Phenol → Cumene

HRID 2198595Notes

Reaction equation

HRID 2198595 reaction equation
C1([OH:7])C=CC=CC=1.[C:8]1([CH:14]([CH3:16])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O-]O.[C:19]1([CH:25]([CH3:27])[CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[C:8]1([CH:14]([CH3:16])[CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:26][C:25]([CH3:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:7].[C:14]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])[CH3:16]

Participants

7

Reactant 3

HCID 996Phenol3×HCID 7406Cumene2×HCID 53627471Cumen hydroperoxide5×

Product 3

HCID 7406CumeneHCID 7410AcetophenoneHCID 120532-Phenyl-2-propanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Phenol is manufactured via air oxidation of cumene to cumene hydroperoxide (CHP), followed by acid-catalyzed cleavage of the latter to phenol and acetone. CHP decomposition is a very exothermic reaction which is normally carried out on a commercial scale in continuous stirred or back-mixed reactors. In such reactors only a small fraction of CHP is unreacted any given time and the reaction medium consists essentially of the products of decomposition of CHP, i.e., phenol and acetone, plus any solvent (e.g., cumene) and other materials added with CHP to the reactor. During cumene oxidation small amounts of dimethyl phenyl carbinol (DMPC) and acetophenone are also formed. In the presence of acid catalyst, DMPC dehydrates to alpha-methylstyrene (AMS), a useful by-product. Very high yields of AMS can be obtained from pure DMPC, e.g., 98% yield upon dehydration over acidic silica at 300° C. In the presence of phenol, however, and more specifically in phenol/acetone/cumene which is solvent in decomposition of technical CHP/DMPC mixtures, the ultimate AMS yield is normally about 50-60 mol% of the DMPC. Main by-products are AMS dimers and cumylphenol which have no commercial value. Formation of cumylphenol also reduces the phenol yield.

Workup

  1. customa very exothermic reaction which
  2. additionback-mixed reactors

Sources & evidence

ORD record
ord-a5a70fcb15e249268c37a336ecd2c8ba
Source dataset
uspto-grants-1982_11
Patent number
US04358618

Reaction notes

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