1,2-Dimethoxyethane (EDM)

Synthesis

1,2-Dimethoxyethane is derived from the reaction of ethylene glycol monomethyl ether with sodium metal and methyl chloride. The ethylene glycol monomethyl ether and the metal sodium were refluxed together until the metal sodium was completely reacted, the temperature was lowered to 45° C., and methyl chloride was introduced. After the reaction is completed, fractional distillation is performed to collect fractions at 84-85.5°C to obtain 1,2-Dimethoxyethane.

Definition

ChEBI: A diether that is the 1,2-dimethyl ether of ethane-1,2-diol.

General Description

A liquid with a sharp odor. Less dense than water. Flash point 34°F. Mildly toxic by ingestion and inhalation. Severely irritates skin and eyes. Vapors heavier than air. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

When the solvent, 1,2-Dimethoxyethane, was poured into a funnel previously used to introduce the lithium aluminum hydride, a fire ignited the funnel, [MCA Case History 1182(1966)].

Hazard

Moderate fire risk.

Health Hazard

If ingested causes nausea, vomiting, cramps, weakness, coma.

Fire Hazard

Behavior in Fire: Containers may explode in fires.

Flammability and Explosibility

Highlyflammable

Safety Profile

An experimental teratogen. Other experimental reproductive effects. Readdy forms an explosive peroxide. A very dangerous fire hazard when exposed to heat, flame, or oxidzers. Mixture with lithium tetrahydroaluminate may ignite orexplode if heated. When heated to decomposition it emits acrid smoke and fumes. See also GLYCOL ETHERS.

Purification Methods

Traces of water and acidic materials have been removed from it by refluxing with Na, K or CaH2, decanting and distilling from Na, K, CaH2 or LiAlH4. The reaction has been speeded up by using vigorous high-speed stirring with molten potassium. For virtually complete elimination of water, 1,2-dimethoxyethane has been dried with Na-K alloy until a characteristic blue colour is formed in the solvent at Dry-ice/cellosolve temperatures: the solvent is kept with the alloy until distilled for use [Ward J Am Chem Soc 83 1296 1961]. Alternatively, glyme, refluxed with benzophenone and Na-K, is dry enough if, on distillation, it gives a blue colour of the ketyl immediately on addition to benzophenone and sodium [Ayscough & Wilson J Chem Soc 5412 1963]. It has also been purified by distillation under N2 from sodium benzophenone ketyl (see above). [Beilstein 1 IV 2376.]