Adipic Acid → 40677-77-8

HRID 1856114Notes

Reaction equation

HRID 1856114 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]([OH:29])(=O)[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26].[CH3:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].CS(O)(=O)=O>O>[C:25]([O:27][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:1]/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:29]

Participants

6

Reactant 4

HCID 196Adipic AcidHCID 6395Methanesulfonic AcidHCID 8900HeptaneHCID 5284499Oleyl Alcohol

Product 1

HCID 2083959140677-77-8

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Dioleyl adipate was synthesized by refluxing 733 grams (2.73 moles) oleyl alcohol, 190 grams (1.30 moles) adipic acid, 340 grams (500 ml.) heptane and 1.9 grams (0.02 mole) methane sulfonic acid under a nitrogen atmosphere for 5 hours, in a 3-liter, 3-necked flask equipped with an air driven stirrer, thermometer, reflux condenser and heating mantle. Approximately 47 ml. of water produced in the reaction was removed in a Dean-Stark trap. The reaction mixture was cooled to 25° C., diluted with 500 ml. of hexane and the resulting solution was washed 3 times with successive 200 ml. portions of 2% aqueous sodium hydroxide and water, followed by a water wash until the solution tested neutral using PH paper. The washed solution was clarified by vacuum filtration through a 1.4 inch bed of celite and dried over molecular sieves. Rotary evaporation removed most of the solvent from the reaction mixture. The remaining solvent was removed from the reaction mixture by high vacuum stripping at a pressure of 0.3 mm. Hg and a temperature of about 250° C. to about 265° C. The dioleyl adipate produced was examined and found to contain 2.1% oleyl alcohol.

Workup

  1. customDioleyl adipate was synthesized
  2. customin a 3-liter, 3-necked flask equipped with an air
  3. temperaturethermometer, reflux condenser
  4. temperatureheating mantle
  5. customwas removed in a Dean-Stark trap
  6. additiondiluted with 500 ml
  7. washof hexane and the resulting solution was washed 3 times with successive 200 ml
  8. washwash until the solution
  9. filtrationThe washed solution was clarified by vacuum filtration through a 1.4 inch bed of celite and
  10. customdried over molecular sieves
  11. customRotary evaporation
  12. customremoved most of the solvent from the reaction mixture
  13. customThe remaining solvent was removed from the reaction mixture by high vacuum stripping at a pressure of 0.3 mm. Hg
  14. customa temperature of about 250° C. to about 265° C

Sources & evidence

ORD record
ord-1b4d00c879f8405cbd1229e3cd45c0c2
Source dataset
uspto-grants-1980_08
Patent number
US04218331

Reaction notes

Loading…