6-Amino-1-hexanol → N-(6-hydroxyhexyl)octadecyl succinimide

HRID 1253397Notes

Reaction equation

HRID 1253397 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].[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33]>>[OH:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][N:26]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 199606-Amino-1-hexanolHCID 965622,5-Furandione, dihydro-3-octadecyl-

Product 1

HCID 68773496N-(6-hydroxyhexyl)octadecyl succinimideYield 69%

Procedure

A 300 mL reaction flask was charged with 63.2 g of octadecyl succinic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 21.0 g of 6-amino-1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and the resulting mixture was reacted at 160° C. for 3.5 hours under continuous nitrogen purging and with vigorous stirring. The reaction product was purified by silica gel column chromatography, yielding 55.87 g of N-(6-hydroxyhexyl)octadecyl succinimide (yield: 69.0%).

Workup

  1. customA 300 mL reaction flask
  2. customthe resulting mixture was reacted at 160° C. for 3.5 hours under continuous nitrogen purging and with vigorous stirring
  3. customThe reaction product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8d8ab1f5205547cea782269ae335cb2e
Source dataset
uspto-grants-2013_06
Patent number
US08455413B2

Reaction notes

Loading…