Sulfuric Acid → Phenol

HRID 2047956Notes

Reaction equation

HRID 2047956 reaction equation
[CH:1]1(C2C=CC=CC=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O-]O.[CH:15]1(C2C=CC=CC=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.S(=O)(=O)(O)[OH:28].C(=O)([O-])[O-:33].[Na+].[Na+]>>[C:1]1([OH:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1(=[O:33])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 13229CyclohexylbenzeneHCID 86589629Cyclohexylbenzene hydroperoxide

Product 2

HCID 996PhenolHCID 7967Cyclohexanone

Procedure

Cyclohexylbenzene oxidation products (including cyclohexylbenzene hydroperoxide, CHBHP) using NHPI as the first catalyst with varying CHBHP concentrations are used (without first concentrating the hydroperoxide) in this example. An amount of 5.0 milliliters of such feed was charged into a glass flask held at 58° C. Toward this feed was added 5000 ppm of sulfuric acid diluted in acetone in a semi-batch mode. Cleavage reaction occurred instantaneously as indicated by the reaction exotherm. An aliquot was taken after 10 min and sulfuric acid was neutralized using 10 wt % sodium carbonate solution. The sample was analyzed by GC and the results are listed in Table 4. High conversion of CHBHP and high yield to phenol and cyclohexanone were observed in all cases.

Workup

  1. concentrationwith varying CHBHP concentrations
  2. concentrationwithout first concentrating the hydroperoxide) in this example
  3. additionAn amount of 5.0 milliliters of such feed was charged into a glass flask
  4. customheld at 58° C
  5. additionwas added 5000 ppm of sulfuric acid
  6. additiondiluted in acetone in a semi-batch mode
  7. customCleavage reaction

Sources & evidence

ORD record
ord-a815b8d906c544d6b3f0efaeea2e329c
Source dataset
uspto-grants-2013_11
Patent number
US08592634B2

Reaction notes

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