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

HRID 1913993Notes

Reaction equation

HRID 1913993 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 hydroperoxide2×HCID 14797Potassium Hydroxide2×HCID 62325Isobutyryl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent5×

Procedure

The reaction is effected in a reactor arrangement of a first reactor of type E with a downstream reactor of type C. Before the start of the reaction, the first reactor is filled with a solution of 24.4% by weight of tert-butyl hydroperoxide and 12.7% by weight of potassium hydroxide in water. 33.6 kg/h of a solution of 70% by weight of tert-butyl hydroperoxide in water, 27.2 kg/h of a solution of 45% by weight of potassium hydroxide in water, 38.0 kg/h of water and 18.4 kg/h of isobutyroyl chloride are then fed to the first reactor. Cooling with cooling water keeps the internal temperature in the first reactor at 11° C. and in the second reactor at 12° C. The reaction mixture withdrawn from the second reactor is mixed with 8.0 kg/h of isododecane and the organic phase is removed.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 a 1% by weight solution of sodium hydrogencarbonate in water, and then dried by stripping in a packed column at 20° C. and 47 mbar. 33.4 kg/h of a 75% by weight solution of tert-butyl peroxyisobutyrate in isododecane are obtained (92.8% based on isobutyroyl chloride). The space-time yield is 2.69 kg/l·h.

Workup

  1. customThe reaction is effected in a reactor
  2. customBefore the start of the reaction
  3. customat 11° C.
  4. customat 12° C
  5. customThe reaction mixture withdrawn from the second reactor
  6. additionis mixed with 8.0 kg/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 a 1% by weight solution of sodium hydrogencarbonate in water, and then dried
  10. customby stripping in a packed column at 20° C.

Sources & evidence

ORD record
ord-db7aab9b9e064b5a961a42a503074e27
Source dataset
uspto-grants-2013_12
Patent number
US08609883B2

Reaction notes

Loading…