dimethyl carbonate (dmc)
CAS no. 616-38-6
Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from classification as a Volatile organic compound (VOC) in the US. Dimethyl carbonate is often considered to be a green reagent.
Dimethyl carbonate can be prepared by the reaction of phosgene with methanol via methyl chloroformate:
COCl2 + CH3OH → CH3OCOCl + HCl
CH3OCOCl + CH3OH → CH3OCO2CH3 + HCl
COCl2 + 2 CH3OH → CH3OCO2CH3 + 2 HCl
This historical synthesis process is undesirable because of phosgene's toxicity and has been largely replaced by other synthesis routes. It is produced industrially by a transesterification of propylene carbonate and methanol, which also affords propylene glycol. A second large scale commercial synthesis route uses a process where carbon monoxide, methanol and oxygen are reacted to form dimethyl carbonate. World production in 1997 was estimated at 1000 barrels a day. Production of dimethyl carbonate worldwide is limited to Asia and Europe.
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