Ethanolamine → Oleoylethanolamide

HRID 654277Notes

Reaction equation

HRID 654277 reaction equation
CO[C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH2:22]([CH2:24][NH2:25])[OH:23]>CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-].[Ti+4]>[CH3:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]/[CH:12]=[CH:11]\[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([NH:25][CH2:24][CH2:22][OH:23])=[O:21]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 5364509Methyl Oleate

Product 1

HCID 5283454Oleoylethanolamide

Reagents, catalysts & solvents 1

HCID 21801Titanium tetrabutoxideCatalyst

Procedure

As in Example 1, 445.7 g (1.5 mol) of technical grade oleic acid methyl ester (sunflower oil fatty acid, oleic acid content approx. 85%, saponification value 188.8, iodine value 85), 184.2 g (3 mol) of ethanolamine and 5.1 g (0.015 mol, 1 mol-%) of titanium tetrabutylate were reacted under nitrogen and normal pressure at 140° to 150° C. to form oleic acid ethanolamide with removal of methanol by distillation. The excess ethanolamine was then distilled off at 4 hPa/120°-125° C. The temperature was then increased to 220°-265° C. at 0.08-0.1 hPa, the product and water distilling over. 2-(8-Heptadecen-1-yl)-2-oxazoline was obtained in a yield of 394.1 g (86% of the theoretical). n20 : 1.4700.

Sources & evidence

ORD record
ord-35495918eade408f8fdcb97bfcfc60d1
Source dataset
uspto-grants-1992_07
Patent number
US05130440

Reaction notes

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