Hydrochloric Acid → HCID 18959084, compound

HRID 909412Notes

Reaction equation

HRID 909412 reaction equation
[C:1]([O:5]O)([CH3:4])([CH3:3])[CH3:2].[OH-:7].[K+].[CH2:9]([CH:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12](Cl)=[O:13])[CH3:10].Cl.[OH2:20]>>[CH3:18][CH2:17][CH2:16][CH:15]1[O:20][O:7][C:11]1([C:12]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:13])[CH2:9][CH3:10]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962Water5×HCID 6410tert-Butyl hydroperoxide2×HCID 14797Potassium Hydroxide2×HCID 791032-Ethylhexanoyl chloride

Product 1

HCID 18959084HCID 18959084, compoundYield 98.5%

Procedure

Before the start of the reaction, the loop reactor is filled with a solution of 25.8% by weight of tert-butyl hydroperoxide and 16.4% by weight of potassium hydroxide. Initially 24.6 kg/h of a solution of 70% by weight of tert-butyl hydroperoxide in water, 24.0 kg/h of a solution of 45% by weight of potassium hydroxide in water, 17.4 kg/h of water and 24.0 kg/h of 2-ethylhexanoyl chloride are then fed to the loop reactor. Cooling with cooling water keeps the internal temperature at 35° C. in the loop reactor and at 27° C. in the stirred cell reactor. The partial neutralization is effected with 5.4 kg/h of 31% by weight hydrochloric acid with addition of 6.0 kg/h of water at a temperature of 18° C. The organic phase is extracted with 26.0 kg/h of a 15% by weight aqueous solution of potassium hydroxide. This affords 29.2 kg/h of aqueous extract comprising 10.8% by weight of tert-butyl hydroperoxide and 13.4% by weight of potassium hydroxide, which are feeded into the loop reactor. From the time at which the aqueous extract is recycled into the loop reactor, the metered addition of the feedstocks is changed to 20.0 kg/h of a solution of 70% by weight of tert-butyl hydroperoxide in water, 15.4 kg/h of a solution of 45% by weight of potassium hydroxide in water and 1.4 kg/h of water. After the extraction, the organic phase is washed with 36.0 kg/h of a solution of 1% by weight of sodium sulphite and 0.2% by weight of sulphuric acid, and dried by stripping at 33° C. and 40 mbar. 31.6 kg/h of tert-butyl peroxy-2-ethylhexanoate are obtained with a purity of 99.3% (98.5% yield based on 2-ethylhexanoyl chloride).

Workup

  1. customBefore the start of the reaction
  2. customat 35° C.
  3. customat 27° C.
  4. extractionThe organic phase is extracted with 26.0 kg/h of a 15% by weight aqueous solution of potassium hydroxide
  5. extractionThis affords 29.2 kg/h of aqueous extract
  6. extractionFrom the time at which the aqueous extract
  7. additionthe metered addition of the feedstocks
  8. extractionAfter the extraction
  9. washthe organic phase is washed with 36.0 kg/h of a solution of 1% by weight of sodium sulphite and 0.2% by weight of sulphuric acid
  10. customdried
  11. customby stripping at 33° C.

Sources & evidence

ORD record
ord-27e0d2be77114877b4220096384bc832
Source dataset
uspto-grants-2011_09
Patent number
US08017801B2

Reaction notes

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