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{{Short description|The simplest ether}}
{{Distinguish|dimethoxyethane}}
{{Chembox
{{Chembox
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 410990799
|verifiedrevid = 438473541
| ImageFileL1 = Dimethyl ether Structural Formulae.svg
|ImageFileL1 = Dimethyl ether Structural Formulae.svg
| ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageNameL1 = Skeletal formula of dimethyl ether with all implicit hydrogens shown
| ImageSizeL1 = 121
|ImageFileR1 = Dimethyl-ether-3D-balls.png
| ImageNameL1 = Skeletal formula of dimethyl ether with all implicit hydrogens shown
|ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageFileR1 = Dimethyl-ether-3D-balls.png
|ImageNameR1 = Ball and stick model of dimethyl ether
| ImageFileR1_Ref = {{chemboximage|correct|??}}
|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>
| ImageSizeR1 = 121
|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
| ImageNameR1 = Ball and stick model of dimethyl ether
|data page pagename = none
| SystematicName = Methoxymethane<ref>{{Cite web|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8254&loc=ec_rcs|title = dimethyl ether - PubChem Public Chemical Database|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>
|Section1={{Chembox Identifiers
| OtherNames = Demeon<br />
|Abbreviations = DME
Dimethyl oxide<br />
|CASNo = 115-10-6
Dymel A<br />
|CASNo_Ref = {{cascite|correct|CAS}}
Methyl ether<br />
|PubChem = 8254
Wood ether
|ChemSpiderID = 7956
| Section1 = {{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| Abbreviations = DME
|UNII = AM13FS69BX
| CASNo = 115-10-6
| CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|EINECS = 204-065-8
| PubChem = 8254
|UNNumber = 1033
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
|KEGG = C11144
| ChemSpiderID = 7956
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|KEGG_Ref = {{keggcite|correct|kegg}}
|MeSHName = Dimethyl+ether
| UNII = AM13FS69BX
| UNII_Ref = {{fdacite|correct|FDA}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 28887
| EINECS = 204-065-8
|ChEMBL = 119178
| UNNumber = 1033
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| KEGG = C11144
|RTECS = PM4780000
| KEGG_Ref = {{keggcite|correct|kegg}}
|Beilstein = 1730743
| MeSHName = Dimethyl+ether
| ChEBI = 28887
|SMILES = COC
|StdInChI = 1S/C2H6O/c1-3-2/h1-2H3
| ChEMBL = 119178
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|InChI = 1/C2H6O/c1-3-2/h1-2H3
| RTECS = PM4780000
|StdInChIKey = LCGLNKUTAGEVQW-UHFFFAOYSA-N
| Beilstein = 1730743
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| SMILES = COC
|InChIKey = LCGLNKUTAGEVQW-UHFFFAOYAU
| 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
|Section2={{Chembox Properties
| C = 2
|C=2 | H=6 | O=1
|Appearance = Colorless gas
| H = 6
|Odor = Ethereal<ref name=GESTIS/>
| O = 1
|Density = 2.1146 kg&nbsp;m<sup>−3</sup> (gas, 0&nbsp;°C, 1013&nbsp;mbar)<ref name=GESTIS>{{GESTIS|ZVG= 25460}}</ref><br />0.735 g/mL (liquid, −25&nbsp;°C)<ref name=GESTIS/>
| ExactMass = 46.041864814 g mol<sup>-1</sup>
|MeltingPtK = 132
| Appearance = Colourless gas
|BoilingPtK = 249
| Odor = Typical
|Solubility = 71&nbsp;g/L (at {{cvt|20|C}})
| Density = 1.97 mg cm<sup>-3</sup>
|LogP = 0.022
| MeltingPtK = 132
|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>
| BoilingPtK = 249
|Dipole = 1.30 D
| Solubility = 71 g dm<sup>-3</sup> (at 20 °C)
|MagSus = {{val|-26.3|e=-6}}&nbsp;cm<sup>3</sup> mol<sup>−1</sup>
| LogP = 0.022
| VaporPressure = >100 kPa
| Dipole = 1.30 D
}}
}}
| Section4 = {{Chembox Thermochemistry
|Section3={{Chembox Thermochemistry
| DeltaHf = -184.1 kJ mol<sup>-1</sup>
|DeltaHf = −184.1 kJ mol<sup>−1</sup>
| DeltaHc = -1.4604 MJ mol<sup>-1</sup>
|DeltaHc = −1460.4 kJ mol<sup>−1</sup>
| HeatCapacity = 65.57 J K<sup>-1</sup> mol<sup>-1</sup>
|HeatCapacity = 65.57 J K<sup>−1</sup> mol<sup>−1</sup>
}}
}}
| Section5 = {{Chembox Hazards
|Section4={{Chembox Hazards
| ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=GB&language=en&productNumber=295299&brand=ALDRICH&PageToGoToURL=https%3A%2F%2Frp.liu233w.com%3A443%2Fhttp%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2F295299%3Flang%3Den ≥99% Sigma-Aldrich]
| ExternalMSDS = [http://msds.chem.ox.ac.uk/DI/dimethyl_ether.html Oxford MSDS]
|GHS_ref = <ref>GHS: {{GESTIS|ZVG=25460}}</ref>
| GHSPictograms = {{GHS flame}}
|GHSPictograms = {{GHS flame}} {{GHS gas cylinder}}
| GHSSignalWord = Danger
|GHSSignalWord = Danger
| HPhrases = {{H-phrases|220}}
| PPhrases = {{P-phrases|210|410+403}}
|HPhrases = {{H-phrases|H220|H280}}
|PPhrases = {{P-phrases|P210|P377|P381|P403}}
| EUIndex = 603-019-00-8
|NFPA-F = 4
| EUClass = {{Hazchem F+}}
|NFPA-H = 2
| RPhrases = {{R12}}
|NFPA-R = 1
| SPhrases = {{S2}}, {{S9}}, {{S16}}, {{S33}}
|ExploLimits = 27&nbsp;%
| NFPA-F = 4
| NFPA-H = 1
|FlashPtC = −41
|AutoignitionPtC = 350
| NFPA-R = 1
| ExploLimits = 27%
| FlashPt = -41 °C
| Autoignition = 350 °C
}}
}}
| Section8 = {{Chembox Related
|Section5={{Chembox Related
| Function = [[ether]]s
|OtherFunction_label = [[ether]]s
| OtherFunctn = [[Diethyl ether]]<br />
|OtherFunction = [[Diethyl ether]]<br />
[[Polyethylene glycol]]
[[Polyethylene glycol]]
| OtherCpds = [[Ethanol]]<br />
|OtherCompounds = [[Ethanol]]<br />
[[Methanol]]
[[Methanol]]
}}
}}
}}
}}


