Cyclohexane → Adipic Acid

HRID 2221433Notes

Reaction equation

HRID 2221433 reaction equation
[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O:19][C:20]([C:22]1[CH:23]=[C:24]2[C:29](=[O:30])N(O)[C:26](=[O:27])[C:25]2=[CH:32][CH:33]=1)=[O:21])CCCCCCCCCCC.[N+]([O-])=[O:35]>C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[CH:1]1([OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:22]1(=[O:35])[CH2:23][CH2:24][CH2:25][CH2:32][CH2:33]1.[C:20]([OH:19])(=[O:21])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:27])=[O:35].[C:20]([OH:19])(=[O:21])[CH2:22][CH2:23][CH2:24][C:29]([OH:30])=[O:35]

Participants

8

Reactant 3

HCID 8078CyclohexaneHCID 109157654-dodecyloxycarbonyl-N-hydroxyphthalimideHCID 178526396Nitrogen Dioxide

Product 4

HCID 196Adipic AcidHCID 743Glutaric AcidHCID 7966CyclohexanolHCID 7967Cyclohexanone

Reagents, catalysts & solvents 1

HCID 12525Manganous AcetateCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 4 ml (37 mmol) of cyclohexane, 0.1 mmol of 4-dodecyloxycarbonyl-N-hydroxyphthalimide, 0.01 mmol of acetylacetonatocobalt(II), 0.001 mmol of manganese(II) acetate and 0.06 mmol of nitrogen dioxide was stirred at 80° C. in an atmosphere of air (10 atm=1 MPa) for 2 hours and thereby yielded 0.30 mmol of cyclohexyl alcohol, 0.65 mmol of cyclohexanone, 0.10 mmol of adipic acid and 0.09 mmol of glutaric acid. The total amount of the four products was 1.14 mmol, and the amount of K/A oil was 0.95 mmol.

Sources & evidence

ORD record
ord-d691032f2b5d440a966786992c2a17b8
Source dataset
uspto-grants-2008_05
Patent number
US07368615B2

Reaction notes

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