Phenol → Bisphenol S

HRID 1460861Notes

Reaction equation

HRID 1460861 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(O)(O)O.[S:12](=[O:16])(=O)(O)[OH:13]>O>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([S:12]([C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)(=[O:16])=[O:13])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1118Sulfuric AcidHCID 7628Boric Acid

Product 1

HCID 6626Bisphenol SYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

470.6 g (5.0 moles) of phenol and 6.2 g (0.1 mole) of boric acid were placed in a glass flask having a capacity of 2 liters. While the mixture was heated to 180°-186° C., 102.2 g (1.0 mole) of 96% sulfuric acid were added dropwise, after which the water of reaction was removed at 180°-186° C. The phenol was then distilled off over a period of 2 hours at a temperature of from 160° to 200° C. Analysis of the crude product revealed the following composition: 3% phenol, 1% isomeric sulfone and 97% bis(4-hydroxyphenyl) sulfone. Further purification was conducted as described in Example 1. There were obtained 205 g (0.82 mole; yield 82%) of bis(4-hydroxylphenyl) sulfone showing a purity of >99%.

Workup

  1. temperatureWhile the mixture was heated to 180°-186° C.
  2. customwas removed at 180°-186° C
  3. distillationThe phenol was then distilled off over a period of 2 hours at a temperature of from 160° to 200° C
  4. customFurther purification

Sources & evidence

ORD record
ord-0b48a562229a41b1bb7ffe876084cee3
Source dataset
uspto-grants-1991_12
Patent number
US05072049

Reaction notes

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