Reaction #5845

ord-c92cfeae8c76411db9a7c282c6b1f728

Reaction equation

CC[O-].[Na+]
sodium ethoxide
O=C=O
carbon dioxide
CCOC(=O)[O-].[Na+]
sodium ethyl carbonate
CCOC(=O)[O-].[Na+]
sodium ethyl carbonate
CCOC(=O)Cl
ethyl chloroformate
O=C([O-])OC(=O)[O-]
pyrocarbonate
O=C([O-])[O-]
carbonate
[Na]
sodium
CCOC(=O)[O-].[Na+]
sodium ethyl carbonate
CCOC(=O)OC(=O)OCC
diethyl pyrocarbonate
[Cl-].[Na+]
sodium chloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

The organic pyrocarbonates may be prepared by reacting alkali metal organic carbonate, e.g., sodium ethyl carbonate, with organic halocarbonate, e.g., ethyl chlorocarbonate (ethyl chloroformate). The organo groups of the organic carbonate and halocarbonate are chosen to correspond to the organo groups desired for the pyrocarbonate. For example, sodium ethoxide, which can be prepared by dissolving sodium metal in a toluene solution of ethyl alcohol, is carbonated with carbon dioxide to prepare sodium ethyl carbonate. Thereafter, the sodium ethyl carbonate is reacted with ethyl chloroformate to form diethyl pyrocarbonate and sodium chloride. The chloride salt is filtered and the pyrocarbonate recovered by distillation.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246630uspto-grants-1993_09