Abstract
The relative reactivities of the primary and secondary amino groups of diethylene triamine with fatty acids depend on the thermal reaction conditions. Without solvents, the primary amines are more reactive than the secondary amine for steric reasons, and the reaction results mainly in the 1,3-diamide. However, in dilute solution, the secondary amine shows higher reactivity than the primary amines, and the reaction proceeds probably by way of the 1,2-diamide, which forms imidazolines under much milder conditions than from the 1,3-diamide. The hydrolysis of imidazoline to the 1,2-diamide as the major product confirmed the higher reactivity of the secondary amine.
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Wu, Y., Herrington, P.R. Thermal reactions of fatty acids with diethylene triamine. J Amer Oil Chem Soc 74, 61–64 (1997). https://doi.org/10.1007/s11746-997-0120-2
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DOI: https://doi.org/10.1007/s11746-997-0120-2