Carbon Dioxide → Diphenyl carbonate

HRID 654577Notes

Reaction equation

HRID 654577 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]1([O:14][C:15]2C=CC=CC=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)=[O:22].O=O.[C]=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C([O-])(=O)C.[Co+2].C1(=O)C=CC(=O)C=C1>[C:15](=[O:22])([O:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

10

Reactant 5

HCID 280Carbon DioxideHCID 977Oxygen3×HCID 996PhenolHCID 7583Diphenyl EtherHCID 178418416HCID 178418416, compound3×

Product 1

HCID 7597Diphenyl carbonateYield 194.2%

Reagents, catalysts & solvents 4

HCID 4650QuinoneCatalystHCID 6277Cobalt diacetateCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

The procedure of Example 1 was repeated except there was utilized 50.5 gram of phenol, 4.46 grams of diphenylether, 0.275 grams of benzoquinone. 1.5 grams of tetrabutylammonium bromide, 0.062 gram of palladium diacetate, and 0.042 gram of cobalt diacetate. The reactor vessel was then again sealed and purged with 4 times 600 psi of carbon dioxide. The reaction vessel was then charged with 620 psi of carbon dioxide (0.431 mole), 380 psi of oxygen and 800 of psi of carbon monoxide, to provide a total pressure at room temperature of about 1800 psi. The reactor was then heated to 100° C. After one hour, the reactor was depressurized to 1000 psi and then recharged with 380 psi of oxygen and 760 psi of carbon monoxide to produce a total pressure of 2140 psi. After 2 hours of reaction, the reaction vessel was exhausted to 900 psi then repressurized with 450 psi of oxygen and 700 psi of carbon monoxide to provide a total pressure at 100° C. of 2050 psi. The reactor was then allowed to cool to room temperature after 3 hours of reaction. There was obtained 10.9 grams of diphenyl carbonate or a 19% yield.

Workup

  1. customThe reactor vessel was then again sealed
  2. custompurged with 4 times 600 psi of carbon dioxide
  3. customto provide a total pressure at room temperature of about 1800 psi
  4. customto produce a total pressure of 2140 psi
  5. customAfter 2 hours of reaction
  6. customto provide a total pressure at 100° C. of 2050 psi
  7. temperatureto cool to room temperature after 3 hours of reaction

Sources & evidence

ORD record
ord-b4492a7fec9f4f3494b3fcf1b49b10bd
Source dataset
uspto-grants-1992_07
Patent number
US05132447

Reaction notes

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