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Revision as of 17:08, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465591265 of page 2,5-Dimethylfuran for the Chem/Drugbox validation project (updated: '').  Latest revision as of 22:38, 4 April 2024 edit ClumsyOwlet (talk | contribs)Extended confirmed users4,643 editsm Oops, or whenever the above section was removed 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Watchedfields = changed |Watchedfields = changed
| verifiedrevid = 443346019 |verifiedrevid = 477211862
| ImageFile1 = 2,5-dimethylfuran.svg |ImageFile1 = 2,5-dimethylfuran.svg
| ImageSize1 = 180 px |ImageSize1 = 180 px
| ImageName1 = Skeletal formula |ImageName1 = Skeletal formula
| ImageFile2 = 2,5-dimethylfuran other version.svg |ImageFile2 = 2,5-dimethylfuran other version.svg
| ImageSize2 = 180 px |ImageSize2 = 180 px
| ImageName2 = Space-filling model |ImageName2 = Space-filling model
| IUPACName = 2,5-Dimethylfuran |PIN = 2,5-Dimethylfuran
|Section1={{Chembox Identifiers
| OtherNames =
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Section1 = {{Chembox Identifiers
|ChemSpiderID = 11763
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChEBI = 89052
| ChemSpiderID = 11763
| InChI = 1/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 |InChI = 1/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
| InChIKey = GSNUFIFRDBKVIE-UHFFFAOYAS |InChIKey = GSNUFIFRDBKVIE-UHFFFAOYAS
| SMILES1 = Cc1ccc(o1)C |SMILES1 = Cc1ccc(o1)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 |StdInChI = 1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = GSNUFIFRDBKVIE-UHFFFAOYSA-N |StdInChIKey = GSNUFIFRDBKVIE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} |CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 625-86-5 |CASNo = 625-86-5
| PubChem = 12266 |PubChem = 12266
| UNII_Ref = {{fdacite|correct|FDA}} |UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DR5HL9OJ7Y |UNII = DR5HL9OJ7Y
| SMILES = o1c(ccc1C)C |SMILES = o1c(ccc1C)C
| EINECS = 210-914-3 |EINECS = 210-914-3
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>6</sub>H<sub>8</sub>O
| MolarMass = 96.13
| Appearance = Liquid
| Density = 0.8897 g/cm<sup>3</sup>
| MeltingPt = −62&nbsp;°C
| BoilingPt = 92–94&nbsp;°C
| Solubility = Insoluble
| RefractIndex = 1.44 - 1.442<ref name="chemexper1">http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D14164&target=entry&action=PowerSearch&format=google2008</ref>
}}
| Section3 = {{Chembox Hazards
| MainHazards = Very flammable, harmful
| FlashPt = −1&nbsp;°C<ref name="chemexper1"></ref>
| Autoignition = 285.85<ref name="directinjection">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/</ref>
}}
}} }}
|Section2={{Chembox Properties
|Formula = C<sub>6</sub>H<sub>8</sub>O
|MolarMass = 96.13
|Appearance = Liquid
|Density = 0.8897 g/cm<sup>3</sup>
|MeltingPtC = −62
|BoilingPtC = 92 to 94
|Solubility = Insoluble
|RefractIndex = 1.44 &ndash; 1.442<ref name="chemexper1">{{cite web |url=http://www.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?query=entry._entryID%3D14164&target=entry&action=PowerSearch&format=google2008 |title=ChemExper chemical directory - Catalog of chemicals and suppliers |access-date=2011-03-17 |archive-date=2011-09-27 |archive-url=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 |url-status=live }}</ref>
|MagSus = -66.37·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
|Section3={{Chembox Hazards
|MainHazards = Very flammable, harmful
|FlashPtC = −1
|FlashPt_ref = <ref name="chemexper1" />
|AutoignitionPtC = 285.85
|AutoignitionPt_ref = <ref name="directinjection">{{cite web|url=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/ |title=Direct-Injection Engine Study Finds That DMF Is a Promising Biofuel, With Combustion Performance and Regulated Emissions Comparable to Gasoline &#124; Eco Friendly |url-status=dead |archiveurl=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/ |archivedate=2013-01-21 }}</ref>
}}
}}

'''2,5-Dimethylfuran''' is a ] with the ] (CH<sub>3</sub>)<sub>2</sub>C<sub>4</sub>H<sub>2</sub>O. Although often abbreviated '''DMF''', it should not be confused with ]. A derivative of ], this simple compound is a potential ], being derivable from cellulose.

