Acetic Acid → Cyclohexanol

HRID 1744427Notes

Reaction equation

HRID 1744427 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=O.N#N.[C:11]([OH:14])(=[O:13])[CH3:12]>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:1]1(=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:11]1([OH:14])[CH2:12][CH2:3][CH2:2][CH2:1][CH2:6]1.[C:11]([O:14][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:13])[CH3:12]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 947NitrogenHCID 977OxygenHCID 8078Cyclohexane

Product 3

HCID 7966CyclohexanolYield 70.3%HCID 7967CyclohexanoneYield 28.2%HCID 12146Cyclohexyl acetateYield 1.5%

Reagents, catalysts & solvents 1

HCID 61372Cobalt(II) acetate tetrahydrateCatalyst

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, 179 mg (0.617 mmol) of bis(acetylacetonato)manganese(II) dihydrate, and 15.4 mg (0.0617 mmol) of cobalt(II) acetate tetrahydrate 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 0.11% and adipic acid was not produced. In addition, cyclohexanone (selectivity: 28.2%), cyclohexanol (selectivity: 70.3%), and cyclohexyl acetate (selectivity: 1.5%) 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-8ef503da2f5f426e81b729e65bcfc2fe
Source dataset
uspto-grants-2006_03
Patent number
US07015356B2

Reaction notes

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