Phenol → Phenol

HRID 21852

Reaction equation

HRID 21852 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(CC2C=CC=CC=2)C=CC=CC=1.[PH2](O)=O.[C:24](Cl)(Cl)=[O:25].[C:28](Cl)([Cl:30])=[O:29].[C:32]1([OH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[C:24](=[O:25])([O:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([O:7][C:28]([Cl:30])=[O:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 6371PhosgeneHCID 7580DiphenylmethaneHCID 4124402Phosphinic AcidHCID 86748739Phosgene phenol

Product 3

HCID 996PhenolHCID 7597Diphenyl carbonateHCID 15891Phenyl chloroformate

Conditions

Temperature
120 °C

Procedure

The reactor of Example 1 is charged with phenol (319.0 g, 3.390 mol), diphenylmethane as an internal GC standard (3.0723 g), and 50 weight percent hypophosphorous acid (7.046 g). Phosgene (64.6 g, 0.65 mol) is passed into the reactor for 90 min. Phosgene/phenol molar ratio is 0.19. After heating at 120° C. an additional 4 hr the reactor is cooled to ambient temperature. Analysis by GC yields diphenyl carbonate (29.1 mmol), phenylchloroformate (156.7 mmol) and phenol (2.96 mol). Selectivity to phenylchloroformate is 36 mole percent based on phenol, 24 mole percent based on phosgene. Part of the phenol is consumed in a reaction with hypophosphorous acid to yield triphenyl phosphate.

Workup

  1. temperatureis cooled to ambient temperature

Sources & evidence

ORD record
ord-076d81faa0854800bc12fb85d8d57f50
Source dataset
uspto-grants-1995_06
Patent number
US05424473

Linked notes

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