Stearic Acid → N-(2-octadecanoyloxyethyl)-N-methyloctadecylamine

HRID 1602766Notes

Reaction equation

HRID 1602766 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:6][CH2:7][CH2:8][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][CH3:23])[CH3:5].[C:24](O)(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[C:24]([O:1][CH2:2][CH2:3][N:4]([CH2:6][CH2:7][CH2:8][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][CH3:23])[CH3:5])(=[O:42])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

3

Reactant 2

HCID 5281Stearic AcidHCID 13564486N-(2-hydroxyethyl)-N-methyl-octadecylamine

Product 1

HCID 19607499N-(2-octadecanoyloxyethyl)-N-methyloctadecylamineYield 96.5%

Conditions

Temperature
180 °C

Procedure

A four-neck flask provided with a stirrer, a thermometer and a dehydrating tube was charged with 200 g of the N-(2-hydroxyethyl)-N-methyloctadecylamine and 174 g of octadecanoic acid. The mixture was heated to 180° C. and maintained at this temperature for 12 hours while distilling off the water thus formed. Thus 350 g of N-(2-octadecanoyloxyethyl)-N-methyloctadecylamine was obtained. Based on the NMR and IR spectra, it was confirmed that this product had the following structure. This compound will be referred to as the enhancer 25 hereinafter. ##STR30##

Workup

  1. customA four-neck flask provided with a stirrer
  2. temperaturemaintained at this temperature for 12 hours
  3. distillationwhile distilling off the water
  4. customthus formed

Sources & evidence

ORD record
ord-b8fbae87be884f39b77c03e04dde29d6
Source dataset
uspto-grants-1999_11
Patent number
US05985794

Reaction notes

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