Dimethoxyethane

Dimethoxyethane
Skeletal formula of dimethoxyethane
Ball-and-stick model of the dimethoxyethane molecule
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
RTECS number KI1451000
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
Flammable (F)
Toxic (T)
Repr. Cat. 2
R-phrases (outdated) R60, R61, R11, R19, R20
S-phrases (outdated) S53, S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
2
2
0
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).
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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

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
2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2↑
CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl

Applications as solvent and ligand

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

  1. 1 2 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.
  2. ↑ D. Berndt, D. Spahrbier, "Batteries" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
  3. ↑ Dimethoxyethane
  4. ↑ Siegfried Rebsdat and Dieter Mayer (2000). "Ethylene Glycol". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_101.
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