2,5-Dimethylfuran

changed 477211862 2,5-dimethylfuran.svg 180 px Skeletal formula 2,5-dimethylfuran other version.svg 180 px Space-filling model 2,5-Dimethylfuran correct chemspider 11763 89052 1/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 GSNUFIFRDBKVIE-UHFFFAOYAS Cc1ccc(o1)C correct chemspider 1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 correct chemspider GSNUFIFRDBKVIE-UHFFFAOYSA-N correct CAS 625-86-5 12266 correct FDA DR5HL9OJ7Y o1c(ccc1C)C 210-914-3 C6H8O 96.13 Liquid 0.8897 g/cm3 −62 92 to 94 Insoluble 1.44 – 1.442http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D14164&target=entry&action=PowerSearch&format=google2008 ChemExper chemical directory - Catalog of chemicals and suppliers 2011-03-17 2011-09-27 https://web.archive.org/web/20110927181802/http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID=14164&target=entry&action=PowerSearch&format=google2008 live −66.37·10−6 cm3/mol Very flammable, harmful −1 285.85 http://www.ecofriendlymag.com/sustainable-transporation-and-alternative-fuel/direct-injection-engine-study-finds-that-dmf-is-a-promising-biofuel-with-combustion-performance-and-regulated-emissions-comparable-to-gasoline/ Direct-Injection Engine Study Finds That DMF Is a Promising Biofuel, With Combustion Performance and Regulated Emissions Comparable to Gasoline | Eco Friendly dead https://archive.today/20130121205107/http://www.ecofriendlymag.com/sustainable-transporation-and-alternative-fuel/direct-injection-engine-study-finds-that-dmf-is-a-promising-biofuel-with-combustion-performance-and-regulated-emissions-comparable-to-gasoline/ 2013-01-21 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. 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. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates Yuriy Román-Leshkov Christopher J. Barrett Zhen Y. Liu James A. Dumesic Nature 2007 447 7147 982–5 10.1038/nature05923 17581580 2007Natur.447..982R 4366510 Fruit could make 'powerful fuel' Matt McGrath BBC News 2007-06-21 2007-06-22 https://news.bbc.co.uk/1/hi/sci/tech/6224846.stm 2007-08-17 live https://web.archive.org/web/20070817013407/http://news.bbc.co.uk/1/hi/sci/tech/6224846.stm Fructose is obtainable from glucose, a building block in cellulose. Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural Haibo Zhao Johnathan E. Holladay Heather Brown Z. Conrad Zhang Science June 15, 2007 316 5831 1597–1600 10.1126/science.1141199 17569858 2007Sci...316.1597Z 39295324 Plastic that grows on trees Pacific Northwest National Laboratory press release 2007-06-21 2007-06-22 http://www.pnl.gov/topstory.asp?id=255 https://web.archive.org/web/20070713174945/http://www.pnl.gov/topstory.asp?id=255 13 July 2007 dead 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, http://www.news.wisc.edu/13881 Engineers develop higher-energy liquid-transportation fuel from sugar James Beal University of Wisconsin-Madison press release 2007-06-20 2007-06-22 https://web.archive.org/web/20070701141451/http://www.news.wisc.edu/13881 1 July 2007 live 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. 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. The research octane number (RON) of dimethylfuran is 119. The latent heat of vaporization at 20 °C is 31.91 kJ/mol. Recent tests in a single-cylinder gasoline engine found that the thermal efficiency of burning dimethylfuran is similar to that of gasoline.http://www.greencarcongress.com/2010/05/directinjection-engine-study-finds-that-dmf-is-a-promising-biofuel-with-combustion-performance-and-r.html Green Car Congress: Direct-Injection Engine Study Finds That DMF Is a Promising Biofuel, With Combustion Performance and Regulated Emissions Comparable to Gasoline 2011-03-17 2011-12-24 