Suvarna Garge (Editor)

Dimethoxyethane

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Boiling point
  
85 °C

Density
  
868 kg/m³

Melting point
  
-58 °C

Formula
  
C4H10O2

Molar mass
  
90.12 g/mol

Appearance
  
Colorless liquid

Dimethoxyethane httpsuploadwikimediaorgwikipediacommonsthu

Related compounds
  
Ethylene glycol1,4-DioxaneDiethylene glycol dimethyl ether

Dimethoxyethane meaning


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. Dimethoxyethane is miscible with water.

Contents

Dimethoxyethane FileDimethoxyethane chemical structurepng Wikimedia Commons

Production

Monoglyme may be manufactured by a number of methods:

Dimethoxyethane Glentham Life Sciences GK7433 Ethylene glycol dimethyl ether 1

  • 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
    Dimethoxyethane File12dimethoxyethane 200svg Wikimedia Commons

  • via the alkylation of 2-methoxyethanol with dimethyl sulfate
  • by the cleavage of ethylene oxide in presence of dimethyl ether. This reaction is catalyzed by Lewis acids (e.g. boron trifluoride or its complex with dimethyl ether). This route is not particularly selective and produces diglyme, triglyme, tetraglyme, and other glymes as a by-products. The reaction mixture is separated by distillation:

    • Applications as solvent and ligand

    Dimethoxyethane 11Dimethoxyethane C4H10O2 ChemSpider

    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 File12Dimethoxyethanesvg Wikimedia Commons

    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.

    Dimethoxyethane dimethoxyethane C4H10O2 ChemSpider

    Dimethoxyethane 12Dimethoxyethane CAS 110714 SCBT

    References

    Dimethoxyethane Wikipedia
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