'''Dimethyl ether''' (DME) is the [[organic compound]] with the formula CH<sub>3</sub>OCH<sub>3</sub>. The simplest [[ether]], it is a colourless gas that is a useful precursor to other organic compounds and an aerosol propellant. When combusted, DME produces minimal NOx and CO, though HC and soot formation is significant. DME can act as a clean fuel when burned in engines properly optimized for DME.
'''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==
==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>
Today DME is primarily produced by converting hydrocarbons sourced from [[natural gas]] or [[coal]] via gasification to synthesis gas ([[syngas]]). Synthesis gas is then converted into [[methanol]] in the presence of catalyst (usually copper-based), with subsequent methanol dehydration in the presence of a different catalyst (for example, [[silica-alumina]]) resulting in the production of DME. As described this is a two-step (indirect synthesis) process that starts with methanol synthesis and ends with DME synthesis (methanol dehydration).<ref name=ChemSystems>[http://www.chemsystems.com/reports/search/docs/abstracts/0708S3_abs.pdf Dimethyl Ether Technology and Markets 07/08-S3 Report, ChemSystems, December 2008.]</ref> The same process can be conducted using organic waste or biomass. Approximately 50,000 tons were produced in 1985 in Western Europe using the methanol dehydration process.<ref name=Ullmann>Manfred Müller, Ute Hübsch, “Dimethyl Ether” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.</ref>
:{{chem2|2 CH3OH -> (CH3)2O + H2O}}
Alternatively, DME can be produced through direct synthesis, using a dual catalyst system that permits both methanol synthesis and dehydration in the same process unit, with no methanol isolation and purification, a procedure that by eliminating the intermediate methanol synthesis stage, the licensors claim promises efficiency advantages and cost benefits.<ref name=ChemSystems/><ref>P.S. Sai Prasad et al., Fuel Processing Technology, 2008, 89, 1281.</ref>
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>
Both the one-step and two-step processes above are commercially available. Currently, there is more widespread application of the two-step process since it is relatively simple and start-up costs are relatively low. It is worth mentioning that there is a developing one-step liquid-phase process.<ref name=ChemSystems/><ref>[http://www.airproducts.com/Technology/product_offering.asp?reg=GBL&intProductTypeCategoryId=95&intRegionalMarketSegment=0 Air Products Technology Offerings]</ref>


