1-Butanol → Diethyl Carbonate

HRID 2115596Notes

Reaction equation

HRID 2115596 reaction equation
[O-:1][CH2:2][CH2:3][CH2:4][CH3:5].[O-:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:11]([Sn+2]CCCC)[CH2:12][CH2:13][CH3:14].[CH2:20]([OH:24])CCC.C(O)C.[C:28](=[O:30])=[O:29].C(O)C.[C:34](=[O:36])=[O:35]>>[C:28](=[O:29])([O-:30])[O:1][CH:2]([CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].[C:34](=[O:35])([O:36][CH2:11][CH2:12][CH2:13][CH3:14])[O:1][CH2:2][CH2:3][CH2:4][CH3:5].[C:20](=[O:24])([O:1][CH2:2][CH3:3])[O:6][CH2:7][CH3:8]

Participants

8

Reactant 5

HCID 2631-ButanolHCID 280Carbon Dioxide3×HCID 702EthanolHCID 19604758Methanedione--ethanol (1/1)HCID 865975583349-36-8

Product 3

HCID 7766Diethyl CarbonateHCID 68333Dibutyl carbonateHCID 86597557HCID 86597557, compound

Conditions

Temperature
150 °C

Procedure

Into a 10-ml high pressure reactor (manufactured and sold by Thar Designs Inc., U.S.A) equipped with a valve were charged 1.48 g (4 mmol) of dibutyltin dibutoxide (manufactured and sold by Aldrich, U.S.A.), 2.22 g (30 mmol) of butanol (manufactured and sold by Wako Pure Chemical Industries Ltd., Japan; a dehydrated grade), 1.38 g (30 mmol) of ethanol (manufactured and sold by Wako Pure Chemical Industries Ltd., Japan; a dehydrated grade) and a SUS ball (which was for use in stirring the contents of the reactor). The inside of the reactor was cooled to about −68° C. with a dry ice/ethanol mixture. Then, from a carbon dioxide gas bomb, 2.0 g of a high purity carbon dioxide gas, the pressure of which was lowered to about 2 MPa by means of a pressure regulator connected to the carbon dioxide gas bomb, was gently introduced into the high pressure reactor. Thereafter, the reactor was placed in an oil bath which was maintained at 150° C., and shaken for 22 hours. After that period, the inside of the reactor was cooled to about 20° C., and the internal pressure of the reactor was returned to atmospheric pressure by gently purging an excess amount of the carbon dioxide gas, thereby obtaining a transparent reaction mixture. In the reaction mixture, ethylbutyl carbonate, dibutyl carbonate and diethyl carbonate were obtained in yields of 25%, 10% and 6%, respectively.

Workup

  1. customInto a 10-ml high pressure reactor (manufactured and sold by Thar Designs Inc., U.S.A) equipped with a valve
  2. additionwas gently introduced into the high pressure reactor
  3. customThereafter, the reactor was placed in an oil bath
  4. stirringshaken for 22 hours
  5. waitAfter that period
  6. temperaturethe inside of the reactor was cooled to about 20° C.
  7. customby gently purging an excess amount of the carbon dioxide gas
  8. customobtaining a transparent reaction mixture

Sources & evidence

ORD record
ord-6a96b64cb75945a097e0182b14dfe755
Source dataset
uspto-grants-2008_10
Patent number
US07435842B2

Reaction notes

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