Reactions of fatty acids with amines. Part 2. Sequential thermal reactions of stearic (octadecanoic) acid with some 1,2- and 1,3-aminoalcohols and bis-amines

Abstract

Thermal reactions of stearic (octadecanoic) acid with 2-aminoethanol and 3-aminopropanol in a heavy hydrocarbon oil as solvent involved (i) salt formation, (ii) stearoylation of the amino-nitrogen, and (iii) a stearoyl transfer between two molecules of the stearamidoalcohol to give the amido-ester. Each successive step took place at a higher temperature. The reaction of the stearamidoalcohols with thionyl chloride involved N ⇌ O stearoyl rearrangements, and did not yield stable cyclised products. Thermal reactions of stearic acid with some propane-1,3-diamine and with bis-(2-hydroxyethyl)amine gave diamides and amidoesters.