Diethyl malonate

Diethyl malonate, also known as DEM, is an organic compound with the formula C5H8O4. It is a colorless, fragrant liquid that is used in organic synthesis. This compound is a diester derived from malonic acid, with the structure CH2(CO2Et)2, where Et represents the ethyl group (C2H5).

Properties

Diethyl malonate has a boiling point of 199 °C and a density of 1.055 g/cm^3. It is slightly soluble in water but highly soluble in organic solvents such as ethanol, acetone, and diethyl ether. The compound exhibits a pleasant aroma, often described as apple-like, making it a valuable additive in perfumery and flavor industries.

Synthesis

The synthesis of diethyl malonate typically involves the esterification of malonic acid. This process involves reacting malonic acid with ethanol in the presence of an acid catalyst, such as sulfuric acid, to produce diethyl malonate and water.

Applications

Diethyl malonate is a versatile compound in organic chemistry, particularly in the synthesis of other organic compounds. It is used in the Malonic ester synthesis, a method for preparing carboxylic acids. This synthesis involves the alkylation of diethyl malonate, followed by hydrolysis and decarboxylation to produce the desired carboxylic acid.

Malonic ester synthesis is particularly useful for synthesizing substituted acetic acids. Diethyl malonate is also employed in the synthesis of barbiturates, a class of drugs acting as central nervous system depressants.

Safety

Diethyl malonate is generally considered to have low toxicity, but it should be handled with care. It can cause irritation to the skin, eyes, and respiratory tract upon exposure. Proper protective equipment, such as gloves and goggles, should be used when handling this chemical.

Environmental Impact

While diethyl malonate is not classified as a major environmental pollutant, its production and use must be managed to minimize potential environmental impacts. Proper disposal methods should be followed to prevent its release into the environment.

See Also

• Organic synthesis
• Esterification
• Carboxylic acid
• Barbiturates