Acetone → Alpha-Methylstyrene

HRID 1075662Notes

Reaction equation

HRID 1075662 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]([CH3:11])=[O:10]>>[CH3:11][C:9]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:8].[CH3:8][C:9]([OH:10])([CH3:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 180AcetoneHCID 996Phenol

Product 2

HCID 7407Alpha-MethylstyreneHCID 120532-Phenyl-2-propanol

Procedure

Substantial quantities of α-methyl styrene (AMS) are produced as a byproduct in the cumene-phenol peroxidation process. Purified cumene is oxidized to form cumene hydroperoxide (CHP) which is then cleaved to phenol and acetone. A small amount of AMS is produced as a byproduct from the decomposition of dimethylbenzyl alcohol which is also formed with CHP in the oxidation step. The AMS can either be recovered as a byproduct or hydrogenated to cumene and recycled to the phenol process. Since the market for AMS is limited, hydrogenation to cumene is the usual option. The typical composition of the cumene/AMS stream is 5 to 80% AMS with trace amounts of methyl benzofuran, mesityl oxide and acetophenone.

Sources & evidence

ORD record
ord-fd2308ff7a26432f8e99e33ce0924bcf
Source dataset
uspto-grants-1999_05
Patent number
US05905178

Reaction notes

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