Nitrogen → Cyclohexanone

HRID 1744426Notes

Reaction equation

HRID 1744426 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:7]N1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2C1=O.[O:19]=O.N#N>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.CC(CC(C)=O)=O.CC(CC(C)=O)=O.CC(CC(C)=O)=O.[Co].C(O)(=O)C>[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:10]1([OH:19])[CH2:11][CH2:14][CH2:15][CH2:16][CH2:17]1.[C:12]([O:13][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:19])[CH3:11]

Participants

10

Reactant 4

HCID 947NitrogenHCID 977OxygenHCID 8078CyclohexaneHCID 10665N-Hydroxyphthalimide

Product 3

HCID 7966CyclohexanolYield 33%HCID 7967CyclohexanoneYield 57.8%HCID 12146Cyclohexyl acetateYield 9.3%

Reagents, catalysts & solvents 3

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 407384Cobalt(3+) acetylacetonateCatalystHCID 176Acetic AcidSolvent

Procedure

In a 316 stainless steel reactor having an internal volume of 300 ml, 10 g (118 mmol) of cyclohexane, 40 g of acetic acid, 38.8 mg (0.237 mmol) of N-hydroxyphthalimide, 29.6 mg (0.118 mmol) of cobalt(II) acetate tetrahydrate, and 42.4 mg (0.118 mmol) of tris(acetylacetonato) cobalt(III) were placed, and the reactor was sealed and was pressurized to 50 Kg/cm2 (4.9 MPa) with a gaseous mixture comprising 50% of O2 and 50% of N2. The liquid temperature was raised on an oil bath and was held at 110° C. Immediately after the liquid temperature reached 110° C., absorption of the gas began. The reaction was terminated by cooling 60 minutes later. A reaction mixture was analyzed to find that a conversion from cyclohexane was 1.8% and adipic acid was not produced. In addition, cyclohexanone (selectivity: 57.8%), cyclohexanol (selectivity: 33.0%), and cyclohexyl acetate (selectivity: 9.3%) were produced.

Workup

  1. customthe reactor was sealed
  2. temperatureThe liquid temperature was raised on an oil bath
  3. customwas held at 110° C
  4. customreached 110° C.
  5. customabsorption of the gas
  6. customThe reaction was terminated
  7. temperatureby cooling 60 minutes later
  8. customwas not produced

Sources & evidence

ORD record
ord-9b2e1d9e843a4df8b3c01d3ff760d2b8
Source dataset
uspto-grants-2006_03
Patent number
US07015356B2

Reaction notes

Loading…