Carbon Dioxide → Diethyl Pyrocarbonate

HRID 5749

Reaction equation

HRID 5749 reaction equation
[C:1](=[O:6])([O-:5])[O:2][CH2:3][CH3:4].[Na+:7].C(=O)([O-])[O-].C(OC([O-])=O)(=O)[O-].[O-]CC.[Na+].[Na].C(=O)=O.[Cl:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1(C)C=CC=CC=1.C(O)C>[C:1]([O:5][C:28]([O:30][CH2:31][CH3:32])=[O:29])(=[O:6])[O:2][CH2:3][CH3:4].[Cl-:27].[Na+:7]

Participants

11

Reactant 7

HCID 280Carbon DioxideHCID 10928Ethyl chloroformateHCID 19660Carbonate IonHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15238643PyrocarbonateHCID 23677505Sodium ethyl carbonate3×

Product 2

HCID 3051Diethyl PyrocarbonateHCID 5234Sodium Chloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

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.

Sources & evidence

ORD record
ord-c92cfeae8c76411db9a7c282c6b1f728
Source dataset
uspto-grants-1993_09
Patent number
US05246630

Linked notes

Loading…