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{{distinguish|dimethoxymethane|dimethyl ether}} |
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{{redirect|Glyme|the river in Oxfordshire, England|River Glyme}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 401996223 |
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|Watchedfields = changed |
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| Name = Dimethoxyethane |
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|verifiedrevid = 441023090 |
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| ImageFile = 1,2-Dimethoxyethane.svg |
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|Name = Dimethoxyethane |
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<!-- | ImageSize = 200px --> |
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| ImageName = Dimethoxyethane |
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|ImageFile = 1,2-Dimethoxyethane.svg |
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|ImageAlt = Skeletal formula of dimethoxyethane |
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| IUPACName = 1,2-Dimethoxyethane |
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|ImageFile1 = Dimethoxyethane 3D ball.png |
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| OtherNames = DME, glyme, monoglyme,<br />dimethyl glycol,<br />ethylene glycol dimethyl ether,<br />dimethyl cellosolve |
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|ImageAlt1 = Ball-and-stick model of the dimethoxyethane molecule |
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| Section1 = {{Chembox Identifiers |
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|PIN = 1,2-Dimethoxyethane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 704 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4}}</ref> |
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| SMILES = CC(OC)OC |
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|OtherNames = Ethane-1,2-diyl dimethyl ether<ref name=iupac2013/><br />DME<br />Glyme<br />Ethylene glycol dimethyl ether<br />Monoglyme<br />Dimethyl glycol<br />Dimethyl cellosolve |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 13854808 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| InChI = 1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 |
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|CASNo = 110-71-4 |
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| InChIKey = SPEUIVXLLWOEMJ-UHFFFAOYAV |
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|Abbreviations = DME |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|Beilstein = 1209237 |
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| StdInChI = 1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID = 13854808 |
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| StdInChIKey = SPEUIVXLLWOEMJ-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| CASNo = 110-71-4 |
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|ChEBI = 42263 |
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|EC_number = 203-794-9 |
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| RTECS = KI1451000 |
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|Gmelin = 1801 |
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}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Section2 = {{Chembox Properties |
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|UNII = GXS24JF5IW |
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| Formula = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub> |
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|RTECS = KI1451000 |
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| MolarMass = 90.12 g/mol |
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|PubChem = 8071 |
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| Appearance = colorless liquid |
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|SMILES = COCCOC |
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| Density = 0.8683 g/cm<sup>3</sup>, liquid |
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|InChI = 1/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 |
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| Solubility = miscible |
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|InChIKey = SPEUIVXLLWOEMJ-UHFFFAOYAV |
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| MeltingPt = -58 °C |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| BoilingPt = 85 °C |
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|StdInChI = 1S/C4H10O2/c1-4(5-2)6-3/h4H,1-3H3 |
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| Viscosity = |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|StdInChIKey = SPEUIVXLLWOEMJ-UHFFFAOYSA-N |
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| Section3 = {{Chembox Structure |
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}} |
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| Dipole = |
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|Section2={{Chembox Properties |
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}} |
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|C=4 | H=10 | O=2 |
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| Section7 = {{Chembox Hazards |
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|Appearance = Colorless liquid |
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| ExternalMSDS = |
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|Density = 0.8683 g/cm<sup>3</sup> |
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| NFPA-H = 2 |
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|Solubility = miscible |
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| NFPA-F = 3 |
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|MeltingPtC = -58 |
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| NFPA-R = 2 |
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|BoilingPtC = 85 |
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| EUClass = Flammable ('''F''')<br />Toxic ('''T''')<br />Repr. Cat. 2 |
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}} |
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| RPhrases = {{R60}}, {{R61}}, {{R11}}, {{R19}}, {{R20}} |
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|Section7={{Chembox Hazards |
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| SPhrases = {{S53}}, {{S45}} |
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|NFPA-H = 2 |
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| FlashPt = −2 °C |
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|NFPA-F = 2 |
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}} |
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|NFPA-R = 0 |
