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diglyme

Product name diglyme
Synonyms diethylene glycol dimethyl ether
2-methoxyethyl ether
bis(2-methoxyethyl) ether
GOST no data
CAS 111-96-6

Diglyme is a clear, colorless liquid with a slight ether-like odor. It is fukky miscible in water, ethanol, methanol, acetone, THF, dimethyl sulfoxide (DMSO), benzene, acetic acid, pyridine, petroleum ether and many other organic solvents. It forms aseotropes with water (bp 99.3°C, 77% wt of water) and phenol (189°C, 62% wt of phenol). Diglyme is a second compound in glymes family, ethylene glycol and its oligomers dimethyl ethers with a chemical formula CH3O(CH2CH2O)nCH3, where n=1,2,3 and so on.

Diglyme exhibits the most typical chemical properties ethers. C-O bond is stable, therefore diglyme possess a low reactivity. It is a very powerful, aprotic, high-boiling solvent, used in many industrial applications. It is able to dissolve a wide range of organic and inorganic compounds, hence it is a suitable solvent for chemical reactions. Diglyme chelate small cations, leaving anions more active.

Diglyme possess a relatively low toxicity.

Production.

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

  • via the reaction of methyl carbitol sodium salt with methyl chloride (Williamson synthesis). Metal alkoxide is synthesized by interaction of methyl carbitol with molten sodium:

    2CH3O(CH2CH2O)2H + 2Na → 2CH3O(CH2CH2O)2Na + H2
    CH3O(CH2CH2O)2Na + CH3Cl → CH3O(CH2CH2O)2CH3 + NaCl


  • by methylation of methyl carbitol 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 mono-, di- tri, tetra- and other glymes as a by-products. The reaction mixture is separated by complex distillation:

    CH3OCH3 + CH2CH2O → CH3O(CH2CH2O)nCH3 (n = 1, 2, 3)

  • By the reaction of diethylene glycol with methanol in the presence of a polyperfluorosulfonic acid resin catalyst at high temperature and pressure (US patent);

    Uses.

  • in organic synthesis as a solvent for preparation of organometallic compounds;
  • in chemical and pharmaceutical industry as a polar, aprotic solvent, stable at high temperature and high pH values. Being mixed with other solvents, mainly other glymes, diglyme forms reaction media with a specified viscosity and permittivity constant;
  • entrainer for azeotropic distillations;

  • Manufacturer(s) no data
    Chemical structure of diglyme

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