2,5-Furandicarboxylic acid CAS#: 3238-40-2; ChemWhat Code: 25627
Identification
| Product Name | 2,5-Furandicarboxylic acid |
| Molecular Structure |  |
| CAS Registry Number | 3238-40-2 |
| Synonyms | FDCA; 2,5-Furandicarboxylic acid; Furan-2,5-dicarboxylic acid; 3238-40-2; Dehydromucic acid; Furan-2,5-dicarbonsaeure; 2,5-Furandicarboxylic acid |
| Molecular Formula | C6H4O5 |
| Molecular Weight | 156.095 |
| InChI | InChI=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 |
Physical Data
| Appearance | Ultra-white powder |
| Water Solubility | Slightly soluble(1.87e-02 g/L) |
| Melting Point | 340 – 345 °C |
| Sublimation | 320-322grad |
| Density | 1.73 g/cm3 at 20°C (68°F) |
| Water Solubility | 0.899 g/l at 20°C (68°F) – partly soluble |
| Partition Coefficient: Noctanol/Water | log Pow: < -1.429 at 20°C (68°F) |
| Decomposition Temperature | 250°C (482°F) min |
| Stability | Light sensitive, very Hygroscopic |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Spectrum | 1H | [D3]acetonitrile | 24.94 | 400 |
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 24.84 | 250 |
| Chemical shifts, Spectrum | 13C | dimethylsulfoxide-d6 | 26.84 | 75.5 |
| Chemical shifts | 13C | dimethylsulfoxide-d6 | 24.84 | 125 |
| 2,5-Furandicarboxylic acid CAS#: 3238-40-2 HNMR |  |
| 2,5-Furandicarboxylic acid CAS#: 3238-40-2 CNMR |  |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Comment (IR Spectroscopy) |
| Bands | nujol | 3250 – 1285 cm**(-1) |
| Bands | KBr | 3100 – 1420 cm**(-1) |
| Bands | nujol | 3300 – 1575 cm**(-1) |
| 2,5-Furandicarboxylic acid CAS#: 3238-40-2 IR |  |
| Chromatographic data | Original 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 maxima | ethanol | 263 |
| Absorption maxima | H2O | 264 |
| Description (Crystal Phase) | Comment (Crystal Phase) |
| Crystal structure determination | β=96 grad, a=4.97 Angstroem, b=16.69 Angstroem, c=3.66 Angstroem, n=2., aus dem Roentgen-Diagramm. |
Route of Synthesis (ROS)
| Conditions | Yield |
| 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
| Transportation | Not dangerous goods |
| Under the room temperature and away from light | |
| HS Code | 294200 |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD 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 |
Buy Reagent | |
| Sigma-Aldrich 722081 | 5g, 97% |
| ChemWhat 25627 | 10g, 50g, 100g, 200g, 250g, 500g, 99% |
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Approved Manufacturers | |
| Avantium | https://www.avantium.com/ |
| Ulcho Biochemical Ltd | https://www.ulcho.com/ |
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