Design and Synthesis of Novel N,N‘-Bis(1-carboxy-15-hydroxy-n-pentadec-8-yl)alkyl or -Aryl Diamides by Acid-Catalyzed Addition of Nitriles To Ambrettoleic Acid via Amido−Imidol Tautomerization:  An Approach for Their Biological Importance and Possible Industrial Utilization

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.