15-cis-4,4'-Diapophytoene → Squalane

HRID 1184995Notes

Reaction equation

HRID 1184995 reaction equation
[CH3:1][C:2]([CH3:30])=[CH:3][CH2:4][CH2:5]/[C:6](/[CH3:29])=[CH:7]/[CH2:8][CH2:9]/[C:10](/[CH3:28])=[CH:11]/[CH:12]=[CH:13]\[CH:14]=[C:15](/[CH3:27])\[CH2:16][CH2:17]/[CH:18]=[C:19](\[CH3:26])/[CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24]>[Pd]>[CH3:25][CH:23]([CH2:22][CH2:21][CH2:20][CH:19]([CH2:18][CH2:17][CH2:16][CH:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][CH2:7][CH:6]([CH2:5][CH2:4][CH2:3][CH:2]([CH3:30])[CH3:1])[CH3:29])[CH3:28])[CH3:27])[CH3:26])[CH3:24]

Participants

3

Reactant 1

HCID 1401921915-cis-4,4'-Diapophytoene

Product 1

HCID 8089SqualaneYield 83.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
40 °C

Procedure

Dehydrosqualene prepared above was placed in a one liter Parr pressure reactor and 1.1 g of 5% Pd/C was added. The vessel was sealed and evacuated under house vacuum for twenty minutes (ca. 20 torr) and then pressurized with hydrogen gas up to 950 psi. The reaction is initially exothermic. After the initial exothermic stage of the reaction was complete the reaction temperature was maintained at 40° C. by external heating and later at 60° C. Hydrogen gas was added as needed to maintain the reaction rate. After 47 hours the reaction was judged complete by GCMS analysis so the crude reaction product was filtered through a silica gel pad 3 inches in diameter×3 inches high and the silica gel was washed with 550 mL 5% ethyl acetate in hexanes. After removal of the solvent by rotary evaporation the crude squalane weighed 332.6 g. The product was distilled in 3 batches using a Kugelrohr bulb to bulb apparatus to give 282.4 g squalane (83.4% yield over both steps).

Workup

  1. additionwas added
  2. customThe vessel was sealed
  3. customevacuated under house vacuum for twenty minutes (ca. 20 torr)
  4. temperatureby external heating and later at 60° C
  5. additionHydrogen gas was added
  6. temperatureto maintain the reaction rate
  7. customso the crude reaction product
  8. filtrationwas filtered through a silica gel pad 3 inches in diameter×3 inches high
  9. washthe silica gel was washed with 550 mL 5% ethyl acetate in hexanes
  10. customAfter removal of the solvent
  11. customby rotary evaporation the crude squalane
  12. distillationThe product was distilled in 3 batches

Sources & evidence

ORD record
ord-dd13d0f55157479a8e06f202ce1ba1af
Source dataset
uspto-grants-2014_03
Patent number
US08669403B2

Reaction notes

Loading…