Phenol → Oxygen

HRID 724507Notes

Reaction equation

HRID 724507 reaction equation
[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-:10][OH:11].C1(C(C)C)C=CC=CC=1.C1(O)C=CC=CC=1.CC(C1C=CC=CC=1)=C>CC(C)=O>[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:10]=[O:11]

Participants

7

Reactant 4

HCID 996Phenol2×HCID 7406Cumene2×HCID 7407Alpha-MethylstyreneHCID 53627471Cumen hydroperoxide2×

Product 2

HCID 977OxygenHCID 7406Cumene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

It has been discovered that when a cumene oxidation product mixture containing cumene hydroperoxide (CHP) and DMPC is decomposed to produce phenol, acetone and alpha-methyl styrene by passing the cumene oxidation product mixture into a decomposing vessel containing indirect heat exchange surfaces wherein the cumene oxidation product mixture and an incoming circulating stream comprising cumene hydroperoxide, phenol, acetone and an acid catalyst are admixed, reacted and cooled by passage around the indirect heat exchange surfaces and then circulating a cooled stream comprising unreacted cumene hydroperoxide, phenol and acetone from the decomposing vessel to provide the circulating stream referred to hereinabove, an improved yield of alpha-methyl styrene is realized. A net reacted stream preferably comprising a cumene hydroperoxide concentration from about 0.5 to about 5 weight percent is removed from the circulating stream and recovered. The cumene oxidation product mixture is the result of cumene oxidation with oxygen and preferably comprises a cumene hydroperoxide concentration from about 60 to about 95 weight percent. The ratio of the flow rate of the cumene oxidation product mixture to the flow rate of the circulating stream is preferably from about 1:10 to about 1:100 in the decomposing vessel. In accordance with the present invention, a suitable and preferred acid catalyst is sulfuric acid.

Workup

  1. customreacted
  2. temperaturecooled by passage around the indirect heat exchange surfaces
  3. customto provide the circulating stream
  4. concentrationa cumene hydroperoxide concentration from about 0.5 to about 5 weight percent
  5. customis removed from the circulating stream
  6. customrecovered

Sources & evidence

ORD record
ord-2722978072b849c395b3688f9bb3b028
Source dataset
uspto-grants-2006_11
Patent number
US07141700B1

Reaction notes

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