Hydrogen Peroxide → Benzoyl Peroxide

HRID 355569Notes

Reaction equation

HRID 355569 reaction equation
[OH-:1].[K+].[OH:3][OH:4].[CH3:5][C:6](NCCSP(OC)(OC)=S)=[O:7].[C:18](Cl)(=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[C:18]([O:3][O:4][C:6](=[O:7])[C:5]1[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=1)(=[O:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 7412Benzoyl chlorideHCID 14797Potassium HydroxideHCID 25815Amiphos

Product 1

HCID 7187Benzoyl PeroxideYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Giving Benzoyl Peroxide as Major Product: A beaker was loaded with 1.23 g ~85% KOH pellets (19 mmoles) dissolved up to 15.9 ml with water, 2.04 ml of 30% aqueous hydrogen peroxide (20 mmoles), 50 ml of Freon® E1, and 2.32 ml of benzoyl chloride (20 mmoles) with ice bath cooling. An ultrasonic horn connected to a 40 Khz, 150 watt Dukane power source was started up at maximum power and lowered into the reaction mixture. After 25 seconds, ultrasonication was stopped, the solids filtered off, washed with water, and sucked dry on the filter. This gave 1.52 g of white solid, a 63% yield of benzoyl peroxide based on starting benzoyl chloride. The filtrate was brought to pH ~1 by the addition of concentrated sulfuric acid and then extracted three times with methylene chloride. The three methylene chloride extracts had a combined volume of 80 ml, 10.0 ml of which took 0.2 ml of 0.1N thiosulfate in iodometric peroxide titration. The failure to find significant amounts of peroxide in the methylene chloride extracts indicates that little if any benzoyl hydroperoxide [C6H5 (C=O)OOH] was formed during the reaction.

Workup

  1. temperaturecooling
  2. customultrasonication
  3. filtrationthe solids filtered off
  4. washwashed with water
  5. customsucked dry on the filter

Sources & evidence

ORD record
ord-9b4deb3a3c5d413c8f5f06aad6b27964
Source dataset
uspto-grants-1998_11
Patent number
US05831131

Reaction notes

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