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Dimethyl ether
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{{Short description|The simplest ether}} {{Distinguish|dimethoxyethane}} {{Chembox |Watchedfields = changed |verifiedrevid = 438473541 |ImageFileL1 = Dimethyl ether Structural Formulae.svg |ImageFileL1_Ref = {{chemboximage|correct|??}} |ImageNameL1 = Skeletal formula of dimethyl ether with all implicit hydrogens shown |ImageFileR1 = Dimethyl-ether-3D-balls.png |ImageFileR1_Ref = {{chemboximage|correct|??}} |ImageNameR1 = Ball and stick model of dimethyl ether |PIN = Methoxymethane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 703 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4| chapter = CHAPTER P-6. Applications to Specific Classes of Compounds }}</ref> |OtherNames = Dimethyl ether<ref name=iupac2013/><br />R-E170<br />Demeon<br />Dimethyl oxide<br />Dymel A<br />Methyl ether<br /> Methyl oxide<br />Mether<br />Wood ether |data page pagename = none |Section1={{Chembox Identifiers |Abbreviations = DME |CASNo = 115-10-6 |CASNo_Ref = {{cascite|correct|CAS}} |PubChem = 8254 |ChemSpiderID = 7956 |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |UNII = AM13FS69BX |UNII_Ref = {{fdacite|correct|FDA}} |EINECS = 204-065-8 |UNNumber = 1033 |KEGG = C11144 |KEGG_Ref = {{keggcite|correct|kegg}} |MeSHName = Dimethyl+ether |ChEBI_Ref = {{ebicite|correct|EBI}} |ChEBI = 28887 |ChEMBL = 119178 |ChEMBL_Ref = {{ebicite|correct|EBI}} |RTECS = PM4780000 |Beilstein = 1730743 |SMILES = COC |StdInChI = 1S/C2H6O/c1-3-2/h1-2H3 |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |InChI = 1/C2H6O/c1-3-2/h1-2H3 |StdInChIKey = LCGLNKUTAGEVQW-UHFFFAOYSA-N |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |InChIKey = LCGLNKUTAGEVQW-UHFFFAOYAU }} |Section2={{Chembox Properties |C=2 | H=6 | O=1 |Appearance = Colorless gas |Odor = Ethereal<ref name=GESTIS/> |Density = 2.1146 kg m<sup>−3</sup> (gas, 0 °C, 1013 mbar)<ref name=GESTIS>{{GESTIS|ZVG= 25460}}</ref><br />0.735 g/mL (liquid, −25 °C)<ref name=GESTIS/> |MeltingPtK = 132 |BoilingPtK = 249 |Solubility = 71 g/L (at {{cvt|20|C}}) |LogP = 0.022 |VaporPressure = 592.8 kPa<ref>{{Cite web|url = https://encyclopedia.airliquide.com/dimethylether|title = Dimethylether|date = 19 October 2018|access-date = 10 November 2020|archive-date = 6 November 2021|archive-url = https://web.archive.org/web/20211106032850/https://encyclopedia.airliquide.com/dimethylether|url-status = live}}</ref> |Dipole = 1.30 D |MagSus = {{val|-26.3|e=-6}} cm<sup>3</sup> mol<sup>−1</sup> }} |Section3={{Chembox Thermochemistry |DeltaHf = −184.1 kJ mol<sup>−1</sup> |DeltaHc = −1460.4 kJ mol<sup>−1</sup> |HeatCapacity = 65.57 J K<sup>−1</sup> mol<sup>−1</sup> }} |Section4={{Chembox Hazards | ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=GB&language=en&productNumber=295299&brand=ALDRICH&PageToGoToURL=http%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F295299%3Flang%3Den ≥99% Sigma-Aldrich] |GHS_ref = <ref>GHS: {{GESTIS|ZVG=25460}}</ref> |GHSPictograms = {{GHS flame}} |GHSSignalWord = Danger |HPhrases = {{H-phrases|H220}} |PPhrases = {{P-phrases|P210|P377|P381|P403}} |NFPA-F = 4 |NFPA-H = 2 |NFPA-R = 1 |ExploLimits = 27 % |FlashPtC = −41 |AutoignitionPtC = 350 }} |Section5={{Chembox Related |OtherFunction_label = [[ether]]s |OtherFunction = [[Diethyl ether]]<br /> [[Polyethylene glycol]] |OtherCompounds = [[Ethanol]]<br /> [[Methanol]] }} }} '''Dimethyl ether''' ('''DME'''; also known as '''methoxymethane''') is the [[organic compound]] with the formula CH<sub>3</sub>OCH<sub>3</sub>, (sometimes ambiguously simplified to C<sub>2</sub>H<sub>6</sub>O as it is an [[isomer]] of [[ethanol]]). The simplest [[ether]], it is a colorless gas that is a useful precursor to other organic compounds and an aerosol propellant that is currently being demonstrated for use in a variety of fuel applications. Dimethyl ether was first synthesised by [[Jean-Baptiste Dumas]] and [[Eugene Péligot]] in 1835 by distillation of methanol and sulfuric acid.