Acetone → Cyclohexadecanone

HRID 2242793Notes

Reaction equation

HRID 2242793 reaction equation
[C:1]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=O.[H][H]>[Pd].O>[C:1]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 5346348-Cyclohexadecen-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 75695Cyclohexadecanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

100 kg of 8-cyclohexadecenone (odoriferously good quality: GC ratio of (E) and (Z) isomers was 2.5:1), 45 kg of acetone and 100 g of palladium on activated charcoal (Pd content: 5 wt. %) with 40% water content were placed in a stirred autoclave equipped with a gassing stirrer. The reaction mixture was hydrogenated for 12 hours at 35° to 40° C. and at 15 bar hydrogen pressure and then filtered. After removing the acetone 99.2 kg of cyclohexadecanone were obtained (GC content of cyclohexadecanone: >98%). The product thereby obtained was of a good perfumery quality. The perfumery quality could be improved still further by recrystallisation from methanol.

Workup

  1. customequipped with a gassing stirrer
  2. filtrationfiltered
  3. customAfter removing the acetone 99.2 kg of cyclohexadecanone

Sources & evidence

ORD record
ord-e51a6272491c4bf9b9a7da1e890aa16d
Source dataset
uspto-grants-2010_03
Patent number
US07674765B2

Reaction notes

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