Benzene → Cyclohexylbenzene

HRID 661713Notes

Reaction equation

HRID 661713 reaction equation
[H][H].[C]=O.[CH:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>[Pd]>[CH:5]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 13229Cyclohexylbenzene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In addition, U.S. Pat. No. 5,146,024 discloses that benzene can be reacted with hydrogen in the presence of carbon monoxide and a palladium-containing zeolite X or Y to produce cyclohexylbenzene, which can then be converted in high yield to phenol and cyclohexanone by autooxidation with subsequent acid treatment. The hydroalkylation reaction is carried out at a liquid hourly space velocity (LHSV) of the benzene feed of about 1 to about 100 hr−1, a total reaction pressure of about 345 to about 10,350 kPa, a molar ratio of H2 to benzene of about 0.1:1 to about 10:1, a molar ratio of carbon monoxide to H2 of about 0.01:1 to about 0.3:1, and a temperature of about 100 to about 250° C. Preferred operating conditions are said to include a LHSV of the benzene feed of about 5 to about 30 hr−1, a total reaction pressure of about 1,380 to about 4,830 kPa, a molar ratio of H2 to benzene of about 0.2:1 to about 1:1, a molar ratio of CO to H2 of about 0.02:1 to about 0.1:1, and a reaction temperature of about 140 to about 200° C.

Sources & evidence

ORD record
ord-9bfff245f58b4befb42cd2c12114a91e
Source dataset
uspto-grants-2011_12
Patent number
US08084648B2

Reaction notes

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