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.
Reactivity Profile
When the solvent, 1,2-DIMETHOXYETHANE(110-71-4), was poured into a funnel previously used to introduce the lithium aluminum hydride, a fire ignited the funnel, [MCA Case History 1182(1966)].
Air & Water Reactions
Highly flammable. Slightly soluble in water.
Hazard
Moderate fire risk.
Health Hazard
If ingested causes nausea, vomiting, cramps, weakness, coma.
Fire Hazard
Behavior in Fire: Containers may explode in fires.
Description
1,2-Dimethoxyethane (DME) is a liquid ether used as aprotic solvent. It is also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve and DME. It has the special ability to form chelates thanks to the high flexibility of its chains. Moreover, DME is the molecular model system for the poly(oxyethylene) chain. It is commonly used as a solvent in batteries and in organometallic reaction chemistry since it is higher boiling than diethyl ether and THF[1].
Chemical Properties
Colorless liquid
Uses
Monoglyme is used in the electrolyte solutions for lithium batteries.
Uses
Solvent commonly employed in organometallic reactions,1 particularly organolithium reactions.2 May also function as a ligand.3
Application
Monoglyme serves as an electrolyte solution component for lithium batteries. It is also frequently utilized as a solvent in organometallic reactions, particularly those involving organolithium compounds. Additionally, it can act as a ligand in certain chemical reactions.
Definition
ChEBI: A diether that is the 1,2-dimethyl ether of ethane-1,2-diol.
Flammability and Explosibility
Highlyflammable
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.
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.]
References
[1] Weixing Li . “The microwave spectroscopy study of 1,2-dimethoxyethane.” Journal of Molecular Spectroscopy 337 (2017): Pages 3-8.
