Water → 2-Octadecenyl succinic acid
Reaktionsgleichung
[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]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
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.