Propylene Oxide → Cumene

HRID 420174Notes

Reaction equation

HRID 420174 reaction equation
[O-]O.[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4].C=CC.C1OC1C.C(O)(C1C=CC=CC=1)(C)C>[Ti]>[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 8252PropyleneHCID 120532-Phenyl-2-propanolHCID 53627471Cumen hydroperoxide

Product 1

HCID 7406Cumene

Reagents, catalysts & solvents 1

HCID 23963TitaniumCatalyst

Procedure

The alkylbenzene hydroperoxide obtained in the present invention can be used as a starting material for producing an alkylene oxide. For example, isopropylbenzene hydroperoxide obtained is reacted with propylene in the presence of a titanium-containing catalyst to produce a mixture of propyleneoxide and cumyl alcohol. After the mixture is separated, the obtained cumyl alcohol is reacted with hydrogen in the presence of hydrogenolysis catalyst to produce isopropylbenzene, and the isopropylbenzene is recycled as a starting material for the oxidation process. Further, the cumyl alcohol is converted into α-methylstyrene in the presence of dehydration catalyst, the α-methylstyrene is reacted with hydrogen in the presence of hydrogenation catalyst to produce isopropylbenzene, and the isopropylbenzene can be recycled as a starting material for the oxidation process. As another example, ethylbenzene hydroperoxide obtained is reacted with propylene in the presence of a titanium- or molybdenum-containing catalyst to produce a mixture of propylene oxide and 1-phenylethylalcohol. After the mixture is separated, the obtained 1-phenylethylalcohol is dehydrated in the presence of a dehydration catalyst to produce styrene.

Workup

  1. additioncontaining catalyst
  2. customto produce
  3. customAfter the mixture is separated
  4. customthe obtained cumyl alcohol is reacted with hydrogen in the presence of hydrogenolysis catalyst

Sources & evidence

ORD record
ord-e33641f30cb845ac86e84165b0915fa5
Source dataset
uspto-grants-2012_01
Patent number
US08093433B2

Reaction notes

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