==Applications==
==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]]:
The largest use of DME is currently (2010) as substitute for [[propane]] in [[LPG]] used as fuel in household and industry.<ref>[http://aboutdme.org/aboutdme/files/ccLibraryFiles/Filename/000000001519/IDA_Fact_Sheet_1_LPG_DME_Blends.pdf IDA Fact Sheet DME/LPG Blends 2010 v1]</ref> The largest use of DME for this purpose is in China. DME has two other primary applications: as a propellant in [[aerosol spray|aerosol canisters]], and as a precursor to [[dimethyl sulfate]].<ref name=Ullmann/><ref>[http://www.demeon.com/ demeon.com, Akzo Nobel DME]</ref> As an aerosol propellant, DME is useful as a somewhat polar solvent. It can also be used as a refrigerant.
:{{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===
===Feedstock===
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>
Several thousand tons of DME are consumed annually for the production of the methylating agent, [[dimethyl sulfate]], which entails its reaction with [[sulfur trioxide]]:
: CH<sub>3</sub>OCH<sub>3</sub> + SO<sub>3</sub> → (CH<sub>3</sub>O)<sub>2</sub>SO<sub>2</sub>


===Niche applications===
DME can also be converted into [[acetic acid]] using [[carbonylation]] technology related to the [[Monsanto acetic acid process]]:<ref name=Ullmann/>
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]]).
: (CH<sub>3</sub>)<sub>2</sub>O + 2 CO + H<sub>2</sub>O → 2 CH<sub>3</sub>CO<sub>2</sub>H


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>
===Laboratory reagent and solvent===

DME is a low-temperature solvent and extraction agent, applicable to specialised laboratory procedures. Its usefulness is limited by its low [[boiling point]] (&minus;23 °C), but the same property facilitates its removal from reaction mixtures. DME 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>
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===
===Fuel===
[[File:Chemrec 5 - small.JPG|thumb|left|Installation of BioDME synthesis towers at Chemrec's pilot facility]]
[[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=live}}</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}}</ref>
DME is a promising fuel in [[diesel engines]],<ref>[http://www.nykomb.se/index.php?s=Chemicals nycomb.se, Nycomb Chemicals company]</ref> [[petrol engine]]s (30% DME / 70% LPG), and [[gas turbines]] owing to its high [[cetane number]], which is 55, compared to diesel's, which is 40–53.<ref>http://www.topsoe.com/site.nsf/all/BBNN-5PNJ3F?OpenDocument topsoe.com</ref> Only moderate modification are needed to convert a diesel engine to burn DME. The simplicity of this short carbon chain compound leads during combustion to very low emissions of particulate matter, NO<sub>x</sub>, CO. For these reasons as well as being sulfur-free, DME meets even the most stringent emission regulations in Europe (EURO5), U.S. (U.S. 2010), and Japan (2009 Japan).<ref>http://www.japantransport.com/conferences/2006/03/dme_detailed_information.pdf, ''Conference on the Development and Promotion of Environmentally Friendly Heavy Duty Vehicles such as DME Trucks'', Washington DC, March 17, '''2006'''</ref> [[Mobil]] is using DME in their [[Gas to liquids|methanol to gasoline]] process.


