Phenol → Bisphenol S

HRID 1460862Notes

Reaction equation

HRID 1460862 reaction equation
[S:1](=[O:5])(=O)(O)[OH:2].[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[OH:12][C:6]1[CH:11]=[CH:10][C:9]([S:1]([C:9]2[CH:10]=[CH:11][C:6]([OH:12])=[CH:7][CH:8]=2)(=[O:5])=[O:2])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 1118Sulfuric Acid

Product 1

HCID 6626Bisphenol SYield 57.9%

Conditions

Temperature
180 °C

Procedure

102 g (1.0 mole) of 96% sulfuric acid and 546 g (6.0 moles) of phenol were simultaneously fed dropwise over a period of 30 minutes to a vertical glass tube (length 80 cm, diameter 4 cm) heated at 180° C. and packed with glass balls (diameter 4 mm). The residence time of the reaction mixture in the packed column was about 1 to 3 minutes. The effluent reaction mixture was collected and excess phenol was distilled off. The residue was dissolved in 5-10% sodium hydroxide solution and bis(4-hydroxyphenyl) sulfone was then precipitated therefrom by the addition of sulfuric acid to a pH of from 6.5 to 7.0. After filtration and drying, there were obtained 145 g (58%) of bis(4-hydroxyphenyl) sulfone 98.5% pure.

Workup

  1. customThe effluent reaction mixture
  2. customwas collected
  3. distillationexcess phenol was distilled off
  4. dissolutionThe residue was dissolved in 5-10% sodium hydroxide solution
  5. custombis(4-hydroxyphenyl) sulfone was then precipitated
  6. additionby the addition of sulfuric acid to a pH of from 6.5 to 7.0
  7. filtrationAfter filtration
  8. customdrying

Sources & evidence

ORD record
ord-ed9e1629810c49fb819b49a6491dea0a
Source dataset
uspto-grants-1991_12
Patent number
US05072049

Reaction notes

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