Peracetic Acid → Adipic Acid

HRID 1274506Notes

Reaction equation

HRID 1274506 reaction equation
[C:1]([O:4][OH:5])(=[O:3])[CH3:2].[C:6]1(=[O:13])[O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C1(=O)CCCCC1.C(OCC)(=O)C>[C:6]1(=[O:13])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1.[C:1]([O:4][OH:5])(=[O:3])[CH3:2].[C:1]([OH:4])(=[O:3])[CH2:2][CH2:9][CH2:8][CH2:7][C:6]([OH:13])=[O:12]

Participants

7

Reactant 2

HCID 6585Peracetic AcidHCID 10401epsilon-CAPROLACTONE

Product 3

HCID 196Adipic AcidHCID 6585Peracetic AcidHCID 7967Cyclohexanone

Reagents, catalysts & solvents 2

HCID 7967CyclohexanoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

60 g/hour of cyclohexanone and 170.5 g/hour of a solution of ethyl acetate used as a solvent and containing 30% of peracetic acid (51.4 g/hour of pure peracetic acid which corresponds to 1.1 mole based on one mole of cyclohexanone) were introduced in a flowing-type reactor of 2 liters. The reaction was conducted under a reaction temperature of 50° C. The composition of the solution obtained was ε-caprolactone: 28.78%, unreacted cyclohexanone: 0.52%, unreacted peracetic acid: 1.31%, by-produced adipic acid: 0.59%, caprolactone polymers: 0.30%, acetic acid: 21.16% and ethyl acetate (which was the solvent): 47.34%.

Workup

  1. additionwere introduced in a flowing-type reactor of 2 liters
  2. customwas conducted under a reaction temperature of 50° C
  3. customThe composition of the solution obtained

Sources & evidence

ORD record
ord-4188c04b0eac4ad993b64ebb659f0482
Source dataset
uspto-grants-2000_12
Patent number
US06156910

Reaction notes

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