Dimethoxyethane
| 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)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.451 |
PubChem CID
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| RTECS number | KI1451000 |
| |
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| Properties | |
| C4H10O2 | |
| Molar mass | 90.12 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EU classification (DSD) (outdated)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| R-phrases (outdated) | R60, R61, R11, R19, R20 |
| S-phrases (outdated) | S53, S45 |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 | |
| 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). | |
| Infobox references | |
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[edit]
Monoglyme can in principle be produced by a number of methods.[3] In practice it is produced industrially by the reaction of dimethylether with ethylene oxide.[4] Other methods include:
- CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3
- via the Williamson ether synthesis — reacting the sodium salt of 2-methoxyethanol (previously prepared by reaction with sodium) with chloromethane:
- 2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2↑
- CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl
- via the alkylation of 2-methoxyethanol with dimethyl sulfate
Applications as solvent and ligand[edit]
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 forms chelate complexes with cations and acts as a bidentate ligand. It is therefore often used in organometallic chemistry like Grignard reactions, hydride reductions, and palladium-catalyzed reactions like Suzuki reactions and Stille couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.
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
- ^ Dimethoxyethane
- ^ Siegfried Rebsdat and Dieter Mayer (2000). "Ethylene Glycol". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101.