==Production==
] can be converted into 2,5-dimethylfuran in a ] ] process. The conversion of fructose to DMF proceeds via ].<ref name="nature05923">{{cite journal
| title = Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates
|author1=Yuriy Román-Leshkov |author2=Christopher J. Barrett |author3=Zhen Y. Liu |author4=James A. Dumesic | journal = ]| year = 2007| volume = 447| issue = 7147| pages = 982–5| doi = 10.1038/nature05923| pmid = 17581580|bibcode=2007Natur.447..982R |s2cid=4366510}}</ref><ref>{{cite news| title = Fruit could make 'powerful fuel'| author = Matt McGrath| publisher = ]| date = 2007-06-21| accessdate = 2007-06-22| url = http://news.bbc.co.uk/1/hi/sci/tech/6224846.stm| archive-date = 2007-08-17| archive-url = https://web.archive.org/web/20070817013407/http://news.bbc.co.uk/1/hi/sci/tech/6224846.stm}}</ref>

Fructose is obtainable from glucose, a building block in cellulose.<ref>{{cite journal
| title = Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural
|author1=Haibo Zhao |author2=Johnathan E. Holladay |author3=Heather Brown |author4=Z. Conrad Zhang |journal = ]| date = June 15, 2007| volume = 316| issue = 5831| pages = 1597–1600| doi = 10.1126/science.1141199| pmid = 17569858|bibcode=2007Sci...316.1597Z |s2cid=39295324}}</ref><ref>{{cite news| title = Plastic that grows on trees| publisher = Pacific Northwest National Laboratory| format = press release| date = 2007-06-21| accessdate = 2007-06-22| url = http://www.pnl.gov/topstory.asp?id=255| archiveurl = https://web.archive.org/web/20070713174945/http://www.pnl.gov/topstory.asp?id=255| archivedate= 13 July 2007 <!--DASHBot-->| url-status= dead}}</ref>

==Potential as a biofuel==
DMF has a number of attractions as a ]. It has an ] 40% greater than that of ], making it comparable to ] (petrol). It is also chemically stable and, being ] in water, does not absorb moisture from the atmosphere. ] dimethylfuran during the production process also requires around one third less energy than the evaporation of ethanol,<ref name="nature05923" /><ref>{{cite web
| url = http://www.news.wisc.edu/13881
| title = Engineers develop higher-energy liquid-transportation fuel from sugar
| author = James Beal
| publisher = University of Wisconsin-Madison
| format = press release
| date = 2007-06-20
| accessdate = 2007-06-22
| archiveurl = https://web.archive.org/web/20070701141451/http://www.news.wisc.edu/13881| archivedate= 1 July 2007 <!--DASHBot-->| url-status= live}}</ref> although it has a boiling point some 14&nbsp;°C higher, at 92&nbsp;°C, compared to 78&nbsp;°C for ethanol.

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

The ] of dimethylfuran is 10.72, compared to ethanol at 8.95 and gasoline at 14.56.<ref name="directinjection" /> 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 ] of liquid dimethylfuran is 33.7 MJ/kg, compared to 26.9 MJ/kg for ethanol and 43.2 MJ/kg for gasoline.<ref name="directinjection" /> The ] (RON) of dimethylfuran is 119.<ref name="directinjection" /> The ] at 20&nbsp;°C is 31.91 kJ/mol.<ref name="directinjection" /> Recent tests in a single-cylinder gasoline engine found that the thermal efficiency of burning dimethylfuran is similar to that of gasoline.<ref name="greencarcongress1">{{cite web |url=http://www.greencarcongress.com/2010/05/directinjection-engine-study-finds-that-dmf-is-a-promising-biofuel-with-combustion-performance-and-r.html |title=Green Car Congress: Direct-Injection Engine Study Finds That DMF Is a Promising Biofuel, With Combustion Performance and Regulated Emissions Comparable to Gasoline |access-date=2011-03-17 |archive-date=2011-12-24 |archive-url=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 |url-status=live }}</ref>

==Other uses==
2,5-Dimethylfuran serves as a ] for ], a property which has been exploited for the determination of singlet oxygen in natural waters. The mechanism involves a ] followed by ], ultimately leading to ] and ] as products. More recently, ] has been used for the same purpose.<ref>Patrick L. Brezonik. ''Chemical Kinetics and Process Dynamics in Aquatic Systems''. CRC Press, 1994, p. 671. {{Webarchive|url=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 |date=2020-07-24 }}</ref>
]

2,5-Dimethylfuran has also been proposed as an ] for ]. 2,5-Dimethylfuran has singlets in its <sup>1</sup>H 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&nbsp;°C which prevents evaporative losses, yet is easily removed.<ref>{{cite journal |author1=S. W. Gerritz |author2=A. M. Sefler | title = 2,5-Dimethylfuran (DMFu): An Internal Standard for the "Traceless" Quantitation of Unknown Samples via 1H NMR | year = 2000 | journal = ] | volume = 2 | issue = 1 | pages = 39–41 | doi = 10.1021/cc990041v|pmid=10813883 }}</ref>

