Hydrogen Peroxide → 1,3-Di(ethenesulfonyl)-2,2-bis[(ethenesulfonyl)methyl]propane

HRID 371900Notes

Reaction equation

HRID 371900 reaction equation
P(=O)(O)(O)O.OO.Cl[CH2:9][CH2:10][S:11]([CH2:14][C:15]([CH2:30][S:31]([CH2:34][CH2:35]Cl)(=[O:33])=[O:32])([CH2:23][S:24]([CH2:27][CH2:28]Cl)(=[O:26])=[O:25])[CH2:16][S:17]([CH2:20][CH2:21]Cl)(=[O:19])=[O:18])(=[O:13])=[O:12]>>[CH:34]([S:31]([CH2:30][C:15]([CH2:16][S:17]([CH:20]=[CH2:21])(=[O:18])=[O:19])([CH2:14][S:11]([CH:10]=[CH2:9])(=[O:13])=[O:12])[CH2:23][S:24]([CH:27]=[CH2:28])(=[O:26])=[O:25])(=[O:32])=[O:33])=[CH2:35]

Participants

4

Reactant 3

HCID 784Hydrogen PeroxideHCID 1004Phosphoric AcidHCID 20351957HCID 20351957, compound

Product 1

HCID 155967151,3-Di(ethenesulfonyl)-2,2-bis[(ethenesulfonyl)methyl]propane

Procedure

To 400 parts of ethanol were successively added 9.2 parts of metallic sodium, 31.2 parts of 2-mercaptoethanol amd 38.8 parts of pentaerythritol tetrabromide, and the resulting mixture was heated under reflux. Thereafter, the deposited sodium bromide was removed, and the ethanol was removed by distillation to obtain tetrakis(2-hydroxyethylthiomethyl)methane. This compound was added to 80 parts of chloroform, and 60 parts of thionyl chloride was dropped into the resulting mixture. Subsequently, the mixture was heated under reflux, and then the solvent chloroform and unreacted thionyl chloride were removed by distillation under reduced pressure. The residual oily substance was poured into ice water and extracted with ether, and the ether extract was dehydrated over anhydrous sodium sulfate and then freed from the ether by distillation to obtain tetrakis(2-chloroethylthiomethyl)methane. To this compound were successively added 0.4 part of phosphoric acid and 80 parts of 30% aqueous hydrogen peroxide, and the resulting mixture was heated under reflux and then cooled to deposit tetrakis(2-chloroethylsulfonylmethyl)methane. The deposited compound was recovered by filtration and dissolved in 200 parts of acetone, and the resulting solution was incorporated with 40 parts of triethylamine and then stirred at room temperature to deposit triethylamine hydrochloride. This hydrochloride was removed, and the acetone was removed by distillation to deposit solids. The deposited solids were recrystallized from acetone-ethanol to obtain tetrakis(vinylsulfonylmethyl)methane.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux
  3. temperaturecooled
  4. filtrationThe deposited compound was recovered by filtration
  5. dissolutiondissolved in 200 parts of acetone
  6. customThis hydrochloride was removed
  7. customthe acetone was removed by distillation to deposit solids
  8. customThe deposited solids were recrystallized from acetone-ethanol

Sources & evidence

ORD record
ord-6157a42d80bc4f37b45b4eec9db508d3
Source dataset
uspto-grants-1978_05
Patent number
US04088495

Reaction notes

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