Adipic Acid → Cyclohexanol

HRID 1109627Notes

Reaction equation

HRID 1109627 reaction equation
[C:1]([OH:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][C:6](O)=O>C1C=CC=CC=1>[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=1.[CH:1]1([OH:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 196Adipic Acid

Product 2

HCID 7966CyclohexanolHCID 8079Cyclohexene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The preparation of adipic acid is also carried out commercially by the selective hydrogenation of benzene to form cyclohexene, separation of the cyclohexene from the unconverted benzene and the over-hydrogenated cyclohexane by extractive distillation, then hydration of cyclohexene to form cyclohexanol, and the nitric acid oxidation of the cyclohexanol to adipic acid. See for example Kagaku Kogaku (Chemical Technology), vol. 55, No. 5, pp 382-385 (1991); "Technology for Manufacturing Cyclohexanol using Cyclohexene Technique" by Shikazo Senoo and Koji Nakagawa.

Workup

  1. customto form
  2. customcyclohexene, separation of the cyclohexene from the unconverted benzene
  3. distillationthe over-hydrogenated cyclohexane by extractive distillation

Sources & evidence

ORD record
ord-097e421e87b349c9943a2b26eda9ccd7
Source dataset
uspto-grants-1994_06
Patent number
US05321155

Reaction notes

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