Hydrochloric Acid → 4,4'-Dichlorodiphenyl sulfone

HRID 637809Notes

Reaction equation

HRID 637809 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=O)=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ClS(O)(=O)=O.Cl>O>[CH:6]1[C:5]([S:8]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=2)(=[O:10])=[O:11])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7400p-Chlorobenzenesulfonic acidHCID 7964Chlorobenzene2×HCID 24638Chlorosulfonic acid

Product 1

HCID 66254,4'-Dichlorodiphenyl sulfoneYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 211 g (1.1 moles) quantity of 4-chlorobenzenesulfonic acid was added to 112 g (1 mole) of chlorobenzene and the mixture was cooled with water while 123 g (1.1 moles) of chlorosulfonic acid was added to the mixture at about 10° to about 20° C. over a period of 1 hour. After the addition, the reaction mixture was stirred for 3 hours while being maintained at 20° to 30° C. The hydrochloric acid gas evolved during the reaction was continuously removed from the reaction system. After the termination of the reaction, about 400 ml of water was added to the reaction mixture and 11.2 g (0.1 mole) of the unreacted chlorobenzene was recovered by distillation. The separation of the precipitate formed gave 77 g of 4,4'-dichlorodiphenylsulfone in a yield of 60% (based on the amount of the aromatic hydrocarbon as consumed, the same hereinafter). M.P. 148.5° to 149.5° C. Purity of 99.8% (according to liquid chromatography, the same hereinafter).

Workup

  1. additionwas added to the mixture at about 10° to about 20° C. over a period of 1 hour
  2. additionAfter the addition
  3. temperaturewhile being maintained at 20° to 30° C
  4. customwas continuously removed from the reaction system
  5. customAfter the termination of the reaction, about 400 ml of water
  6. distillationwas recovered by distillation
  7. customThe separation of the precipitate
  8. customformed

Sources & evidence

ORD record
ord-24ec0dc0f8d645899e48c7e63fd2506a
Source dataset
uspto-grants-1985_12
Patent number
US04558161

Reaction notes

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