2,5-Dimethylfuran

Last updated
2,5-Dimethylfuran
2,5-dimethylfuran.svg
2,5-dimethylfuran other version.svg
Names
Preferred IUPAC name
2,5-Dimethylfuran
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.923 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-914-3
PubChem CID
UNII
  • InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 Yes check.svgY
    Key: GSNUFIFRDBKVIE-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
    Key: GSNUFIFRDBKVIE-UHFFFAOYAS
  • o1c(ccc1C)C
  • Cc1ccc(o1)C
Properties
C6H8O
Molar mass 96.13
AppearanceLiquid
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)
Insoluble
-66.37·10−6 cm3/mol
1.44 – 1.442 [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Very flammable, harmful
Flash point −1 °C (30 °F; 272 K) [1]
285.85 °C (546.53 °F; 559.00 K) [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Production

Fructose can be converted into 2,5-dimethylfuran in a catalytic biomass-to-liquid process. The conversion of fructose to DMF proceeds via hydroxymethylfurfural. [3] [4]

Fructose is obtainable from glucose, a building block in cellulose. [5] [6]

Potential as a biofuel

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, [3] [7] 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. [2] 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.

The calorific value of liquid dimethylfuran is 33.7 MJ/kg, compared to 26.9 MJ/kg for ethanol and 43.2 MJ/kg for gasoline. [2] The research octane number (RON) of dimethylfuran is 119. [2] The latent heat of vaporization at 20 °C is 31.91 kJ/mol. [2] Recent tests in a single-cylinder gasoline engine found that the thermal efficiency of burning dimethylfuran is similar to that of gasoline. [8]

Other uses

2,5-Dimethylfuran serves 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. [9] Dimethylfuran reaction with singlet oxygen.png

2,5-Dimethylfuran has also been proposed as an internal standard for NMR spectroscopy. 2,5-Dimethylfuran has singlets in its 1H NMR spectrum at δ 2.2 and 5.8; the singlets give reliable integrations, while the positions of the peaks do not interfere with many analytes. The compound also has an appropriate boiling point of 92 °C which prevents evaporative losses, yet is easily removed. [10]

Role in food chemistry

2,5-Dimethylfuran forms upon thermal degradation of some sugars and has been identified in trace amounts as a component of caramelized sugars. [11]

Toxicology

2,5-Dimethylfuran plays a role in the mechanism for the neurotoxicity of hexane in humans. Together with hexane-2,5-dione and 4,5-dihydroxy-2-hexanone, it is one of the main metabolites of hexane. [12]

2,5-Dimethylfuran has been identified as one of the components of cigar smoke with low ciliary toxicity (ability to adversely affect the cilia in the respiratory tract that are responsible for removing foreign particles). [13] Its blood concentration can be used as a biomarker for smoking. [14]

Comparison of Safety Data Sheets shows that human handling of 2,5-dimethylfuran [15] [16] [17] is approximately as hazardous as handling gasoline. [18] [19] [20]

Related Research Articles

<span class="mw-page-title-main">Biofuel</span> Type of biological fuel produced from biomass from which energy is derived

Biofuel is a fuel that is produced over a short time span from biomass, rather than by the very slow natural processes involved in the formation of fossil fuels such as oil. Biofuel can be produced from plants or from agricultural, domestic or industrial biowaste. Biofuels are mostly used for transportation, but can also be used for heating and electricity. Biofuels are regarded as a renewable energy source. The use of biofuel has been subject to criticism regarding the "food vs fuel" debate, varied assessments of their sustainability, and possible deforestation and biodiversity loss as a result of biofuel production.

<span class="mw-page-title-main">Ethanol fuel</span> Type of biofuel

Ethanol fuel is fuel containing ethyl alcohol, the same type of alcohol as found in alcoholic beverages. It is most often used as a motor fuel, mainly as a biofuel additive for gasoline.

Cellulosic ethanol is ethanol produced from cellulose rather than from the plant's seeds or fruit. It can be produced from grasses, wood, algae, or other plants. It is generally discussed for use as a biofuel. The carbon dioxide that plants absorb as they grow offsets some of the carbon dioxide emitted when ethanol made from them is burned, so cellulosic ethanol fuel has the potential to have a lower carbon footprint than fossil fuels.

<span class="mw-page-title-main">Iogen Corporation</span>

Iogen Corporation is a Canadian company based in Ottawa, Ontario, Canada, and was founded by Patrick Foody Sr. in 1975.

<span class="mw-page-title-main">Biomass to liquid</span>

Biomass to liquid is a multi-step process of producing synthetic hydrocarbon fuels made from biomass via a thermochemical route.

<span class="mw-page-title-main">Hydroxymethylfurfural</span> Chemical compound

Hydroxymethylfurfural (HMF), also known as 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid which is highly soluble in both water and organic solvents. The molecule consists of a furan ring, containing both aldehyde and alcohol functional groups.