<ref>Ann. chim. phys., 1835, [2] 58, p. 19 </ref> ==Production== Approximately 50,000 tons were produced in 1985 in Western Europe by [[dehydration reaction|dehydration]] of [[methanol]]:<ref name=Ullmann>Manfred Müller, Ute Hübsch, "Dimethyl Ether" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a08_541}}</ref> :{{chem2|2 CH3OH -> (CH3)2O + H2O}} The required methanol is obtained from synthesis gas ([[syngas]]).<ref name=ChemSystems>{{cite web|url=http://www.chemsystems.com/reports/search/docs/abstracts/0708S3_abs.pdf|title=CHEMSYSTEMS.COM|website=www.chemsystems.com|access-date=1 April 2018|archive-url=https://web.archive.org/web/20091122170413/http://www.chemsystems.com/reports/search/docs/abstracts/0708S3_abs.pdf|archive-date=22 November 2009|url-status=dead}}</ref> Other possible improvements call for a dual catalyst system that permits both methanol synthesis and dehydration in the same process unit, with no methanol isolation and purification.<ref name=ChemSystems/><ref>P.S. Sai Prasad et al., Fuel Processing Technology, 2008, 89, 1281.</ref> Both the one-step and two-step processes above are commercially available. The two-step process is relatively simple and start-up costs are relatively low. A one-step liquid-phase process is in development.<ref name=ChemSystems/><ref>{{cite web|url=http://www.airproducts.com/Technology/product_offering.asp?reg=GBL&intProductTypeCategoryId=95&intRegionalMarketSegment=0|title=Air Products Technology Offerings|website=airproducts.com|access-date=1 April 2018|archive-url=https://web.archive.org/web/20071212191702/http://www.airproducts.com/technology/product_offering.asp?reg=GBL&intProductTypeCategoryId=95&intRegionalMarketSegment=0|archive-date=12 December 2007|url-status=dead}}</ref> ===From biomass=== Dimethyl ether is a synthetic [[second generation biofuel]] (BioDME), which can be produced from [[lignocellulosic biomass]].<ref>{{cite web|url=http://www.biodme.eu/|title=BioDME|website=www.biodme.eu|access-date=1 April 2018|archive-date=10 April 2020|archive-url=https://web.archive.org/web/20200410183454/http://www.biodme.eu/|url-status=live}}</ref> The EU is considering BioDME in its potential biofuel mix in 2030;<ref>{{cite web|url=http://ec.europa.eu/research/energy/pdf/draft_vision_report_en.pdf|title=Biofuels in the European Union, 2006|website=europa.eu|access-date=1 April 2018|archive-date=3 December 2019|archive-url=https://web.archive.org/web/20191203221230/http://ec.europa.eu/research/energy/pdf/draft_vision_report_en.pdf|url-status=live}}</ref> It can also be made from [[biogas]] or [[methane]] from animal, food, and agricultural waste,<ref>{{Cite web |url=http://oberonfuels.com/2013/06/07/oberon-fuels-brings-production-units-online-launching-the-first-north-american-fuel-grade-dme-facilities/ |title=Oberon Fuels Brings Production Units Online, Launching the First North American Fuel-grade DME Facilities |date=7 June 2013 |access-date=2018-08-04 |archive-date=2021-05-06 |archive-url=https://web.archive.org/web/20210506070121/https://oberonfuels.com/2013/06/07/oberon-fuels-brings-production-units-online-launching-the-first-north-american-fuel-grade-dme-facilities/ |url-status=live }}</ref><ref>{{Cite web |url=http://siteresources.worldbank.org/EXTGGFR/Resources/AG_utilization_via_mini_GTL.pdf?resourceurlname=AG_utilization_via_mini_GTL.pdf |title=Associated Gas Utilization via mini GTL |access-date=2018-08-04 |archive-date=2018-08-04 |archive-url=https://web.archive.org/web/20180804201342/http://siteresources.worldbank.org/EXTGGFR/Resources/AG_utilization_via_mini_GTL.pdf?resourceurlname=AG_utilization_via_mini_GTL.pdf |url-status=live }}</ref> or even from [[shale gas]] or [[natural gas]].