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2,5-Dimethylfuran



2,5-Dimethylfuran
Identifiers
CAS number 625-86-5
PubChem 12266
EINECS number 210-914-3
SMILES Cc1ccc(C)o1
Properties
Molecular formula C6H8O
Molar mass 96.13
Appearance Liquid
Density 0.9 g/mL
Melting point

−62 °C

Boiling point

92–94 °C

Solubility in water Insoluble
Hazards
Main hazards Very flammable, harmful
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

2,5-Dimethylfuran is a heterocyclic compound of the formula C6H8O. A derivative of furan, it is also known by its abbreviation DMF, not to be confused with dimethylformamide. Recent advances have increased its attractiveness as a biofuel.

Additional recommended knowledge

Contents

Production

Recent research has resulted in improved and more efficient production methods that convert fructose or glucose to a key building block of 2,5-dimethylfuran - hydroxymethylfurfural - in a catalytic biomass-to-liquid process.

Research into an acid catalyst method, undertaken by scientists from the University of Wisconsin-Madison, was published in Science on June 30, 2006,[1] and in Nature on June 21, 2007.[2][3]

Another team from Pacific Northwest National Laboratory have developed a non-acidic catalytic method, reported in Science on June 15, 2007.[4][5] Although it produces a lower yield, glucose can also be used in the processes.

Potential as a biofuel

DMF has a number of attractions as a biofuel. It has an energy density 40% greater than 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,[6][2] 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 - is likely to add to the attraction of dimethylfuran once safety issues have been examined. Bioethanol and biodiesel are currently the leading liquid biofuels.

Other uses

2,5-Dimethylfuran acts as a scavenger for singlet oxygen, a property which has been exploited for the determination of singlet oxygen in natural waters. The mechanism involves a Diels-Alder reaction followed by hydrolysis, ultimately leading to diacetylethylene and hydrogen peroxide as products. More recently, furfuryl alcohol has been used for the same purpose.[7]


This compound has also been proposed as an internal standard for NMR spectroscopy. This is due to its good intrinsic properties. 2,5-Dimethylfuran has two singlets in its NMR spectrum at δ 2.2 and 5.8; the singlets give reliable integrations, while the positions of the peaks do not interfere with most analytes. The compound also has an appropriate boiling point of 92 °C which prevents evaporative losses, yet is easily removed.[8]

Toxicology

2,5-Dimethylfuran, together with 2,5-hexanedione and 4,5-dihydroxy-2-hexanone, is one of the main metabolites of hexane in humans, which play a role in the mechanism for the neurotoxicity of hexane.[9]

2,5-Dimethylfuran has been identified as one of the components of cigar smoke with low cilatoxicity (ability to adversely affect the cilia in the respiratory tract that are responsible for removing foreign particles). [10] Its blood concentration can be used as a biomarker for smoking.[11]

Role in food chemistry

2,5-Dimethylfuran can be formed from the thermal degradation of sugars, and has been identified in trace amounts as a component of caramelized sugars.[12]

References

Energy Portal
  1. ^ James Beal (2006-06-29). New process makes diesel fuel, industrial chemicals from simple sugar (press release). University of Wisconsin-Madison. Retrieved on 2007-06-22.
  2. ^ a b Yuriy Román-Leshkov, Christopher J. Barrett, Zhen Y. Liu & James A. Dumesic (2007). "Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates". Nature 447 (7147): 982. doi:10.1038/nature05923.
  3. ^ Matt McGrath. "Fruit could make 'powerful fuel'", BBC News, 21 Jun 2007. Retrieved on 2007-06-22. 
  4. ^ Haibo Zhao, Johnathan E. Holladay, Heather Brown, Z. Conrad Zhang (June 15). "Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural". Science 316 (5831): 1597 - 1600. doi:10.1126/science.1141199.
  5. ^ "Plastic that grows on trees" (press release), Pacific Northwest National Laboratory, 21 Jun 2007. Retrieved on 2007-06-22. 
  6. ^ James Beal (2007-06-20). Engineers develop higher-energy liquid-transportation fuel from sugar (press release). University of Wisconsin-Madison. Retrieved on 2007-06-22.
  7. ^ Patrick L. Brezonik. Chemical Kinetics and Process Dynamics in Aquatic Systems. CRC Press, 1994, p. 671. [1]
  8. ^ S. W. Gerritz and A. M. Sefler (2000). "2,5-Dimethylfuran (DMFu): An Internal Standard for the "Traceless" Quantitation of Unknown Samples via 1H NMR". J. Comb. Chem 2 (1): 39-41. doi:10.1021/cc990041v.
  9. ^ Peter Arlien-Søborg. Solvent Neurotoxicity. CRC Press, 1992. ISBN 0849362342. [2]
  10. ^ Donald Shopland. Cigars: Health Effects and Trends. DIANE Publishing, 1998. [3]
  11. ^ D. L. Ashley, M. A. Bonin, B. Hamar, M. McGeehin. Using the blood concentration of 2,5-dimethylfuran as a marker for smoking. International Archives of Occupational and Environmental Health 1996, 68, 183-187. doi:10.1007/BF00381629
  12. ^ W.D. Powrie, C.H. Wu, V.P. Molund (1986). "Browning Reaction Systems as Sources of Mutagens and Antimutagens". Environmental Health Perspectives 67: 47-54. doi:10.2307/3430317.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "2,5-Dimethylfuran". A list of authors is available in Wikipedia.
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