Palmitic Acid → Palmitic anhydride

HRID 260134

Reaction equation

HRID 260134 reaction equation
[C:1]([OH:18])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(O[C:23](=[O:25])[CH3:24])(=O)C>C1CCCCC1>[C:1]([O:18][C:23](=[O:25])[CH2:24][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][CH3:1])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 985Palmitic Acid2×HCID 7918Acetic Anhydride

Product 1

HCID 69339Palmitic anhydride

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Palmitic acid (512.04 g, 2.00 moles) and acetic anhydride (204.05 g, 2.00 moles) were charged to a two liter reaction flask fitted with an overhead stirrer, thermometer, condenser and nitrogen inlet. The mixture was heated gently with stirring to allow the solid palmitic acid to melt (61° C. to 64° C.). Heating was continued until the reflux temperature had been reached (147° C.), this temperature was maintained for a period of one hour. The resultant mixture was cooled to room temperature to allow a light yellow solid to form, this was slurried in cyclohexane (100 ml), filtered and recrystallised from petroleum ether 60-80. The recrystallised wet solid was placed in a vacuum oven at 40° C. until dry of residual acetic acid. The resultant white powdery solid was stored under vacuum in the presence of silica gel. The yield of palmitic anhydride was 458.49 g which represented a 92.8% chemical yield.

Workup

  1. customfitted with an overhead stirrer
  2. temperatureThe mixture was heated gently
  3. custom(61° C. to 64° C.)
  4. temperatureHeating
  5. custom(147° C.)
  6. temperaturethis temperature was maintained for a period of one hour
  7. customto form
  8. filtrationfiltered
  9. customrecrystallised from petroleum ether 60-80
  10. customwas placed in a vacuum oven at 40° C.
  11. dry with materialuntil dry of residual acetic acid

Sources & evidence

ORD record
ord-dfd6bab83436493486bd1a795b68e9ad
Source dataset
uspto-grants-1996_06
Patent number
US05525709

Linked notes

Loading…