Phenol → Bisphenol S

HRID 971974Notes

Reaction equation

HRID 971974 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:8](=[O:12])(=O)(O)[OH:9].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1Cl.[OH-:21].[Na+]>O>[CH:6]1[C:1]([OH:7])=[CH:2][CH:3]=[C:4]([S:8]([C:18]2[CH:19]=[CH:14][C:15]([OH:21])=[CH:16][CH:17]=2)(=[O:12])=[O:9])[CH:5]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 72391,2-Dichlorobenzene2×HCID 14798Sodium Hydroxide

Product 1

HCID 6626Bisphenol SYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 343 g (3.69 moles) of phenol, 146 g (1.46 moles) of 98% sulfuric acid and 300 g of o-dichlorobenzene is heated with stirring. When the temperature of the reaction system reaches about 140° C., the mixture begins to boil, giving off an azeotropic mixture of water and o-dichlorobenzene, which is condensed and separated into two phases, i.e., water and o-dichlorobenzene. The o-dichlorobenzene is continuously returned to the reaction mixture. With continuous heating, when the amount of the aqueous phase reaches 55 ml, the temperature of reaction mixture is about 184° C. Subsequently o-dichlorobenzene containing small amounts of water and phenol is completely distilled off over a period of 3 hours by reducing a pressure of the reaction system to produce the dried reaction mixture in a solid state, while adjusting the temperature to 180° to 190° C. A solution of 62 g of sodium hydroxide in 3.5 l of water is added to the residue, 5 g of active carbon is added to the solution, the mixture is filtered and the filtrate is neutralized with sulfuric acid. The resulting crystals are filtered off, then washed with water and dried, giving 338 g of 4,4'-dihydroxydiphenylsulfone, melting at 248.5° C., in a yield of 92.6% based on the sulfuric acid starting material. When analyzed by gas chromatography, the isomer content is found to be 0.6% in the dried reaction mixture and 0.5% in the product.

Workup

  1. temperatureis heated
  2. customreaches about 140° C.
  3. customgiving off
  4. customcondensed
  5. customseparated into two phases, i.e., water and o-dichlorobenzene
  6. customthe temperature of reaction mixture
  7. customis about 184° C
  8. distillationSubsequently o-dichlorobenzene containing small amounts of water and phenol is completely distilled off over a period of 3 hours
  9. customto produce
  10. customthe dried reaction mixture in a solid state
  11. customto 180° to 190° C
  12. additionis added to the solution
  13. filtrationthe mixture is filtered
  14. filtrationThe resulting crystals are filtered off
  15. washwashed with water
  16. customdried

Sources & evidence

ORD record
ord-9405be067c6946af8ad8b8dbb5a6e259
Source dataset
uspto-grants-1979_07
Patent number
US04162270

Reaction notes

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