Diethoxymethane

Chemical Properties

colourless liquid

Uses

Diethoxymethane (DEM) is offered by Eastman Chemical Company as a cost-effective replacement solvent for monoglyme (1,2- dimethoxyethane) and methylal. The DEM diether is stable under alkaline conditions, but can be cleaved by strong acids. Diethoxymethane can be used as a chemical intermediate in many organic synthesis reactions. Diethoxymethane is useful as a solvent in lithium batteries with nonaqueous electrolytes, as a solvent for polymeric materials, and as a fuel additive. As a chemical intermediate DEM can act as an ethoxymethylating reagent for alcohols and phenols and serve as a source for formaldehyde in organic synthesis.

Uses

Diethoxymethane may be used as a substitute solvent to dichloromethane and toluene in the O-alkylation of different phenols in the presence of phase transfer catalysts (PTCs).

Synthesis Reference(s)

Synthetic Communications, 25, p. 3939, 1995 DOI: 10.1080/00397919508011470

General Description

A colorless volatile liquid with an agreeable odor. Less dense than water. Flash point below 10°F. Vapors heavier than air. May be narcotic in high concentrations. Used as a solvent and in the manufacture of cosmetics.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

DIETHOXYMETHANE, an acetal, is incompatible with strong oxidizing agents and acids. Breaks down to formaldehyde and ethanol in acidic solutions.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Highly flammable

Safety Profile

Moderately toxic by ingestion. Flammable when exposed to heat or flame; can react vigorously with oxidizers. When heated to decomposition it emits acrid smoke and irritating fumes.