Dimethoxyethane

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Dimethoxyethane
Skeletal formula of dimethoxyethane
Ball-and-stick model of the dimethoxyethane molecule
Names
IUPAC name
1,2-Dimethoxyethane
Other names
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R-phrases (outdated) R60, R61, R11, R19, R20
S-phrases (outdated) S53, S45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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored 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).
N verify (what is YesYN ?)
Infobox references

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries.[1] Dimethoxyethane is miscible with water.


Production[edit]

Monoglyme may be manufactured by a number of methods:[2]

2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2
CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl
CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

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]

  1. ^ D. Berndt, D. Spahrbier, "Batteries" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
  2. ^ Dimethoxyethane

External links[edit]