Phenol → Oxalic acid, diphenyl ester

HRID 356232Notes

Reaction equation

HRID 356232 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:14][CH3:15])(=[O:13])[C:9](OC)=[O:10]>O([Ti](OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1)C1C=CC=CC=1>[C:8]([O:14][C:15]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)(=[O:13])[C:9]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10]

Participants

4

Reactant 2

HCID 996Phenol2×HCID 11120Dimethyl oxalate2×

Product 1

HCID 18475Oxalic acid, diphenyl ester

Reagents, catalysts & solvents 1

HCID 178420525HCID 178420525, compoundCatalyst

Conditions

Temperature
190 °C

Procedure

A solution comprising 54.1% by weight of phenol, 45.3% by weight of dimethyl oxalate and 0.5% by weight of tetraphenoxytitanium was fed into the twelfth step from the top of a first fifty-plate Oldershaw-type reactive distillation column provided with a one liter bottom flask and having an inner diameter of 32 mm, at a flow rate of 600 ml/hr, and the bottom flask was heated by a mantle heater to a temperature of 190° C., while withdrawing a resultant vapor fraction from the top portion of the first column at a reflux ratio of 2 and condensing the withdrawn vapor fraction by a cooler, to transesterify dimethyl oxalate with phenol and to produce diphenyl oxalate.

Workup

  1. distillationwas fed into the twelfth step from the top of a first fifty-plate Oldershaw-type reactive distillation column
  2. customprovided with a one liter bottom flask
  3. customwhile withdrawing a resultant vapor fraction from the top portion of the first column
  4. customat a reflux ratio of 2 and condensing the withdrawn vapor fraction by a cooler

Sources & evidence

ORD record
ord-87c2af0f2e534f4e8e9b7bb2f3b95c78
Source dataset
uspto-grants-1998_11
Patent number
US05834615

Reaction notes

Loading…