<ref>{{Cite book |doi = 10.1016/S0167-2991(04)80081-8|chapter = Direct Dimethyl Ether (DME) synthesis from natural gas|title = Natural Gas Conversion VII, Proceedings of the 7th Natural Gas Conversion Symposium|volume = 147|pages = 379–384|series = Studies in Surface Science and Catalysis|year = 2004|last1 = Ogawa|first1 = Takashi|last2 = Inoue|first2 = Norio|last3 = Shikada|first3 = Tutomu|last4 = Inokoshi|first4 = Osamu|last5 = Ohno|first5 = Yotaro|isbn = 9780444515995}}</ref> The [[Volvo]] Group is the coordinator for the [[European Community]] [[Seventh Framework Programme]] project BioDME<ref>{{cite web |url=http://www.volvo.com/group/global/en-gb/newsmedia/pressreleases/NewsItemPage.htm?channelId=2184&ItemID=47984&sl=en-gb |title=Home {{pipe}} Volvo Group |access-date=2011-11-04 |url-status=dead |archive-url=https://web.archive.org/web/20090525045327/http://www.volvo.com/group/global/en-gb/newsmedia/pressreleases/NewsItemPage.htm?channelId=2184&ItemID=47984&sl=en-gb |archive-date=2009-05-25 }}</ref><ref>{{cite web|url=http://www.volvo.com/group/global/en-gb/volvo+group/ourvalues/environment/renewable_fuels/biodme/biodme.htm|title=Volvo Group - Driving prosperity through transport solutions|website=www.volvo.com|access-date=1 April 2018|archive-date=6 June 2020|archive-url=https://web.archive.org/web/20200606064458/https://www.volvogroup.com/en-en/home.html|url-status=dead}}</ref> where [[Chemrec]]'s BioDME pilot plant is based on [[black liquor]] [[gasification]] in [[Piteå]], [[Sweden]].<ref>[http://www.chemrec.se/admin/UploadFile.aspx?path=/UserUploadFiles/Pressreleaser%202010/The-first-BioDME-plant-in-the-world-inaugurated_1.pdf Chemrec press release September 9, 2010] {{webarchive|url=https://web.archive.org/web/20170612010101/http://www.chemrec.se/admin/UploadFile.aspx?path=%2FUserUploadFiles%2FPressreleaser+2010%2FThe-first-BioDME-plant-in-the-world-inaugurated_1.pdf |date=June 12, 2017 }}</ref> ==Applications== The largest use of dimethyl ether is as the feedstock for the production of the methylating agent, [[dimethyl sulfate]], which entails its reaction with [[sulfur trioxide]]: :{{chem2|CH3OCH3 + SO3 -> (CH3)2SO4}} Dimethyl ether can also be converted into [[acetic acid]] using [[carbonylation]] technology related to the [[Monsanto acetic acid process]]:<ref name=Ullmann/> :{{chem2|(CH3)2O + 2 CO + H2O -> 2 CH3CO2H}} ===Laboratory reagent and solvent=== Dimethyl ether is a low-temperature solvent and extraction agent, applicable to specialised laboratory procedures. Its usefulness is limited by its low [[boiling point]] ({{convert|-23|C}}), but the same property facilitates its removal from reaction mixtures. Dimethyl ether is the precursor to the useful [[alkylating agent]], [[trimethyloxonium tetrafluoroborate]].<ref>{{OrgSynth | author = T. J. Curphey | collvol = 6 | year = 1988| collvolpages = 1019 | prep = CV6P1019| title = Trimethyloxonium tetrafluoroborate}}</ref> ===Niche applications=== A mixture of dimethyl ether and [[propane]] is used in some over-the-counter "[[freeze spray]]" products to treat [[wart]]s by [[cryosurgery|freezing them]].