Maleic Anhydride → Octadecyl hydrogen maleate
Reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([OH:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>>[CH2:8]([O:26][C:4](=[O:5])/[CH:3]=[CH:2]\[C:1]([OH:6])=[O:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]Participants
Procedure
Into an autoclave, were charged 295 parts of maleic anhydride and 825 parts of stearyl alcohol. A mixture was reacted at 60° C. for 5 hours under sealed condition, to obtain maleic acid monostearyl ester, containing 1.5% unreacted maleic anhydride. After adding to the mixture, 11.2 parts of toluene, 275 parts of allyl chloride and 530 parts of tri-n-propyl amine, an atmosphere was substituted with nitrogen. The mixture was reacted at 80° C. for 8 hours, and cooled to a room temperature. The mixture was rinsed by 90 parts of 10% hydrochloric acid aqueous solution, followed by distillation of toluene, to obtain 1,200 parts of stearyl allyl maleate of 94.5% purity and of Gardner Color 9. A molar ratio of maleic anhydride:stearyl alcohol was 1:1.02, and maleic acid monostearyl ester:allyl chloride:tri-n-propyl amine was 1:1.19:1.23.
Workup
- customA mixture was reacted at 60° C. for 5 hours
- customunder sealed condition
Sources & evidence
- ORD record
- ord-302bc05f7a0042f797ca13789c70cdc1
- Source dataset
- uspto-grants-1996_06
- Patent number
- US05523465
Reaction notes
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