What Is Diethyl Carbonate?
Diethyl carbonate, a neutral ester of carbonic acid, emits an ethereal odor and appears as a colorless liquid at room temperature. Due to its low flash point, it is classified as a hazardous and inflammable substance under various safety laws, necessitating careful handling.
Uses of Diethyl Carbonate
This compound finds application as a solvent for nitrocellulose, and synthetic resins, and as a reaction solvent, cleaning, and stripping agent. It is notably used as an electrolyte solvent for lithium-ion batteries, in organic synthesis for ethoxycarbonylation, and as a raw material in the production of polycarbonates and polyurethanes. Additionally, it facilitates C-alkoxycarbonylation reactions and the formation of 2-oxazolidinone from 1,2-amino alcohols.
Properties of Diethyl Carbonate
With a melting point of -43°C and a boiling point between 126-128°C, diethyl carbonate is insoluble in water yet soluble in organic solvents like ethanol, chloroform, and ether. It boasts a flash point of 25°C, an ignition point of 445°C, and a molar mass of 118.13 g/mol. Its density is 0.975 g/cm3.
Other Information on Diethyl Carbonate
1. Synthesis with Phosgene or Urea
Diethyl carbonate can be synthesized through the reaction of phosgene and ethanol, producing hydrogen chloride as a byproduct. Alternatively, it can be generated from urea and ethanol, with ethyl carbamate forming as an intermediate. This process requires a heterogeneous catalyst that acts as both a Lewis acid and a base.
2. Other Synthetic Methods
Other methods include the reaction of silver carbonate with ethyl iodide, oxidative carbonylation with carbon monoxide and ethanol, and transesterification from dimethyl carbonate. Additionally, it can be produced using ethyl nitrite and carbon monoxide with a palladium catalyst.
3. Related Compounds
As a type of carbonate ester, diethyl carbonate is related to dimethyl carbonate, diphenyl carbonate, and cyclic esters like ethylene carbonate and propylene carbonate.