Phenol → Diphenyl carbonate

HRID 1489890Notes

Reaction equation

HRID 1489890 reaction equation
C(Cl)(Cl)=O.[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]>C.[Ti]>[C:13](=[O:14])([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 996Phenol3×HCID 6371PhosgeneHCID 15891Phenyl chloroformate

Product 1

HCID 7597Diphenyl carbonateYield 52,440.5%

Reagents, catalysts & solvents 1

HCID 159433Methane--titanium (1/1)Catalyst

Procedure

0.42 mol/h of phosgene were continuously passed through 141 g (1.50 mol) of phenol in the presence of 14.1 g (10 wt. % relative to the phenol) of a powdered titanium carbide from H. C. Starck at 140° C. in a plane ground joint flask equipped with flow spoilers, a gas-dispersion stirrer and reflux condenser. After approximately 2 hours' reaction time, phenol conversion was 18.2%, wherein 0.04 g of phenyl chloroformate and 28.7 g of diphenyl carbonate were formed. Selectivity for carbonates was approximately 99%.

Workup

  1. customStarck at 140° C. in a plane ground joint flask equipped with flow spoilers, a gas-dispersion stirrer
  2. temperaturereflux condenser

Sources & evidence

ORD record
ord-e2f61145e7184e6084d6958a61825aa6
Source dataset
uspto-grants-1997_10
Patent number
US05679825

Reaction notes

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