A novel technique for the preparation of secondary fatty amides |
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Authors: | Alexander Bilyk Raymond G Bistline Jr George J Piazza Stephen H Feairheller Michael J Haas |
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Affiliation: | (1) ARS, Eastern Regional Research Center, U.S. Department of Agriculture, 600 East Mermaid Lane, 19118 Philadelphia, PA |
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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 andn-octyl were tested) acted as reagent and solvent for the fatty substrates. No additional organic 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 andn-butylamine at a fat:amine molar ratio of 1:16, amidation could be carried out at 20°C, producingn-butyltallowamide in 83% yield in 24 hr. When the fat:amine 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 ofn-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 C13 nuclear magnetic resonance spectroscopy. |
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Keywords: | Amidation amide cod liver oil corn oil cottonseed oil ethylamine n-butylamine n-butyl-hexadecanamide n-hexylamine n-octylamine soybean oil tallow triacylglycerol tripalmitin |
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