Dimethyl Sulfate → 4,4'-Dichlorodiphenyl sulfone

HRID 1090857Notes

Reaction equation

HRID 1090857 reaction equation
[S:1](=[O:4])(=O)=[O:2].S(OC)(OC)(=O)=O.S(OS(OC)(=O)=O)(OC)(=O)=O.[Cl:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:1]([C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=2)(=[O:4])=[O:2])=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 6497Dimethyl SulfateHCID 7964ChlorobenzeneHCID 24682Sulfur trioxideHCID 12591487Dimethyl disulfate

Product 1

HCID 66254,4'-Dichlorodiphenyl sulfone

Procedure

When the components are passed once through the reactor at a rate giving a residence time of from 1 to 3 minutes, the conversion rate is 57%. This can be increased to 91% conversion by continuously pumping the effluent reaction mixture back to the fixed bed of the reactor to give an average residence time of approximately 15 minutes. No advantage is gained, we have found, by first converting sulfur trioxide and dimethyl sulfate to reactive dimethyl pyrosulfate and then reacting the latter with chlorobenzene. Precipitating the product in chlorobenzene instead of aqueous sulfuric acid gives bis(4-chlorophenyl) sulfone having a purity of >99.5%.

Workup

  1. customgiving a residence time of from 1 to 3 minutes
  2. temperatureThis can be increased to 91% conversion
  3. customthe effluent reaction mixture back to the fixed bed of the reactor
  4. customto give an average residence time of approximately 15 minutes
  5. customPrecipitating the product in chlorobenzene instead of aqueous sulfuric acid

Sources & evidence

ORD record
ord-9ce9ada515eb49db805322e5b77fe0b7
Source dataset
uspto-grants-1992_01
Patent number
US05082973

Reaction notes

Loading…