<ref>{{cite news | url = http://www.pharmacytimes.com/issue/pharmacy/2006/2006-07/2006-07-5674 | date = July 2006 | title = A Pharmacist's Guide to OTC Therapy: OTC Treatments for Warts | access-date = 2009-05-02 | archive-url = https://web.archive.org/web/20100617043246/http://www.pharmacytimes.com/issue/pharmacy/2006/2006-07/2006-07-5674 | archive-date = 2010-06-17 | url-status = dead }}</ref><ref>{{Cite web |url=https://www.fda.gov/cdrh/pdf3/K030838.pdf |title=Archived copy |website=[[Food and Drug Administration]] |access-date=2019-12-16 |archive-date=2009-04-20 |archive-url=https://web.archive.org/web/20090420005111/http://www.fda.gov/cdrh/pdf3/k030838.pdf |url-status=dead }}</ref> In this role, it has supplanted halocarbon compounds ([[Freon]]). Dimethyl ether is also a component of certain high temperature [[MAPP gas|"Map-Pro"]] blowtorch gas blends, supplanting the use of [[methyl acetylene]] and [[propadiene]] mixtures.<ref name="MAP-Plus">{{Cite web |url=http://images.toolbank.com/downloads/cossh/0482.pdf |title=Archived copy |access-date=2016-03-02 |archive-date=2016-12-20 |archive-url=https://web.archive.org/web/20161220132220/http://images.toolbank.com/downloads/cossh/0482.pdf |url-status=dead}}</ref> Dimethyl ether is also used as a propellant in aerosol products. Such products include hair spray, bug spray and some aerosol glue products. ==Research== ===Fuel=== [[File:Chemrec 5 - small.JPG|thumb|left|Installation of BioDME synthesis towers at Chemrec's pilot facility]] A potentially major use of dimethyl ether is as substitute for [[propane]] in [[Liquefied petroleum gas|LPG]] used as fuel in household and industry.<ref>{{cite web|url=http://aboutdme.org/aboutdme/files/ccLibraryFiles/Filename/000000001519/IDA_Fact_Sheet_1_LPG_DME_Blends.pdf|title=IDA Fact Sheet DME/LPG Blends 2010 v1|website=aboutdme.org|access-date=1 April 2018|archive-date=24 July 2011|archive-url=https://web.archive.org/web/20110724214522/http://aboutdme.org/aboutdme/files/ccLibraryFiles/Filename/000000001519/IDA_Fact_Sheet_1_LPG_DME_Blends.pdf|url-status=usurped}}</ref> Dimethyl ether can also be used as a blendstock in propane [[autogas]].<ref>{{Cite journal|url= https://doi.org/10.1016/j.jngse.2012.05.012|title= The Status of DME developments in China and beyond, 2012|journal= Journal of Natural Gas Science and Engineering|date= November 2012|volume= 9|pages= 94–107|doi= 10.1016/j.jngse.2012.05.012|last1= Fleisch|first1= T. H.|last2= Basu|first2= A.|last3= Sills|first3= R. A.|access-date= 2020-11-21|archive-date= 2022-05-04|archive-url= https://web.archive.org/web/20220504141337/https://www.sciencedirect.com/science/article/pii/S1875510012000650?via%3Dihub|url-status= live|url-access= subscription}}</ref> It is also a promising fuel in [[diesel engines]],<ref>[http://www.nykomb.se/index.php?s=Chemicals nycomb.se, Nycomb Chemicals company] {{webarchive|url=https://web.archive.org/web/20080603115705/http://www.nykomb.se/index.php?s=Chemicals |date=2008-06-03 }}</ref> and [[gas turbines]]. For diesel engines, an advantage is the high [[cetane number]] of 55, compared to that of [[diesel fuel]] from petroleum, which is 40–53.<ref>{{cite web |url=http://www.topsoe.com/site.nsf/all/BBNN-5PNJ3F?OpenDocument |title=Haldor Topsoe - Products & Services - Technologies - DME - Applications - DME as Diesel Fuel |access-date=2011-11-04 |url-status=dead |archive-url=https://web.archive.org/web/20071008100421/http://www.topsoe.com/site.nsf/all/BBNN-5PNJ3F?OpenDocument |archive-date=2007-10-08 }} topsoe.com</ref> Only moderate modifications are needed to convert a diesel engine to burn dimethyl ether. The simplicity of this short carbon chain compound leads to very low emissions of particulate matter during combustion. For these reasons as well as being sulfur-free, dimethyl ether meets even the most stringent emission regulations in Europe ([[European emission standards|EURO5]]), U.S. (U.S. 2010), and Japan (2009 Japan).