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Issue 4, 1978
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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

Richard N. Butler,  Cornelius B. O'Regan  and  Patrick Moynihan 

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.

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Article type: Paper
DOI: 10.1039/P19780000373
Citation: J. Chem. Soc., Perkin Trans. 1, 1978,0, 373-377
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    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

    R. N. Butler, C. B. O'Regan and P. Moynihan, J. Chem. Soc., Perkin Trans. 1, 1978, 0, 373
    DOI: 10.1039/P19780000373

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