epsilon-CAPROLACTONE → Cyclohexanol cyclohexanone

HRID 1602611Notes

Reaction equation

HRID 1602611 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[C:9]1(=[O:16])O[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.OCCCCCC(O)=O>C1CCCCC1>[C:6]1(=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][CH2:1]1.[CH:9]1([OH:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 10401epsilon-CAPROLACTONEHCID 123741,6-HexanediolHCID 144906-Hydroxyhexanoic Acid

Product 1

HCID 22492587Cyclohexanol cyclohexanone

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

We have found that this object is achieved by a process for preparing 1,6-hexanediol and ε-caprolactone from a carboxylic acid mixture comprising adipic acid, 6-hydroxycaproic acid and small amounts of 1,4-cyclohexanediols which is obtained as a by-product in the oxidation of cyclohexane to cyclohexanone/cyclohexanol using oxygen or oxygen-containing gases and by water extraction of the reaction mixture, by esterifying and hydrogenating a substream to give hexanediol and cyclizing 6-hydroxycaproic esters to give caprolactone, wherein

Sources & evidence

ORD record
ord-13a032379c8c4dc093267a58f1e94088
Source dataset
uspto-grants-1999_11
Patent number
US05981769

Reaction notes

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