<ref>{{cite web |url=http://www.japantransport.com/conferences/2006/03/dme_detailed_information.pdf |title=Archived copy |access-date=2011-11-04 |url-status=dead |archive-url=https://web.archive.org/web/20090107022359/http://www.japantransport.com/conferences/2006/03/dme_detailed_information.pdf |archive-date=2009-01-07 }}, ''Conference on the Development and Promotion of Environmentally Friendly Heavy Duty Vehicles such as DME Trucks'', Washington DC, March 17, '''2006'''</ref> At the [[Shell Eco-marathon|European Shell Eco Marathon]], an unofficial World Championship for mileage, vehicle running on 100 % dimethyl ether drove 589 km/L (169.8 cm<sup>3</sup>/100 km), fuel equivalent to gasoline with a 50 cm<sup>3</sup> displacement 2-stroke engine. As well as winning they beat the old standing record of 306 km/liter (326.8 cm<sup>3</sup>/100 km), set by the same team in 2007.<ref>{{cite web|url=http://www.ecocar.mek.dtu.dk/Achievements.aspx|title=The Danish Ecocar Team - List of achievements|website=dtu.dk|access-date=1 April 2018|archive-url=https://web.archive.org/web/20091017150928/http://www.ecocar.mek.dtu.dk/Achievements.aspx|archive-date=17 October 2009|url-status=dead}}</ref> To study the dimethyl ether for the combustion process a chemical kinetic mechanism<ref>{{Cite journal|url = https://doi.org/10.1016/j.combustflame.2020.04.016|doi = 10.1016/j.combustflame.2020.04.016|title = A comprehensive kinetic model for dimethyl ether and dimethoxymethane oxidation and NO interaction utilizing experimental laminar flame speed measurements at elevated pressure and temperature|year = 2020|last1 = Shrestha|first1 = Krishna P.|last2 = Eckart|first2 = Sven|last3 = Elbaz|first3 = Ayman M.|last4 = Giri|first4 = Binod R.|last5 = Fritsche|first5 = Chris|last6 = Seidel|first6 = Lars|last7 = Roberts|first7 = William L.|last8 = Krause|first8 = Hartmut|last9 = Mauss|first9 = Fabian|journal = Combustion and Flame|volume = 218|pages = 57–74|hdl = 10754/662921|s2cid = 219772095|hdl-access = free|access-date = 2020-05-18|archive-date = 2022-05-04|archive-url = https://web.archive.org/web/20220504141322/https://www.sciencedirect.com/science/article/pii/S0010218020301607?via%3Dihub|url-status = live}}</ref> is required which can be used for Computational fluid dynamics calculation. === Refrigerant === Dimethyl ether is a [[refrigerant]] with [[ASHRAE]] refrigerant designation R-E170. It is also used in refrigerant blends with e.g. [[ammonia]], [[carbon dioxide]], [[butane]] and [[propene]]. Dimethyl ether was the first refrigerant. In 1876, the French engineer [[Charles Tellier]] bought the ex-Elder-Dempster a 690 tons cargo ship ''Eboe'' and fitted a methyl-ether [[Reefer ship|refrigerating]] plant of his design. The ship was renamed ''Le Frigorifique'' and successfully imported a cargo of refrigerated meat from [[Argentina]]. However the machinery could be improved and in 1877 another refrigerated ship called ''Paraguay'' with a refrigerating plant improved by [[Ferdinand Carré]] was put into service on the South American run.<ref>[https://archive.org/stream/historyoffrozenm00crituoft/historyoffrozenm00crituoft_djvu.txt A history of the frozen meat trade, page 26-28]</ref><ref name ="ASHRAE refrigerants">http://www.ashrae.org/technology/page/1933#et {{Webarchive|url=https://web.archive.org/web/20120103000626/http://www.ashrae.org/technology/page/1933#et |date=2012-01-03}} ASHRAE list of refrigerants</ref> ==Safety== Unlike other alkyl ethers, dimethyl ether resists [[autoxidation]].