Peracetic Acid → Phenol

HRID 1438866Notes

Reaction equation

HRID 1438866 reaction equation
[C:1]1(=[O:8])O[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(OO)(=O)C.C(OO)(=O)C.CC(C)=O.C1(=O)NCCCCC1>C(O)(=O)C.CC(C)=O>[C:1]1(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 5

HCID 6585Peracetic Acid2×HCID 7768CaprolactamHCID 7967Cyclohexanone3×HCID 10401epsilon-CAPROLACTONE3×HCID 86735040HCID 86735040, compound

Product 2

HCID 996PhenolHCID 7967Cyclohexanone

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 180AcetoneSolvent

Procedure

The epsilon caprolactone employed in accordance with the invention is available commercially so that neither the compound per se nor the method by which it is obtained constitutes any portion of the invention. According to one method, epsilon caprolactone is prepared by oxidizing cyclohexanone with an anhydrous solution of peracetic acid and acetone. The product thus obtained comprises acetic acid and epsilon caprolactone. When this method is used, it is desirable to add the peracetic acid-acetone solution to an excess of the cyclohexanone, e.g., 5 to 1 molar ratio of cyclohexanone to peracetic acid, in a vessel maintained under reflux. The epsilon caprolactone is recovered from the vessel by conventional distillation. The cyclohexanone used in the preparation of epsilon caprolactone is an intermediate product in the preparation of caprolactam. Cyclohexanone can be obtained either by the hydrogenation of phenol or the oxidation of cyclohexane. If a commercially available epsilon caprolactone is used in accordance with the invention, I prefer to purify the material by vacuum distillation. According to a typical purification procedure, epsilon caprolactone is subjected to distillation in a vacuum distillation column, separately collecting that portion boiling at 56° to 57° C./0.4 torr. Epsilon caprolactone is water-white with a single gas-chromatography peak.

Workup

  1. customthe method by which it is obtained
  2. customis prepared
  3. customThe product thus obtained
  4. temperaturein a vessel maintained
  5. temperatureunder reflux
  6. distillationThe epsilon caprolactone is recovered from the vessel by conventional distillation
  7. customThe cyclohexanone used in the preparation of epsilon caprolactone

Sources & evidence

ORD record
ord-0435ef83d5aa450b918735bf2b184f23
Source dataset
uspto-grants-1977_11
Patent number
US04057537

Reaction notes

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