Acetic Acid → Acetate

HRID 2255523Notes

Reaction equation

HRID 2255523 reaction equation
C(O)C=C.[C:5]([O:8]C(=O)C)(=[O:7])[CH3:6].C(O)(=O)C.[C:16]([O:35]C)(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>>[C:5]([O-:8])(=[O:7])[CH3:6].[C:16]([O-:35])(=[O:34])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7858Allyl AlcoholHCID 7918Acetic AnhydrideHCID 5364509Methyl Oleate

Product 2

HCID 175AcetateHCID 5460221Oleic acid, ion(1-)

Procedure

Polyallyl acetate is prepared as described by Bartlett and Altschul, cited above. A 500-mL reaction flask equipped with a thermometer, stirrer, and reflux condenser is charged with 1.5 moles (102 mL) of allyl alcohol, 0.75 mole (71 mL) of acetic anhydride, and 1.5 moles (86 mL) acetic acid. Five mL concentrated sulfuric is added and the mixture heated under reflux for two hours. The mixture is poured slowly with stirring into ice water, and extracted with ice-cold sodium carbonate and cold saturated calcium chloride solutions. After drying with 12 g. of anhydrous potassium carbonate, the ester is distilled twice through an all-glass apparatus in a stream of nitrogen. The middle fractions only are collected to yield a product having a boiling point (124-126 mm) of 53.2° to 54° C. Using the method of Bartlett and Altschul, the polymer had an average of about 13 monomer units. The polymer is interesterified with methyl oleate as described in Example 1 above and purified to obtain polyallyl oleate.

Workup

  1. customA 500-mL reaction flask
  2. customequipped with a thermometer, stirrer
  3. temperaturereflux condenser
  4. concentrationFive mL concentrated sulfuric
  5. additionis added
  6. temperaturethe mixture heated
  7. temperatureunder reflux for two hours
  8. additionThe mixture is poured slowly
  9. extractionextracted with ice-cold sodium carbonate and cold saturated calcium chloride solutions
  10. customAfter drying with 12 g
  11. distillationof anhydrous potassium carbonate, the ester is distilled twice through an all-glass apparatus in a stream of nitrogen
  12. customThe middle fractions only are collected
  13. customto yield a product
  14. customa boiling point (124-126 mm) of 53.2° to 54° C
  15. custompurified

Sources & evidence

ORD record
ord-ce46d300f73f4e8d8babceac0ece38d9
Source dataset
uspto-grants-1993_08
Patent number
US05240996

Reaction notes

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