Ethanolamine → N-(2-hydroxyethyl)octadecyl succinimide

HRID 1253395Notes

Reaction equation

HRID 1253395 reaction equation
[CH2:1]([CH:19]1[CH2:24][C:23](=[O:25])[O:22][C:20]1=O)[CH2:2][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].[CH2:26]([CH2:28][NH2:29])[OH:27]>>[OH:27][CH2:26][CH2:28][N:29]1[C:23](=[O:25])[CH2:24][CH:19]([CH2:1][CH2:2][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])[C:20]1=[O:22]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 965622,5-Furandione, dihydro-3-octadecyl-

Product 1

HCID 68772964N-(2-hydroxyethyl)octadecyl succinimideYield 54%

Procedure

A 50 mL reaction flask was charged with 17.6 g of octadecyl succinic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 3.1 g of ethanolamine (manufactured by Tokyo Chemical Industry Co., Ltd.), and the resulting mixture was reacted at 160° C. for 4 hours under continuous nitrogen purging and with vigorous stirring. The reaction product was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane), yielding 10.6 g of N-(2-hydroxyethyl)octadecyl succinimide (yield: 54%).

Workup

  1. customA 50 mL reaction flask
  2. customthe resulting mixture was reacted at 160° C. for 4 hours under continuous nitrogen purging and with vigorous stirring
  3. customThe reaction product was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ccdf626f74a94cbf81036393225a60c5
Source dataset
uspto-grants-2013_06
Patent number
US08455413B2

Reaction notes

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