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 during combustion to very low emissions of particulate matter. 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>
DME is being developed as a synthetic [[second generation biofuel]] (BioDME), which can be manufactured from [[lignocellulosic biomass]].<ref>http://www.biodme.eu/</ref> Currently the EU is considering BioDME in its potential biofuel mix in 2030;<ref>[http://ec.europa.eu/research/energy/pdf/draft_vision_report_en.pdf Biofuels in the European Union, 2006]</ref> the [[Volvo]] Group is the coordinator for the [[European Community]] [[Seventh Framework Programme]] project BioDME<ref>http://www.volvo.com/group/global/en-gb/newsmedia/pressreleases/NewsItemPage.htm?channelId=2184&ItemID=47984&sl=en-gb</ref><ref>http://www.volvo.com/group/global/en-gb/volvo+group/ourvalues/environment/renewable_fuels/biodme/biodme.htm</ref> where [[Chemrec|Chemrec's]] BioDME pilot plant based on [[black liquor]] [[gasification]] is nearing completion 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]</ref>


At the [[Shell Eco-marathon|European Shell Eco Marathon]], an unofficial World Championship for mileage, vehicle running on 100&nbsp;% dimethyl ether drove 589&nbsp;km/L (169.8&nbsp;cm<sup>3</sup>/100&nbsp;km), fuel equivalent to gasoline with a 50&nbsp;cm<sup>3</sup> displacement 2-stroke engine. As well as winning they beat the old standing record of 306&nbsp;km/liter (326.8&nbsp;cm<sup>3</sup>/100&nbsp;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>
The image below illustrates some of processes from various raw materials to DME.
[[Image:DME Process diagram.jpg|none|center|600px]]


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.
In 2009 a team of university students from Denmark won the Urban Concept/Internal Combustion class at the European Shell Eco Marathon (The Shell Eco Marathon is an unofficial World Championship for mileage) with a vehicle running on 100% DME. The vehicle drove 589&nbsp;km/liter, fuel equivalent to gasoline with a 50 ccm 2-stroke engine operating by the Diesel principle. As well as winning they beat the old standing record of 306&nbsp;km/liter, set by the same team in 2007 <ref>[http://www.ecocar.mek.dtu.dk/Achievements.aspx The Danish Ecocar Team - List of achievements]</ref>


=== Refrigerant ===
=== Refrigerant ===
DME is also gaining popularity as a [[refrigerant]]<ref name="mecanica-dme">http://www.mecanica.pub.ro/frigo-eco/R404A_DME.pdf 101110</ref> with [[ASHRAE]] refrigerant designation R-E170. DME is also used in refrigerant blends with e.g. [[butane]] and [[propene]].<ref name ="ASHRAE refrigerants">http://www.ashrae.org/technology/page/1933#et ASHRAE list of refrigerants</ref>
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>

===Treating warts===
A mixture of DME and [[propane]] is used in an over-the-counter device to treat [[warts]], by 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}}</ref><ref>http://www.fda.gov/cdrh/pdf3/K030838.pdf</ref>


==Safety==
==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. [[BASF]] Explosion Disaster on July 28, 1948 in [[Ludwigshafen]] was caused by this compound—200 people died, 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>
Unlike other alkyl ethers, DME resists [[autoxidation]]. DME is also relatively non-toxic, although it is highly flammable.

==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 ==
== References ==
{{Reflist}}
<references/>


==External links ==
== External links ==
* [http://www.aboutdme.org/ The International DME Association]
* [http://www.aboutdme.org/ The International DME Association] {{Webarchive|url=https://web.archive.org/web/20101126124645/http://aboutdme.org/ |date=2010-11-26 }}
* [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}}


{{DEFAULTSORT:Dimethyl Ether}}
[[Category:Aerosol propellants]]
[[Category:Aerosol propellants]]
[[Category:Ethers]]
[[Category:Dialkyl ethers]]
[[Category:Fuels]]
[[Category:Fuels]]
[[Category:Synthetic fuels]]

[[Category:Symmetrical ethers]]
[[cs:Dimethylether]]
[[Category:Organic compounds with 2 carbon atoms]]
[[da:Dimetylæter]]
[[Category:Substances discovered in the 19th century]]
[[de:Dimethylether]]
[[el:Διμεθυλαιθέρας]]
[[es:Éter dimetílico]]
[[fr:Méthoxyméthane]]
[[ko:다이메틸 에테르]]
[[it:Etere dimetilico]]
[[lv:Dimetilēteris]]
[[hu:Dimetil-éter]]
[[mk:Диметил етер]]
[[nl:Dimethylether]]
[[ja:ジメチルエーテル]]
[[pl:Eter dimetylowy]]
[[pt:Dimetil éter]]
[[ru:Диметиловый эфир]]
[[fi:Dimetyylieetteri]]
[[sv:Dimetyleter]]
[[zh:二甲醚]]
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