Dimethyl carbonate
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| Names | |
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IUPAC name
Dimethyl carbonate
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| Other names
DMC
Methyl carbonate |
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| Identifiers | |
616-38-6 
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| 3D model (Jmol) | Interactive image |
| ChEBI |
CHEBI:36596
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| ChemSpider |
11526
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| ECHA InfoCard | 100.009.527 |
| PubChem | 12021 |
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| Properties | |
| C3H6O3 | |
| Molar mass | 90.08 g·mol−1 |
| Appearance | Clear liquid |
| Density | 1.069-1.073 g/mL |
| Melting point | 2 to 4 °C (36 to 39 °F; 275 to 277 K) |
| Boiling point | 90 °C (194 °F; 363 K) |
| 13.9 g/100 mL | |
| Hazards | |
| Main hazards | Flammable |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
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 the restrictions placed on most volatile organic compounds (VOCs) 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:
Overall:
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 ethylene carbonate or propylene carbonate and methanol, which also affords respectively ethylene glycol or 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, the middle east and Europe.
Dimethyl carbonate methylates anilines, phenols and carboxylic acids, but many of these reactions require the use of an .
Dimethyl carbonate's main benefit over other methylating reagents such as iodomethane and dimethyl sulfate is its much lower toxicity and its biodegradability. Unfortunately, it is a relatively weak methylating agent compared to these traditional reagents.
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