Sulfuric Acid → Phenol

HRID 2306347Notes

Reaction equation

HRID 2306347 reaction equation
[O-:1]O.[C:3]1([CH:9]([CH3:11])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.S(=O)(=O)(O)[OH:13]>>[C:3]1([OH:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:3]1([CH:9]([CH3:11])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:11][C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[CH2:10].[C:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:1])[CH3:11]

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 53627471Cumen hydroperoxide

Product 4

HCID 996PhenolHCID 7406CumeneHCID 7407Alpha-MethylstyreneHCID 7410Acetophenone

Procedure

On the industrial scale, the cumene hydroperoxide is usually treated with dilute sulphuric acid (5 to 25 percent concentration) at a temperature of about 50° C. to 70° C. After the cleavage is complete, the reaction mixture is separated and the oil layer distilled to obtain phenol and acetone together with cumene, alpha-methylstyrene, acetophenone and tars. The cumene may be recycled for conversion to the hydroperoxide and subsequent cleavage. The phenol produced in this way is suitable for use in resins although further purification is required for pharmaceutical grade product.

Workup

  1. customthe reaction mixture is separated
  2. distillationthe oil layer distilled

Sources & evidence

ORD record
ord-39b483c745c246a1b2b01d25395de21e
Source dataset
uspto-grants-2002_08
Patent number
US06441251B1

Reaction notes

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