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| Names | |
|---|---|
| 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) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.451  |
PubChem CID | |
| RTECS number |
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| UNII | |
CompTox Dashboard (EPA) | |
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SMILES
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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 | |
EU classification (DSD) (outdated) | Flammable (F) Toxic (T) Repr. Cat. 2 |
| R-phrases (outdated) | R60, R61, R11, R19, R20 |
| S-phrases (outdated) | S53, S45 |
| NFPA 704 (fire diamond) | |
| Flash point | −2 °C (28 °F; 271 K) |
| Related compounds | |
Related Ethers | Dimethoxymethane |
Related compounds | 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). | |
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.
Production
Monoglyme 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 alternative to diethyl ether and THF. 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.
References
- ^ 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 and Dieter Mayer (2000). "Ethylene Glycol". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101. ISBN 3527306730.
- ^ 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.