Octanoic Acid → Pentaerythritol octanoate

HRID 1901310Notes

Reaction equation

HRID 1901310 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10]([OH:19])(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[PH2](O)=O>O>[C:10]([O:1][CH2:2][C:3]([CH2:8][O:9][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])([CH2:6][O:7][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:4][O:5][C:10](=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:19])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 379Octanoic AcidHCID 8285PentaerythritolHCID 4124402Phosphinic Acid

Product 1

HCID 76366Pentaerythritol octanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
190 °C

Procedure

879 g (0.87 moles) of the POE(20) pentaerythritol prepared in (a) above was charged to a flask for esterification having standard apparatus for agitation, heating and distillation. Agitation and a dry nitrogen sparge were started, and 551 g (3.8 moles) of caprylic acid (alkyl chain 98% minimum C8 acid value 388 mg KOH/g) and 0.8 g of hypophosphorous acid solution (50%) were added. The contents were heated to 180° C. with the removal of the water of esterification by distillation and held at 180°-190° C. until all water was removed. The hydroxyl number of the contents was checked, and the reaction was continued at 180°-190° C. until a maximum hydroxyl number of 5.0 mg KOH/g was reached, indicating greater than 99% conversion to the ester. A vacuum was pulled via the distillation system to 30 inches and the contents were stirred at 190° C. to remove the unreacted caprylic acid by distillation. The Acid value of the contents was checked, and the acid removal was continued at 180°-190° C. until a maximum acid value of 1.0 mg KOH/g was reached. The contents were then cooled to 70° C. and filtered to yield a compound of the formula

Workup

  1. additionabove was charged to a flask for esterification
  2. temperatureheating
  3. distillationdistillation
  4. customAgitation and a dry nitrogen sparge
  5. customwas removed
  6. customwas continued at 180°-190° C. until a maximum hydroxyl number of 5.0 mg KOH/g
  7. customto remove the unreacted caprylic acid
  8. distillationby distillation
  9. customthe acid removal
  10. customwas continued at 180°-190° C. until a maximum acid value of 1.0 mg KOH/g
  11. temperatureThe contents were then cooled to 70° C.
  12. filtrationfiltered
  13. customto yield a compound of the formula

Sources & evidence

ORD record
ord-a7e253f4183a4a3db475b24d6fd1cef9
Source dataset
uspto-grants-1996_11
Patent number
US05576470

Reaction notes

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