Hydrochloric Acid → tert-Butyl peroxybenzoate

HRID 909416Notes

Reaction equation

HRID 909416 reaction equation
[C:1]([O:5][OH:6])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>O>[C:9]([O:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6410tert-Butyl hydroperoxide2×HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 11966tert-Butyl peroxybenzoateYield 95.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent5×

Procedure

Before the start of the reaction, the loop reactor is filled with a solution of 19.6% by weight of tert-butyl hydroperoxide and 9.0% by weight of sodium hydroxide. Initially 18.4 kg/h of a solution of 70% by weight of tert-butyl hydroperoxide in water, 11.8 kg/h of a solution of 50% by weight of sodium hydroxide in water, 35.2 kg/h of water and 18.0 kg/h of benzoyl chloride are then fed to the loop reactor. Cooling with cooling water keeps the internal temperature at 12° C. in the loop reactor and at 11° C. in the stirred cell reactor. The partial neutralization is effected with 2.2 kg/h of 31% by weight hydrochloric acid with addition of 6.0 kg/h of water at a temperature of 16° C. The organic phase is extracted with 17.2 kg/h of a 15% by weight aqueous solution of sodium hydroxide. This affords 18.4 kg/h of aqueous extract comprising 6.3% by weight of tert-butyl hydroperoxide and 14.1% by weight of sodium hydroxide, which are feeded into the loop reactor. From the time at which aqueous extract is recycled into the loop reactor, the metered addition of the feedstocks is changed to 16.8 kg/h of a solution of 70% by weight of tert-butyl hydroperoxide in water, 6.6 kg/h of a solution of 50% by weight of sodium hydroxide in water and 23.0 kg/h of water. After the extraction, the organic phase is washed with 36 kg/h of a solution of 1% by weight of sodium sulphite and 0.4% by weight of sulphuric acid, and dried by stripping at 35° C. and 43 mbar. 23.8 kg/h of tert-butyl peroxybenzoate with a purity of 99.7% are obtained (95.3% yield based on benzoyl chloride).

Workup

  1. customBefore the start of the reaction
  2. customat 12° C.
  3. customat 11° C.
  4. extractionThe organic phase is extracted with 17.2 kg/h of a 15% by weight aqueous solution of sodium hydroxide
  5. extractionThis affords 18.4 kg/h of aqueous extract
  6. extractionFrom the time at which aqueous extract
  7. additionthe metered addition of the feedstocks
  8. extractionAfter the extraction
  9. washthe organic phase is washed with 36 kg/h of a solution of 1% by weight of sodium sulphite and 0.4% by weight of sulphuric acid
  10. customdried
  11. customby stripping at 35° C.

Sources & evidence

ORD record
ord-200c963cfd4f4910997b49faba4fbda0
Source dataset
uspto-grants-2011_09
Patent number
US08017801B2

Reaction notes

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