Interest in the biological and industrial potential of oleochemicals has resulted in the development of various synthetic procedures for the introduction of heteroatoms into the fatty acid
chain. Thus, several novel N,N‘-bis(1-carboxy-15-hydroxy-n-pentadec-8-yl)alkyl or -aryl diamides have been synthesized by the reaction of different nitriles with ambrettoleic acid. The
specific nitriles malononitrile, succinonitrile, glutaronitrile, adiponitrile, pimelonitrile, suberonitrile azelanitrile, and 1,2-dicyanobenzene were added to the double bond of ambrettoleic acid
in the presence of concentrated sulfuric acid, and the resulting species were then hydrolyzed.
The mechanism of acid-catalyzed addition of nitriles to ambrettoleic acid has been confirmed
by its amido−imidol tautomerization. These newly synthesized oleochemicals have been
studied and characterized by FTIR, 1H NMR, and 13C NMR spectroscopies; MS; and elemental
analysis.
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