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| Section8 = {{Chembox Related |
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|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}} |
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| Function = ]s |
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|GHSSignalWord = Danger |
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| OtherFunctn = ] |
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|HPhrases = {{H-phrases|225|332|360FD}} |
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| OtherCpds = ]<br />] |
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|PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|261|271|280|281|303+361+353|304+312|304+340|308+313|312|370+378|403+235|405|501}} |
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}} |
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|FlashPtC = −2 |
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}} |
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|Section8={{Chembox Related |
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|OtherFunction_label = ]s |
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|OtherFunction = ] |
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|OtherCompounds = ]<br />]<br />] |
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}} |
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}} |
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}} |
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'''Dimethoxyethane''', also known as '''glyme''', '''monoglyme''', '''dimethyl glycol''', '''ethylene glycol dimethyl ether''', '''dimethyl cellosolve''', and '''DME''', is a clear, colorless, aprotic, and liquid ] that is used as a ]. Dimethoxyethane is ] with ]. |
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'''Dimethoxyethane''', also known as '''glyme''', '''monoglyme''', '''dimethyl glycol''', '''ethylene glycol dimethyl ether''', '''dimethyl cellosolve''', and '''DME''', is a colorless, ], and liquid ] that is used as a ], especially in batteries.<ref>D. Berndt, D. Spahrbier, "Batteries" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a03_343}}</ref> Dimethoxyethane is ] with ]. |
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==Production== |
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Dimethoxyethane is often used as a higher boiling alternative to ] and ]. Dimethoxyethane forms ] complexes with ] and acts as a bidentate ]. It is therefore often used in ] like ]s, ]s, and ] like ]s and ]. Dimethoxyethane is also a good solvent for ]- and ]. |
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Monoglyme is produced industrially by the reaction of ] with ]:<ref>{{cite encyclopedia|author=Siegfried Rebsdat |author2=Dieter Mayer |chapter=Ethylene Glycol|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|publisher=Wiley-VCH|place=Weinheim|doi=10.1002/14356007.a10_101|isbn=3-527-30673-0}}</ref><ref></ref> |
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:CH<sub>3</sub>OCH<sub>3</sub> + CH<sub>2</sub>CH<sub>2</sub>O → CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub> |
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==Applications as solvent and ligand== |
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The lowest energy form of dimethoxyethane in the gas phase is the gauche, rather than the anti conformer. |
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] NbCl<sub>3</sub>(dimethoxyethane)(3-hexyne).<ref>{{cite journal |doi=10.1021/ja8100837|title=New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism|year=2009|last1=Arteaga-Müller|first1=Rocío|last2=Tsurugi|first2=Hayato|last3=Saito|first3=Teruhiko|last4=Yanagawa|first4=Masao|last5=Oda|first5=Seiji|last6=Mashima|first6=Kazushi|journal=Journal of the American Chemical Society|volume=131|issue=15|pages=5370–5371|pmid=20560633}}</ref>]] |
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Together with a high-] solvent (e.g. ]), dimethoxyethane is used as the low-] component of the solvent for ]s of ]. In the laboratory, DME is used as a coordinating solvent. |
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Dimethoxyethane is often used as a higher-boiling-point alternative to ] and ]. Dimethoxyethane acts as a bidentate ] for some metal cations. It is therefore often used in ]. ]s and ]s are typical application. It is also suitable for ] including ]s and ]s. Dimethoxyethane is also a good solvent for ]- and ]s. |
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==Production== |
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Monoglyme may be manufactured by a number of methods:<ref></ref> |
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* via the ] — reacting the sodium salt of ] (previously prepared by reaction with ]) with ]: |
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:2 CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OH + 2 Na → 2 CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>ONa + H<sub>2</sub>↑ |
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:CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>ONa + CH<sub>3</sub>Cl → CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub> + NaCl |
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* via the ] of 2-methoxyethanol with ] |
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* by the cleavage of ] in presence of ]. This reaction is catalyzed by ] (e.g. ] or its complex with dimethyl ether). This route is not particularly selective and produces diglyme, triglyme, tetraglyme, and other glymes as a by-products. The reaction mixture is separated by ]: |
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::CH<sub>3</sub>OCH<sub>3</sub> + CH<sub>2</sub>CH<sub>2</sub>O → CH<sub>3</sub>OCH<sub>2</sub>CH<sub>2</sub>OCH<sub>3</sub> |
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] dissolved in dimethoxyethane is used as a ] etching solution that removes fluorine atoms from the surface, which get replaced by oxygen, hydrogen, and water. This physically etches the surface as well to prepare the surface for better adhesion.<ref>{{cite web |title=Tetra-Etch FAQ |url=https://weiserindustries.com/tetra-etch-faq |website=Weiser Industries USA Inc. |access-date=29 March 2023}}</ref> |
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==Uses== |
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Together with a high-] chemical (e.g. ]), dimethoxyethane is used as the low-] component of the solvent for ]s of ]. |
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==References== |
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==References== |
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==External links== |
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