Uses of Bis (2-methoxyethyl) ether

Bis (2-methoxyethyl) ether, also known as diglyme, is a linear aliphatic diether widely used as a solvent and present as a clear liquid at room temperature with a mild ether odor. The compound is notknown to occur in nature. It is synthesized from ethylene oxide and methanol in the presence of either acidic or basic catalysts. The reaction is based on the classic Williamson ether synthesis. It can also be produced from diethylene glycol and dimethyl sulfate. In June 2012, ECHA proposed addition of diglyme to the REACH very high concern list.

Uses

Bis (2-methoxyethyl) ether, due to being chemically inert and possessing excellent solvent properties, is mainly used as a solvent and an anhydrous reaction medium for organometallic synthesis. It is also used as a solubilizer.

Environmental Fate

Bis (2-methoxyethyl) ether will present as a vapor, when released to air, at a vapor pressure of 2.96 mmHg at 25°C. The vapor phase is easily degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals. The half-life for the reaction is estimated to be 22 h. Bis (2-methoxyethyl) ether does not contain chromophores that will absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.
Bis (2-methoxyethyl) ether has very high mobility in soil based on the estimated Koc of 15, when released to soil. It may volatilize from dry soil surfaces based upon its vapor pressure. Aquatic fate: Bis (2-methoxyethyl) ether does not absorb to suspended solids and sediments when released into water. Hydrolysis is not an important environmental matter because bis (2-methoxyethyl) ether does not contain a functional group that can hydrolyze under environmental conditions.

Mechanism of Toxicity 

The metabolite 2-methoxyacetic acid, which is generated from 2-methroxyethanol by the reaction of alcohol dehydrogenase, may be important for the toxic effects. It can undergo activation to methoxyacetyl coenzyme A and enter the Krebs cycle or fatty acid biosynthesis. Several metabolites of 2-methoxyethanol, such as 2-methoxy-N-acetyl glycine, have been identified that support this pathway. Thus, 2-methoxyacetic acid may interfere with essential metabolic pathways of the cell, and it was hypothesized that this causes the testicular lesions and malformations in experimental animals.