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1,2-dimethoxyethane

Product name 1,2-dimethoxyethane
Synonyms ethylene glycol dimethyl ether
glyme
monoglyme
DME
dimethyl glycol
dimethyl cellosolve
GOST no data
CAS 110-71-4

1,2-Dimethoxyethane (DME) is a clear, colorless, volatile, flammable liquid. It is a parent compound in glymes family. Glymes are ethylene glycol and its oligomers dimethyl ethers CH3O(CH2CH2O)nCH3, where n=1,2,3 and so on. DME is fully miscible with water, methanol, ethanol, diethyl ether, acetone, tetrahydrofuran (THF), benzene, toluene and many others. Soluble in aliphatic hydrocarbons. Dimethoxyethane forms azeotropes with water (boiling point 78.5°C, 10% wt of water), ethanol (77.3°C and 50% wt), chloroform (85.7°C and 22% wt), n-hexane (69.7°C and 79% wt).

DME exhibits the most typical chemical properties ethers. It is stable both in acidic and alkali media, but like other ethers it can be oxidized on air to form dangerous explosive peroxides. DME peroxides are higher boiling and are contact explosives when dry. It should never be distilled to dryness, as the risk of explosion increases dramatically.

Dimethoxyethane is an excellent inert aprotic polar solvent, suitable media for a number of chemical reactions. It forms chelate complexes with metal cations and acts as a bidentate neutral ligand.

DME possess a low toxicity relative to its corresponding glycol mono-ether (methyl cellosolve).

Production.

Dimethoxyethane in commercial quantities can be produced by a variety of methods:

  • via the reaction of methyl cellosolve sodium salt with methyl chloride (Williamson synthesis). Metal alkoxide is prepared previously by interaction of methyl cellosolve with molten sodium at the temperature above 98°C. This reaction is accompanied with hydrogen formation:

    2CH3OCH2CH2OH + 2Na → 2CH3OCH2CH2ONa + H2

    CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl


  • by methylation of methyl cellosolve with methyl sulfate;
  • by the cleavage of ethylene oxide in presence of dimethyl ether. Process is catalyzed with Lewis acids (boron trifluoride BF3 or its dimethyletherate). This route is not particularly selective and produces di- tri, tetra- and other glymes as a by-products. The reaction mixture is separated by complex distillation:

    CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

  • By the reaction of ethylene glycol with methanol in the presence of a polyperfluorosulfonic acid resin catalyst at high temperature and pressure;

    Uses.

  • as a higher boiling alternative to diethyl ether and tetrahydrofuran as an aprotic neutral polar solvent for chemical reactions. It is widely used in organometallic chemistry as a media for Grignard, Suzuki, Heck and other reactions. It is a good solvent for nucleophilic substitutions, Simmons-Smith reaction (addition of carbene to double bond);
  • as a solvent for oligo- and polysaccharides;
  • as a low-viscosity component of the solvent for electrolytes of lithium batteries;
  • for etching of PTFE and other fluoropolymers with alkali metal dispersions;
  • as a solvent for polysilicones;
  • as a reacrion media in pharmaceutical syntheses;
  • as an entrainer;

  • Manufacturer(s) no data
    Chemical structure of 1,2-dimethoxyethane

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