<span class="mw-page-title-main">Alcohol fuel</span>

Various alcohols are used as fuel for internal combustion engines. The first four aliphatic alcohols are of interest as fuels because they can be synthesized chemically or biologically, and they have characteristics which allow them to be used in internal combustion engines. The general chemical formula for alcohol fuel is CnH2n+1OH.

<span class="mw-page-title-main">Ethanol fuel in Brazil</span>

Brazil is the world's second largest producer of ethanol fuel. Brazil and the United States have led the industrial production of ethanol fuel for several years, together accounting for 85 percent of the world's production in 2017. Brazil produced 26.72 billion liters, representing 26.1 percent of the world's total ethanol used as fuel in 2017.

<span class="mw-page-title-main">Bioconversion of biomass to mixed alcohol fuels</span>

The bioconversion of biomass to mixed alcohol fuels can be accomplished using the MixAlco process. Through bioconversion of biomass to a mixed alcohol fuel, more energy from the biomass will end up as liquid fuels than in converting biomass to ethanol by yeast fermentation.

<span class="mw-page-title-main">Lignocellulosic biomass</span> Plant dry matter

Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose and hemicellulose, and an aromatic-rich polymer called lignin. Any biomass rich in cellulose, hemicelluloses, and lignin are commonly referred to as lignocellulosic biomass. Each component has a distinct chemical behavior. Being a composite of three very different components makes the processing of lignocellulose challenging. The evolved resistance to degradation or even separation is referred to as recalcitrance. Overcoming this recalcitrance to produce useful, high value products requires a combination of heat, chemicals, enzymes, and microorganisms. These carbohydrate-containing polymers contain different sugar monomers and they are covalently bound to lignin.

The United States produces mainly biodiesel and ethanol fuel, which uses corn as the main feedstock. The US is the world's largest producer of ethanol, having produced nearly 16 billion gallons in 2017 alone. The United States, together with Brazil accounted for 85 percent of all ethanol production, with total world production of 27.05 billion gallons. Biodiesel is commercially available in most oilseed-producing states. As of 2005, it was somewhat more expensive than fossil diesel, though it is still commonly produced in relatively small quantities.

<span class="mw-page-title-main">Butanol fuel</span> Fuel for internal combustion engines

Butanol may be used as a fuel in an internal combustion engine. It is more similar to gasoline than it is to ethanol. A C4-hydrocarbon, butanol is a drop-in fuel and thus works in vehicles designed for use with gasoline without modification. Both n-butanol and isobutanol have been studied as possible fuels. Both can be produced from biomass (as "biobutanol" ) as well as from fossil fuels (as "petrobutanol"). The chemical properties depend on the isomer (n-butanol or isobutanol), not on the production method.

Renewable Fuels are fuels produced from renewable resources. Examples include: biofuels, Hydrogen fuel, and fully synthetic fuel produced from ambient carbon dioxide and water. This is in contrast to non-renewable fuels such as natural gas, LPG (propane), petroleum and other fossil fuels and nuclear energy. Renewable fuels can include fuels that are synthesized from renewable energy sources, such as wind and solar. Renewable fuels have gained in popularity due to their sustainability, low contributions to the carbon cycle, and in some cases lower amounts of greenhouse gases. The geo-political ramifications of these fuels are also of interest, particularly to industrialized economies which desire independence from Middle Eastern oil.

Second-generation biofuels, also known as advanced biofuels, are fuels that can be manufactured from various types of non-food biomass. Biomass in this context means plant materials and animal waste used especially as a source of fuel.

γ-Valerolactone Chemical compound

γ-Valerolactone (GVL) or gamma-valerolactone is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones. GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.

Biogasoline is a type of gasoline produced from biomass such as algae. Like traditionally produced gasoline, it is made up of hydrocarbons with 6 (hexane) to 12 (dodecane) carbon atoms per molecule and can be used in internal combustion engines. However, unlike traditional gasoline/petroleum based fuels, which are mainly composed from oil, biogasolines are made from plants such as beets and sugarcane or cellulosic biomass- substances normally referred to as plant waste.

<span class="mw-page-title-main">Sustainable biofuel</span> Non-fossil-based sustainable production

Sustainable biofuel is biofuel produced in a sustainable manner. It is not based on petroleum or other fossil fuels. It includes not using plants that are used for food stuff to produce the fuel thus disrupting the world's food supply.

Issues relating to biofuel are social, economic, environmental and technical problems that may arise from biofuel production and use. Social and economic issues include the "food vs fuel" debate and the need to develop responsible policies and economic instruments to ensure sustainable biofuel production. Farming for biofuels feedstock can be detrimental to the environment if not done sustainably. Environmental concerns include deforestation, biodiversity loss and soil erosion as a result of land clearing for biofuels agriculture. While biofuels can contribute to reduction in global carbon emissions, indirect land use change for biofuel production can have the inverse effect. Technical issues include possible modifications necessary to run the engine on biofuel, as well as energy balance and efficiency.