https://web.archive.org/web/20111224050958/http://www.greencarcongress.com/2010/05/directinjection-engine-study-finds-that-dmf-is-a-promising-biofuel-with-combustion-performance-and-r.html live 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.Patrick L. Brezonik. Chemical Kinetics and Process Dynamics in Aquatic Systems. CRC Press, 1994, p. 671. https://web.archive.org/web/20200724194735/https://books.google.com/books?id=fzOHIweIZCsC&pg=RA4-PA671&dq=2,5-dimethylfuran&as_brr=3&sig=A0mQS0nmveWTmRiRbzeBbaNayu0#PRA4-PA671,M1 2020-07-24 750px 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.S. W. Gerritz A. M. Sefler 2,5-Dimethylfuran (DMFu): An Internal Standard for the "Traceless" Quantitation of Unknown Samples via 1H NMR 2000 J. Comb. Chem. 2 1 39–41 10.1021/cc990041v 10813883 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. 10.2307/3430317 W.D. Powrie C.H. Wu V.P. Molund Browning reaction systems as sources of mutagens and antimutagens Environmental Health Perspectives 1986 67 47–54 1474410 3757959 3430317 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.Peter Arlien-Søborg. Solvent Neurotoxicity. CRC Press, 1992. 0-8493-6234-2. https://web.archive.org/web/20210221202114/https://books.google.com/?pg=RA3-PA212&ots=clFo1K-pB-&dq=2,5-Dimethylfuran&as_brr=3&sig=eddaKIeD7FmzpupK_xKwJvC3gK0&hl=en#PRA3-PA212,M1 2021-02-21 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).Donald Shopland. Cigars: Health Effects and Trends. DIANE Publishing, 1998. https://web.archive.org/web/20200724201017/https://books.google.com/books?id=5KVvx8kNhXYC&pg=PA88&ots=7peGM2UGhA&dq=2,5-Dimethylfuran&as_brr=1&sig=Jrp4Eo5t4neA-j-iM06WUp51RTo#PPA88,M1 2020-07-24 Its blood concentration can be used as a biomarker for smoking. 10.1007/BF00381629 8919847 Using the blood concentration of 2,5-dimethylfuran as a marker for smoking 1996 Ashley D. L. Bonin M. A. Hamar B. McGeehin M. International Archives of Occupational and Environmental Health 68 3 183–7 1996IAOEH..68..183A 22233967 https://zenodo.org/record/1232436 2020-09-12 2021-02-21 https://web.archive.org/web/20210221202120/https://zenodo.org/record/1232436 live Comparison of Safety Data Sheets shows that human handling of 2,5-dimethylfuranhttp://www.fishersci.com/ecomm/servlet/msdsproxy?productName=AC176031000&productDescription=dimethylfuran--acros-organics&catNo=AC176031000&vendorId=VN00032119&storeId=10652 Safety Data Sheet: 2,5-Dimethylfuran Thermo Fisher Scientific 2014-03-07 2014-03-07 https://web.archive.org/web/20140307184050/http://www.fishersci.com/ecomm/servlet/msdsproxy?productName=AC176031000&productDescription=dimethylfuran--acros-organics&catNo=AC176031000&vendorId=VN00032119&storeId=10652 dead http://www.chemicalbook.com/ProductMSDSDetailCB2854009_EN.htm 2,5-Dimethylfuran(625-86-5) Chemical Book 2017-07-21 2017-05-04 https://web.archive.org/web/20170504000607/http://www.chemicalbook.com/ProductMSDSDetailCB2854009_EN.htm live http://www.t3db.ca/system/msds/attachments/000/001/956/original/T3D3982.pdf?1414204247 Material Safety Data Sheet 2,5-Dimethylfuran 6 January 2012 live https://web.archive.org/web/20220804123757/http://www.t3db.ca/system/msds/attachments/000/001/956/original/T3D3982.pdf?1414204247 4 August 2022 is approximately as hazardous as handling gasoline.http://www.equivashellmsds.com/getsinglemsds.asp?ID=202020 Equiva Services - MSDS dead https://web.archive.org/web/20110710195308/http://www.equivashellmsds.com/getsinglemsds.asp?ID=202020 2011-07-10 http://hazard.com/msds/f2/bxw/bxwzb.html hazard.com 2010-12-27 2011-07-11 https://web.archive.org/web/20110711151929/http://hazard.com/msds/f2/bxw/bxwzb.html usurped http://hazard.com/msds/f2/bhh/bhhfm.html hazard.com 2010-12-27 2011-07-11 https://web.archive.org/web/20110711151934/http://hazard.com/msds/f2/bhh/bhhfm.html usurped References Energy 2 Category:Furans Category:Biofuels