Maleic Anhydride → Dodecyl hydrogen maleate

HRID 259916Notes

Reaction equation

HRID 259916 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[CH2:8]([OH:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[CH2:8]([O:20][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][CH3:19]

Participants

3

Reactant 2

HCID 7923Maleic AnhydrideHCID 81931-Dodecanol

Product 1

HCID 5366034Dodecyl hydrogen maleate

Procedure

Into an autoclave, were charged 295 parts of maleic anhydride and 560 parts of lauryl alcohol. The mixture was reacted at 60° C. for 5 hours under sealed condition, to obtain maleic acid monolauryl ester, containing 1.3% unreacted maleic anhydride. After adding to the mixture, 275 parts of allyl chloride and 375 parts of triethyl 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, to obtain 960 parts of lauryl allyl maleate of 92.7% purity and of Gardner Color more than 10. A molar ratio of maleic anhydride:lauryl alcohol was 1:1, and maleic acid monolauryl ester:allyl chloride:triethyl amine was 1:1.19:1.23.

Workup

  1. customThe mixture was reacted at 60° C. for 5 hours
  2. customunder sealed condition

Sources & evidence

ORD record
ord-829fa0c54cc14acd9179c2c1622acaa0
Source dataset
uspto-grants-1996_06
Patent number
US05523465

Reaction notes

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