6-Hydroxyhexanoic Acid → epsilon-CAPROLACTONE

HRID 1602610

Reaction equation

HRID 1602610 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]>C1CCCCC1>[CH2:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1].[C:7]1(=[O:8])[O:9][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[C:7]1(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[CH:7]1([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 144906-Hydroxyhexanoic Acid

Product 3

HCID 10401epsilon-CAPROLACTONEHCID 123741,6-HexanediolHCID 22492587Cyclohexanol cyclohexanone

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

1,6-hexanediol and ε-caprolactone are prepared 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 by water extraction of the reaction mixture, by esterifying and hydrogenating a substream to give hexanediol and cyclizing 6-hydroxycaproic esters to give caprolactone.

Sources & evidence

ORD record
ord-93d42a08a91f4c059127dda534564591
Source dataset
uspto-grants-1999_11
Patent number
US05981769

Linked notes

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