Nitrogen → Cyclohexanone

HRID 1744428Notes

Reaction equation

HRID 1744428 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>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

8

Reactant 4

HCID 947NitrogenHCID 977OxygenHCID 8078CyclohexaneHCID 10665N-Hydroxyphthalimide

Product 3

HCID 7966CyclohexanolYield 46.1%HCID 7967CyclohexanoneYield 53.4%HCID 12146Cyclohexyl acetateYield 0.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 316 stainless steel reactor having an internal volume of 300 ml, 26 g (309 mmol) of cyclohexane, 14 g of acetic acid, and 100.8 mg (0.617 mmol) of N-hydroxyphthalimide 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 diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclohexane was 0.23% and adipic acid was not produced. In addition, cyclohexanone (selectivity: 53.4%), cyclohexanol (selectivity: 46.1%), and cyclohexyl acetate (selectivity: 0.5%) 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. additionA reaction mixture was diluted with 60 g of acetic acid
  9. dissolutionto thereby dissolve all of solid matters
  10. customwas not produced

Sources & evidence

ORD record
ord-055f398350984acd84b8ac5e9b6e4c92
Source dataset
uspto-grants-2006_03
Patent number
US07015356B2

Reaction notes

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