<ref>''A comparative study on the autoxidation of dimethyl ether (DME) comparison with diethyl ether (DEE) and diisopropyl ether (DIPE)'', Michie Naito, Claire Radcliffe, Yuji Wada, Takashi Hoshino, Xiongmin Liu, Mitsuru Arai, Masamitsu Tamura. Journal of Loss Prevention in the Process Industries, Volume 18, Issues 4–6, July–November 2005, Pages 469–473 [https://doi.org/10.1016/j.jlp.2005.07.001 DOI]</ref> Dimethyl ether is also relatively non-toxic, although it is highly flammable. On July 28, 1948, a [[BASF]] factory in [[Ludwigshafen]] suffered an explosion after 30 tonnes of dimethyl ether leaked from a tank and ignited in the air. 200 people died, and a third of the industrial plant was destroyed.<ref>[https://www.filmothek.bundesarchiv.de/video/583599?topic=doc70ohy4pxya038cw67f7&start=00%3A01%3A01.20&end=00%3A02%3A00.19 Welt im Film 167/1948] {{Webarchive|url=https://web.archive.org/web/20210129152538/https://www.filmothek.bundesarchiv.de/video/583599?topic=doc70ohy4pxya038cw67f7&start=00%3A01%3A01.20&end=00%3A02%3A00.19 |date=2021-01-29 }}. filmothek.bundesarchiv.de</ref> ==Data sheet== ===Routes to produce dimethyl ether=== [[File:DME process diagram.svg|600px]] ===Vapor pressure=== {| class="wikitable" style=text-align:right |+ Experimental vapor pressures of dimethyl ether<ref>{{cite journal|doi=10.1021/je0340046|journal=J. Chem. Eng. Data|url=https://doi.org/10.1021/je0340046|title=Vapor Pressure Measurements of Dimethyl Ether from (233 to 399) K|first1=Jiangtao|last1=Wu|first2=Zhigang|last2=Liu|first3=Jiang|last3=Pan|first4=Xiaoming|last4=Zhao|date=2003-11-25|volume=49|pages=32–34|url-access=subscription|access-date=2022-01-07|archive-date=2022-05-04|archive-url=https://web.archive.org/web/20220504141329/https://pubs.acs.org/doi/10.1021/je0340046|url-status=live}}</ref> |- ! Temperature (K) !! Pressure (kPa) |- | 233.128 || 54.61 |- | 238.126 || 68.49 |- | 243.157 || 85.57 |- | 248.152 || 105.59 |- | 253.152 || 129.42 |- | 258.16{{figure space}} || 157.53 |- | 263.16{{figure space}} || 190.44 |- | 268.161 || 228.48 |- | 273.153 || 272.17 |- | 278.145 || 321.87 |- | 283.16{{figure space}} || 378.66 |- | 288.174 || 443.57 |- | 293.161 || 515.53 |- | 298.172 || 596.21 |- | 303.16{{figure space}} || 687.37 |- | 305.16{{figure space}} || 726.26 |- | 308.158 || 787.07 |- | 313.156 || 897.59 |- | 316.154 || 968.55 |- | 318.158 || 1018.91 |- | 323.148 || 1152.35 |- | 328.149 || 1298.23 |- | 333.157 || 1457.5{{figure space}} |- | 333.159 || 1457.76 |- | 338.154 || 1631.01 |- | 343.147 || 1818.8{{figure space}} |- | 348.147 || 2022.45 |- | 353.146 || 2242.74 |- | 353.158 || 2243.07 |- | 358.145 || 2479.92 |- | 363.148 || 2735.67 |- | 368.158 || 3010.81 |- | 373.154 || 3305.67 |- | 378.15{{figure space}} || 3622.6{{figure space}} |- | 383.143 || 3962.25 |- | 388.155 || 4331.48 |- | 393.158 || 4725.02 |- | 398.157 || 5146.82 |- | 400.378 || 5355.8{{figure space}} |} ==See also== * [[Methanol economy]] == References == {{Reflist}} == External links == * {{usurped|1=[https://web.archive.org/web/20101126124645/http://aboutdme.org/ The International DME Association]}} * [https://cameochemicals.noaa.gov/chemical/585 NOAA site for NFPA 704] * [http://www.xtlinstitute.com/ XTL & DME Institute] {{Molecules detected in outer space}} {{Authority control}} [[Category:Aerosol propellants]] [[Category:Dialkyl ethers]] [[Category:Fuels]] [[Category:Synthetic fuels]] [[Category:Symmetrical ethers]] [[Category:Organic compounds with 2 carbon atoms]] [[Category:Substances discovered in the 19th century]]
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