2,5-Dimethylfuran

2,5-Dimethylfuran

Names
IUPAC name 2,5-Dimethylfuran
Identifiers
CAS Number	625-86-5 Y
3D model (Jmol)	Interactive image Interactive image
ChemSpider	11763 Y
ECHA InfoCard	100.009.923
EC Number	210-914-3
PubChem	12266
UNII	DR5HL9OJ7Y Y
InChI InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 Y Key: GSNUFIFRDBKVIE-UHFFFAOYSA-N Y InChI=1/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 Key: GSNUFIFRDBKVIE-UHFFFAOYAS
SMILES o1c(ccc1C)C Cc1ccc(o1)C
Properties
Chemical formula	C6H8O
Molar mass	96.13
Appearance	Liquid
Density	0.8897 g/cm3
Melting point	−62 °C (−80 °F; 211 K)
Boiling point	92 to 94 °C (198 to 201 °F; 365 to 367 K)
Solubility in water	Insoluble
Magnetic susceptibility (χ)	-66.37·10−6 cm3/mol
Refractive index (nD)	1.44 - 1.442
Hazards
Main hazards	Very flammable, harmful
Flash point	−1 °C (30 °F; 272 K)
Autoignition temperature	285.85
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

2,5-Dimethylfuran is a heterocyclic compound with the formula (CH₃)₂C₄H₂O. Although often abbreviated DMF, it should not be confused with dimethylformamide. A derivative of furan, this simple compound is a potential biofuel, being derivable from cellulose.

Fructose can be converted into 2,5-dimethylfuran in a catalytic biomass-to-liquid process. The conversion of fructose to DMF proceeds via hydroxymethylfurfural.

Fructose is obtainable from glucose, a building block in cellulose.

DMF has a number of attractions as a biofuel. It has an energy density 40% greater than that of ethanol, making it comparable to gasoline (petrol). It is also chemically stable and, being insoluble in water, does not absorb moisture from the atmosphere. Evaporating dimethylfuran during the production process also requires around one third less energy than the evaporation of ethanol, although it has a boiling point some 14 °C higher, at 92 °C, compared to 78 °C for ethanol.

The ability to efficiently and rapidly produce dimethylfuran from fructose, found in fruit and some root vegetables, or from glucose, which can be derived from starch and cellulose - all widely available in nature - adds to the attraction of dimethylfuran, although safety issues must be examined. Bioethanol and biodiesel are currently the leading liquid biofuels.

The stoichiometric air/fuel ratio of dimethylfuran is 10.72, compared to ethanol at 8.95 and gasoline at 14.56. This means that burning dimethylfuran requires approximately 33% less air than the same quantity of gasoline, but approximately 20% more air than the same quantity of ethanol.