Water → 2-Octadecenyl succinic acid

HRID 444372Notes

Reaction equation

HRID 444372 reaction equation
[CH:1]([CH:19]1[CH2:24][C:23](=[O:25])[O:22][C:20]1=[O:21])=[CH: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][CH2:16][CH2:17][CH3:18].O.C(O)(=O)CCC(O)=[O:31]>>[CH:1]([CH:19]([CH2:24][C:23]([OH:22])=[O:25])[C:20]([OH:31])=[O:21])=[CH: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][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 962WaterHCID 1110Succinic AcidHCID 225771Dihydro-3-(1-octadecen-1-yl)-2,5-furandione

Product 1

HCID 2577252-Octadecenyl succinic acid

Conditions

Temperature
80 °C

Procedure

This is lactonized-2-octadecenyl succinic acid which is prepared as follows: A half mole (175 g) of 2-octadecenyl succinic anhydride and 0.55 mole (10 g) of water were mixed and heated in a reaction flask for a half hour at 80° C. Infrared analysis showed that complete conversion of the anhydride to succinic acid had occurred. While stirring at 80° C., 0.5 g of concentration sulfuric acid was added, and the reaction temperature was increased to 130°-140° C. Heating at 140° C. for 1.5 hours completely converted the di-carboxylic acid to the desired lactone acid products. When the cooled mixture was diluted with ether, a white solid separated from solution. Infrared analysis of the isolated solids revealed the presence of a 5-ring lactone acid (strong bands at 5.67 and 5.82 microns). Cooling the supernatant gave more solids. Further fractional crystallization of later crops afforded 6-ring lactone acid products. The combined weight of all crops revealed that the yield of lactone acid product was quantitative. A recrystallized sample of 5-ring lactone product melted at 112° C. and analyzed for 71.50% carbon, 10.77% H and 16.67% oxygen. Theory requires 71.49% C, 11.18% H, and 17.32% O.

Workup

  1. concentration0.5 g of concentration sulfuric acid
  2. additionwas added
  3. temperaturethe reaction temperature was increased to 130°-140° C
  4. temperatureHeating at 140° C. for 1.5 hours
  5. additionWhen the cooled mixture was diluted with ether
  6. customa white solid separated from solution
  7. temperatureCooling the supernatant
  8. customgave more solids
  9. customFurther fractional crystallization of later crops

Sources & evidence

ORD record
ord-d9d40216391341a297637a5e0c92b733
Source dataset
uspto-grants-1981_04
Patent number
US04264460

Reaction notes

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