Adipic Acid → Cyclohexanol

HRID 1492738Notes

Reaction equation

HRID 1492738 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 species 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 species cyclohexane, by extractive distillation

Sources & evidence

ORD record
ord-00f238f86f1a4579b872411400523da6
Source dataset
uspto-grants-1994_12
Patent number
US05374767

Reaction notes

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