC (High performance liquid chromatography)20.7 min
HPLC (High performance liquid chromatography)(retention time at 37 min)
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nm
Absorption maximaethanol263
Absorption maximaH2O264
Description (Crystal Phase)Comment (Crystal Phase)
Crystal structure determinationβ=96 grad, a=4.97 Angstroem, b=16.69 Angstroem, c=3.66 Angstroem, n=2., aus dem Roentgen-Diagramm.

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 2,5-Furandicarboxylic acid CAS 3238-40-2
ConditionsYield
Stage #1: 2-furanoic acid With potassium carbonate; caesium carbonate In water Green chemistry
Stage #2: carbon dioxide at 260 – 285℃ under 6000.6 Torr for 24h Flow reactor Green chemistry
Stage #3: With hydrogenchloride In water pH=2 Reagent/catalyst Pressure Temperature Green chemistry
89%
Stage #1: 2-furanoic acid With potassium carbonate In water
Stage #2: carbon dioxide With potassium acetate; sodium acetate at 280℃ under 6000.6 Torr for 24h Autoclave

Experimental Procedure
Into a 100 ml flask, 1.12 g (10 mmol) of furancarboxylic acid, 0.7 g (5 mmol) of potassium carbonate, and 10 ml of water were successively added. The obtained aqueous solution of potassium furancarboxylate was clarified, and the aqueous solution was evaporated to dryness under reduced pressure to give a solid powder of potassium salt of white furfuric acid. In a 100 ml high temperature and high pressure autoclave, the above prepared potassium salt of furancarboxylate, anhydrous potassium carbonate 3.45 g (25 mmol), mixed potassium acetate and sodium acetate 5.0 g (the quality of potassium acetate and sodium acetate) were respectively added. The ratio is 1:1). After the addition, the air in the reaction vessel was replaced by carbon dioxide. Then, while maintaining a certain gas flow, the pressure of carbon dioxide was maintained at 0.8 MPa, and the reaction was carried out at 280 ° C for 24 hours, and the conversion rate was 95%. After the reaction is completed, 100 ml of deionized water is added to the reaction system to obtain a brown transparent solution. 0.2 g of activated carbon is added to the mother liquid, and the mixture is stirred at 50 ° C for 30 minutes, and filtered while hot, and the obtained colorless aqueous solution is hydrochloric acid. Acidification to a pH of about 2, a large amount of white precipitate formed, vacuum filtration, vacuum drying, and recrystallization from water to give pure 2,5-furandicarboxylic acid. The pure 2,5-furandicarboxylic acid prepared in Example 1 of the present invention was characterized, and the obtained 2,5-furandicarboxylic acid was subjected to nuclear magnetic resonance analysis using deuterated DMSO as a solvent. Referring to Fig. 1, Fig. 1 is a nuclear magnetic resonance spectrum of pure 2,5-furandicarboxylic acid prepared in Example 1 of the present invention. It can be seen from Fig. 1 that the pure 2,5-furandicarboxylic acid prepared by the invention has no obvious impurity peak, and the purity by NMR is ≥99%. The yield of the pure 2,5-furandicarboxylic acid prepared in Example 1 of the present invention was 80%.
80%
With sodium oxalate; potassium hydroxide at 280℃ under 75007.5 Torr for 8h Temperature Pressure Reagent/catalyst 76%
Stage #1: 2-furanoic acid With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane for 1.3h Inert atmosphere Sealed tube
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 – 0℃ for 0.5h Inert atmosphere Sealed tube
Stage #3: With hydrogenchloride In water at 80℃ for 2h Inert atmosphere Sealed tube
73%

Other Data

TransportationNot dangerous goods
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD 380/kg
Use Pattern
plasticizer
Monomer in a polymerisation process
Isolation from Natural Product
Phomopsis long (Deem.) Trav.
Occurrence and determination in excretion in the urine of humans before and after administration of Ca-gluconate, galactose or mesoinositol
from urine of humans

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Approved Manufacturers

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Ulcho Biochemical Ltdhttps://www.ulcho.com/
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