tert-Butyl hydroperoxide → Propaneperoxoic acid, 2-methyl-, 1,1-dimethylethyl ester

HRID 1913992Notes

Reaction equation

HRID 1913992 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[C:9](Cl)(=[O:13])[CH:10]([CH3:12])[CH3:11]>O>[C:9]([O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:13])[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 14797Potassium HydroxideHCID 62325Isobutyryl chloride

Product 1

HCID 61023Propaneperoxoic acid, 2-methyl-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The reaction is effected in a reactor arrangement of a first reactor of type D with two reactors of type B connected downstream in series. 1.22 kg/l·h of a 26% by weight solution of tert-butyl hydroperoxide and 17% by weight of potassium hydroxide in water and 0.32 kg/l·h of isobutyroyl chloride are fed to the first reactor. The metering rates are based on the total volume of the reactor arrangement in litres. Cooling with cooling water keeps the internal temperature in the first reactor at 26° C. and in the two downstream reactors at 20° C. The reaction mixture withdrawn from the third reactor is mixed with 0.79 kg/l·h of demineralized water and 0.14 kg/l·h of isododecane, and the organic phase is removed. The organic phase is washed successively with an 8% by weight solution of sodium hydroxide in water, with a solution of 10% by weight of sodium sulphite in water comprising acetic acid and with demineralized water, and then dried with calcium chloride. 0.54 kg/l·h of a 75% by weight solution of tert-butyl peroxyisobutyrate in isododecane is obtained (86.0% based on isobutyroyl chloride).

Workup

  1. customThe reaction is effected in a reactor
  2. customarrangement of a first reactor of type D with two reactors of type B connected downstream in series
  3. customat 26° C.
  4. customat 20° C
  5. customThe reaction mixture withdrawn from the third reactor
  6. additionis mixed with 0.79 kg/l·h of demineralized water and 0.14 kg/l·h of isododecane
  7. customthe organic phase is removed
  8. washThe organic phase is washed successively with an 8% by weight solution of sodium hydroxide in water, with a solution of 10% by weight of sodium sulphite in water
  9. dry with materialwith demineralized water, and then dried with calcium chloride
  10. customis obtained (86.0% based on isobutyroyl chloride)

Sources & evidence

ORD record
ord-dec9501fbb9a49e4bb2a9b739b7c0397
Source dataset
uspto-grants-2013_12
Patent number
US08609883B2

Reaction notes

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