A novel technique for the preparation of secondary fatty amides

Abstract

A technique for the synthesis of monosubstituted fatty amides at low temperature and ambient pressure was developed. This method involved the condensation of an amine with a triacylglycerol. The primary amine (ethyl, n-butyl, n-hexyl and n-octyl were tested) acted as reagent and solvent for the fatty substrates. No additional o~ ganic solvent or catalyst was added. Tallow, vegetable oils and fish oil all served well as substrates, as did pure tripalmitin. The rate of amidation was dependent upon temperature and the ratio of fat to amine. In a series of experiments conducted with tallow and n-butylamine at a fatmmine molar ratio of 1:16, amidation could be carded out at 20°C, producing n-butyltallowamide in 83% yield in 24 hr. When the fatmmine molar ratio was reduced to 1:8, and the temperature raised to 45°C, the amide yield was 87.6% in 24 hr. When the reaction was carried out at the boiling point of n-butylamine {78°C) and at a fat: amine ratio of 1:8, the amide yield was 93.2% in 4 hr. The reaction progressed more rapidly with higher molecular weight amines. The identity and purity of the amides was assessed by thin-layer chromatography and confirmed by elemental analyses and infrared and C 1~ nuclear magnetic resonance spectroscopy.

Synthesis of Linoleoyl Ethanolamide

“…Therefore, the optimization of reaction conditions was necessary to reduce the formation of esteramine and increase the conversion of methyl linoleate in the further experiments. 1 …”

An Improved Method for Synthesis of N‐stearoyl and N‐palmitoylethanolamine

“…The amount of ethanolamine influenced the solubility of products, and it perhaps acted as a catalyst [3,24,31]. Using ethanolamine as a solvent was economical because this material is readily available and affordable ($50.4 per liter from the Sigma Chemical Company).…”

Influence of vacuum on kinetic of low quality rapeseed oil amidation by aminoethylethanolamine

“…Fatty amides are obtained under similar conditions but without vacuum application [7]. However, secondary amides of fatty acids can be obtained even under the temperature of 50-60 ºС as shown in [8]. For that purpose, high excess of amine is required, the molar ratio of tripalmitoyl glycerol:amine 1:10.…”