Acetic Acid → Adipic Acid

HRID 1744005

Reaction equation

HRID 1744005 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4]CC1.[N+]([O-])(O)=O.[O:12]=O.[C:14]([OH:17])(=[O:16])[CH3:15]>[N+]([O-])([O-])=O.[Mn+2].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Co+2].[N+]([O-])([O-])=O>[C:1]([OH:7])(=[O:12])[CH2:6][CH2:5][CH2:4][CH2:15][C:14]([OH:17])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 944Nitric AcidHCID 977OxygenHCID 7967Cyclohexanone

Product 1

HCID 196Adipic Acid

Reagents, catalysts & solvents 2

HCID 25000Cobalt dinitrateCatalystHCID 61511Manganese nitrateCatalyst

Procedure

A solution containing 25 mmol of cyclohexanone, 0.5 mmol of manganese(II) nitrate, 0.5 mmol of cobalt(II) nitrate and 1.5 mmol of nitric acid in 25 ml of acetic acid was stirred for 5 h at 40° C. in an oxygen atmosphere under ambient pressure. Subsequently, the acetic acid was distilled off. The residue was found to consist mainly of adipic acid with some glutaric acid and a small amount of unreacted starting material. The conversion of cyclo-hexanone was found to be 97.5%, the selectivity of the oxidation to adipic acid being 93.4%.

Workup

  1. distillationSubsequently, the acetic acid was distilled off

Sources & evidence

ORD record
ord-ea8b88fa6ef14293914a9ca4eb3c2d0d
Source dataset
uspto-grants-2006_03
Patent number
US07012155B2

Linked notes

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