<span class="mw-page-title-main">2,5-Bis(hydroxymethyl)furan</span> Chemical compound

2,5-Bis(hydroxymethyl)furan (BHMF) is a heterocyclic organic compound, and is a derivative of a broader class of compounds known as furans. It is produced from cellulose and has received attention as a biofeedstock. It is a white solid, although commercial samples can appear yellowish or tan.

<span class="mw-page-title-main">Methoxymethylfurfural</span> Chemical compound

Methoxymethylfurfural is an organic compound derived from dehydration of sugars and subsequent etherification with methanol. This colorless liquid is soluble in a wide range of solvents including lower alcohols. The molecule is a derivative of furan, containing both aldehyde and ether (methoxymethyl) functional groups. MMF has been detected in the leaves and roots of Chilean Jaborosa magellanica (Solanaceae). It has a typical odor suggestive of maraschino cherries. MMF can be made from a wide range of carbohydrate containing feedstocks including sugar, starch and cellulose using a chemical catalytic process and is a potential "carbon-neutral" feedstock for fuels and chemicals.

References

  1. 1 2 "ChemExper chemical directory - Catalog of chemicals and suppliers". Archived from the original on 2011-09-27. Retrieved 2011-03-17.
  2. 1 2 3 4 5 "Direct-Injection Engine Study Finds That DMF Is a Promising Biofuel, With Combustion Performance and Regulated Emissions Comparable to Gasoline | Eco Friendly". Archived from the original on 2013-01-21.
  3. 1 2 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): 982–5. Bibcode:2007Natur.447..982R. doi:10.1038/nature05923. PMID   17581580. S2CID   4366510.
  4. ↑ Matt McGrath (2007-06-21). "Fruit could make 'powerful fuel'". BBC News. Archived from the original on 2007-08-17. Retrieved 2007-06-22.
  5. ↑ Haibo Zhao; Johnathan E. Holladay; Heather Brown; Z. Conrad Zhang (June 15, 2007). "Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural". Science . 316 (5831): 1597–1600. Bibcode:2007Sci...316.1597Z. doi:10.1126/science.1141199. PMID   17569858. S2CID   39295324.
  6. ↑ "Plastic that grows on trees". Pacific Northwest National Laboratory. 2007-06-21. Archived from the original (press release) on 13 July 2007. Retrieved 2007-06-22.
  7. ↑ James Beal (2007-06-20). "Engineers develop higher-energy liquid-transportation fuel from sugar" (press release). University of Wisconsin-Madison. Archived from the original on 1 July 2007. Retrieved 2007-06-22.
  8. ↑ "Green Car Congress: Direct-Injection Engine Study Finds That DMF Is a Promising Biofuel, With Combustion Performance and Regulated Emissions Comparable to Gasoline". Archived from the original on 2011-12-24. Retrieved 2011-03-17.
  9. ↑ Patrick L. Brezonik. Chemical Kinetics and Process Dynamics in Aquatic Systems. CRC Press, 1994, p. 671. Archived 2020-07-24 at the Wayback Machine
  10. ↑ S. W. Gerritz; 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. PMID   10813883.
  11. ↑ 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. JSTOR   3430317. PMC   1474410 . PMID   3757959.
  12. ↑ Peter Arlien-Søborg. Solvent Neurotoxicity. CRC Press, 1992. ISBN   0-8493-6234-2. Archived 2021-02-21 at the Wayback Machine
  13. ↑ Donald Shopland. Cigars: Health Effects and Trends. DIANE Publishing, 1998. Archived 2020-07-24 at the Wayback Machine
  14. ↑ Ashley, D. L.; Bonin, M. A.; Hamar, B.; McGeehin, M. (1996). "Using the blood concentration of 2,5-dimethylfuran as a marker for smoking". International Archives of Occupational and Environmental Health. 68 (3): 183–7. Bibcode:1996IAOEH..68..183A. doi:10.1007/BF00381629. PMID   8919847. S2CID   22233967. Archived from the original on 2021-02-21. Retrieved 2020-09-12.
  15. ↑ "Safety Data Sheet: 2,5-Dimethylfuran". Thermo Fisher Scientific. Archived from the original on 2014-03-07. Retrieved 2014-03-07.
  16. ↑ "2,5-Dimethylfuran(625-86-5)". Chemical Book. Archived from the original on 2017-05-04. Retrieved 2017-07-21.
  17. ↑ "Material Safety Data Sheet 2,5-Dimethylfuran" (PDF). 6 January 2012. Archived (PDF) from the original on 4 August 2022.
  18. ↑ "Equiva Services - MSDS". Archived from the original on 2011-07-10.
  19. ↑ "hazard.com". Archived from the original on 2011-07-11. Retrieved 2010-12-27.{{cite web}}: CS1 maint: unfit URL (link)
  20. ↑ "hazard.com". Archived from the original on 2011-07-11. Retrieved 2010-12-27.{{cite web}}: CS1 maint: unfit URL (link)
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