Benzene → Cyclohexanol

HRID 2057792Notes

Reaction equation

HRID 2057792 reaction equation
[H][H].[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH-:11].[Na+].[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1CCCCC1>[CH:13]1([OH:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 86597010Potassium phosphate sodium hydroxideHCID 178418361HCID 178418361, compound2×HCID 178506046HCID 178506046, compound

Product 2

HCID 7966CyclohexanolHCID 8079Cyclohexene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

In a high pressure glass bomb (ca. 20 ml), 200 mg. of the catalyst prepared above, 2 ml. of benzene, and 5 ml. of 40% sulfuric acid were provided with a small bar magnet coated with polytetrafluoroethylene. After replacement with hydrogen, the bomb was heated at 100° C. under 10 Kg/cm2G pressure of hydrogen for 4 hours with magnetic stirring. After neutralization with about 13 ml. of aqueous alkali (ca. 40%K3PO4 -NaOH), the product was submitted to gas-liquid chromatography (column: 25%PEG-4000/C-22, 60-80 mesh, 3 m., 150° C., H2 20 ml./min). The chromatogram showed that the conversion of benzene was 1.39%, and the yields of cyclohexanol, cyclohexane, and cyclohexene were 0.42%, 0.77%, and 0.20%, respectively. The selectivity of cyclohexanol was 30%.

Workup

  1. customwas submitted to gas-liquid chromatography (column: 25%PEG-4000/C-22, 60-80 mesh, 3 m., 150° C., H2 20 ml./min)

Sources & evidence

ORD record
ord-e22c4d1cea9c40b0aff009a9c8f3d8af
Source dataset
uspto-grants-1980_07
Patent number
US04212990

Reaction notes

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