We have previously reported the preparation of higher
tert-amin from fatty ester and
tert-amine. This report deals the preparation of unsaturated higher amine by similar method from unsaturated fatty ester.
Ethyl oleate and triethylamine were reacted at the condition of hydrogenolysis, obtaining unsaturated higher
tert-amine, Hydrogenolysis of unsaturated fatty ester Cu-Cr-O catalyst gives saturated alcohol, but in the presence of amine, C-C double bond maintained about 50%. And the presence of Cd salt as a co-catalyst increased the survival of unsaturation of the product up to 60% approx.
The reaction condition that gave the best yield of 86% for the
tert-amine was as follows.
Mole ratio of ethyloleate ; triethylamine=1 : 5
Weight % of the catalyst to sample ester : 20%
Cadmium acetate wt% to sample ester : 4%
Initial hydrogen pressure : 100kg/cm
2Reaction temperature : 300°C
Reaction time : 3hr
In the case sperm oil, a good result was obtained in 80% yield of unsaturated amine with approx. 90% of survival unsaturation under higher initial pressure, 150kg/cm.
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