Maleic Anhydride → Dodecyl hydrogen maleate

HRID 259915Notes

Reaction equation

HRID 259915 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]>C1(C)C=CC=CC=1>[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

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 81931-Dodecanol

Product 1

HCID 5366034Dodecyl hydrogen maleate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into an autoclave, were charged 295 parts of maleic anhydride, 570 parts of lauryl alcohol and 85 parts of toluene. The mixture was reacted at 60° C. for 5 hours under sealed condition, to obtain maleic acid monolauryl ester, containing 0.2% unreacted maleic anhydride. After adding to the mixture, 5 parts of sodium hydroxide, 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 with 90 parts of 10% hydrochloric acid aqueous solution, followed by distillation of toluene under vacuum, to obtain 965 parts of lauryl allyl maleate of 98.6% purity and of Gardner Color 3. A molar ratio of maleic anhydride:lauryl alcohol was 1:1.02, and maleic acid monolauryl ester:allyl chloride:triethyl amine:formed water was 1:1.19:1.23:0.04.

Workup

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

Sources & evidence

ORD record
ord-afec3e37bbc542cb9baebc5e28be1898
Source dataset
uspto-grants-1996_06
Patent number
US05523465

Reaction notes

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