Phenol → Diphenyl carbonate

HRID 260560

Reaction equation

HRID 260560 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]>[O-2].[O-2].[Ti+4]>[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 996Phenol2×HCID 6371PhosgeneHCID 15891Phenyl chloroformate

Product 1

HCID 7597Diphenyl carbonateYield 2,036%

Reagents, catalysts & solvents 1

HCID 162651Titanium oxide (Ti3O)Catalyst

Procedure

In a plane-joint jar with flow spoilers, a gas-dispersion stirrer and reflux condenser, 0.75 mol/h phosgene was continuously bubbled into 141 g (1.50 moles) of phenol at 140° C. in the presence of 14.1 g (10 wt % relative to phenol) of a powdered titanium dioxide from the Riedel de Haen company. After about 2 h reaction time, the phenol conversion was 12.5%, whereby 0.7 g phenyl chloroformate and 19.5 g diphenyl carbonate were formed. The selectivity to carbonate esters was >99%.

Workup

  1. temperatureIn a plane-joint jar with flow spoilers, a gas-dispersion stirrer and reflux condenser
  2. customAfter about 2 h reaction time

Sources & evidence

ORD record
ord-c77c45f7d13644d3954aed53fde719d7
Source dataset
uspto-grants-1996_06
Patent number
US05527942

Linked notes

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