==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 ] sugars.<ref>{{cite journal | doi = 10.2307/3430317 |author1=W.D. Powrie |author2=C.H. Wu |author3=V.P. Molund | title = Browning reaction systems as sources of mutagens and antimutagens | journal = ] | year = 1986 | volume = 67 | pages = 47–54 | pmc = 1474410 | pmid=3757959 | jstor=3430317}}</ref>

==Toxicology==
2,5-Dimethylfuran plays a role in the mechanism for the ] of hexane in humans. Together with ] and 4,5-dihydroxy-2-hexanone, it is one of the main ]s of ].<ref>Peter Arlien-Søborg. ''Solvent Neurotoxicity''. CRC Press, 1992. {{ISBN|0-8493-6234-2}}. {{Webarchive|url=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 |date=2021-02-21 }}</ref>

2,5-Dimethylfuran has been identified as one of the components of ] ] with low ciliary toxicity (ability to adversely affect the ] in the ] that are responsible for removing foreign particles).<ref>Donald Shopland. ''Cigars: Health Effects and Trends''. DIANE Publishing, 1998. {{Webarchive|url=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 |date=2020-07-24 }}</ref> Its blood concentration can be used as a ] for ].<ref>{{cite journal | doi = 10.1007/BF00381629 | pmid = 8919847 | title = Using the blood concentration of 2,5-dimethylfuran as a marker for smoking | year = 1996 | last1 = Ashley | first1 = D. L. | last2 = Bonin | first2 = M. A. | last3 = Hamar | first3 = B. | last4 = McGeehin | first4 = M. | journal = International Archives of Occupational and Environmental Health | volume = 68 | issue = 3 | pages = 183–7 | bibcode = 1996IAOEH..68..183A | s2cid = 22233967 | url = https://zenodo.org/record/1232436 | access-date = 2020-09-12 | archive-date = 2021-02-21 | archive-url = https://web.archive.org/web/20210221202120/https://zenodo.org/record/1232436 | url-status = live }}</ref>

Comparison of Safety Data Sheets shows that human handling of 2,5-dimethylfuran<ref>{{cite web |url=http://www.fishersci.com/ecomm/servlet/msdsproxy?productName=AC176031000&productDescription=dimethylfuran--acros-organics&catNo=AC176031000&vendorId=VN00032119&storeId=10652 |title=Safety Data Sheet: 2,5-Dimethylfuran |website=Thermo Fisher Scientific |access-date=2014-03-07 |archive-date=2014-03-07 |archive-url=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 |url-status=dead }}</ref><ref>{{cite web |url=http://www.chemicalbook.com/ProductMSDSDetailCB2854009_EN.htm |title=2,5-Dimethylfuran(625-86-5) |website=Chemical Book |access-date=2017-07-21 |archive-date=2017-05-04 |archive-url=https://web.archive.org/web/20170504000607/http://www.chemicalbook.com/ProductMSDSDetailCB2854009_EN.htm |url-status=live }}</ref><ref>{{cite web
|url=http://www.t3db.ca/system/msds/attachments/000/001/956/original/T3D3982.pdf?1414204247
|title=Material Safety Data Sheet 2,5-Dimethylfuran
|date=6 January 2012
|url-status=live
|archive-url=https://web.archive.org/web/20220804123757/http://www.t3db.ca/system/msds/attachments/000/001/956/original/T3D3982.pdf?1414204247
|archive-date=4 August 2022}}</ref> is approximately as hazardous as handling gasoline.<ref>{{cite web|url=http://www.equivashellmsds.com/getsinglemsds.asp?ID=202020 |title=Equiva Services - MSDS |url-status=dead |archiveurl=https://web.archive.org/web/20110710195308/http://www.equivashellmsds.com/getsinglemsds.asp?ID=202020 |archivedate=2011-07-10 }}</ref><ref>{{cite web |url=http://hazard.com/msds/f2/bxw/bxwzb.html |title=hazard.com |access-date=2010-12-27 |archive-date=2011-07-11 |archive-url=https://web.archive.org/web/20110711151929/http://hazard.com/msds/f2/bxw/bxwzb.html |url-status=usurped }}</ref><ref>{{cite web |url=http://hazard.com/msds/f2/bhh/bhhfm.html |title=hazard.com |access-date=2010-12-27 |archive-date=2011-07-11 |archive-url=https://web.archive.org/web/20110711151934/http://hazard.com/msds/f2/bhh/bhhfm.html |url-status=usurped }}</ref>

==References==
{{Portal|Energy}}
{{Reflist|2}}

{{DEFAULTSORT:Dimethylfuran, 2, 5-}}
]
]