Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries.[2] Dimethoxyethane is miscible with water.
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| Names | |
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| Preferred IUPAC name
1,2-Dimethoxyethane[1] | |
| Other names
Ethane-1,2-diyl dimethyl ether[1]
DME Glyme Ethylene glycol dimethyl ether Monoglyme Dimethyl glycol Dimethyl cellosolve | |
| Identifiers | |
3D model (JSmol)
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| Abbreviations | DME |
| 1209237 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.451 |
| EC Number |
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| 1801 | |
PubChem CID
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| RTECS number |
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C4H10O2 | |
| Molar mass | 90.122 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.8683 g/cm3 |
| Melting point | −58 °C (−72 °F; 215 K) |
| Boiling point | 85 °C (185 °F; 358 K) |
| miscible | |
| Hazards | |
| GHS labelling: | |
  
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| Danger | |
| H225, H332, H360FD | |
| P201, P202, P210, P233, P240, P241, P242, P243, P261, P271, P280, P281, P303+P361+P353, P304+P312, P304+P340, P308+P313, P312, P370+P378, P403+P235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | −2 °C (28 °F; 271 K) |
| Related compounds | |
Related Ethers
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Dimethoxymethane |
Related compounds
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Ethylene glycol 1,4-Dioxane Diethylene glycol dimethyl ether |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
editMonoglyme is produced industrially by the reaction of dimethylether with ethylene oxide:[3][4]
- CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3
Applications as solvent and ligand
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Together with a high-permittivity solvent (e.g. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries. In the laboratory, DME is used as a coordinating solvent.
Dimethoxyethane is often used as a higher-boiling-point alternative to diethyl ether and tetrahydrofuran. Dimethoxyethane acts as a bidentate ligand for some metal cations. It is therefore often used in organometallic chemistry. Grignard reactions and hydride reductions are typical application. It is also suitable for palladium-catalyzed reactions including Suzuki reactions and Stille couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.
Sodium naphthalide dissolved in dimethoxyethane is used as a PTFE 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.[6]
References
edit- ^ a b Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 704. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
- ^ D. Berndt, D. Spahrbier, "Batteries" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
- ^ Siegfried Rebsdat; Dieter Mayer (2000). "Ethylene Glycol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 3-527-30673-0.
- ^ Dimethoxyethane
- ^ Arteaga-Müller, Rocío; Tsurugi, Hayato; Saito, Teruhiko; Yanagawa, Masao; Oda, Seiji; Mashima, Kazushi (2009). "New Tantalum Ligand-Free Catalyst System for Highly Selective Trimerization of Ethylene Affording 1-Hexene: New Evidence of a Metallacycle Mechanism". Journal of the American Chemical Society. 131 (15): 5370–5371. doi:10.1021/ja8100837. PMID 20560633.
- ^ "Tetra-Etch FAQ". Weiser Industries USA Inc. Retrieved 29 March 2023.