Among the extensive applications of oleochemicals as industrial products, nitrogen derivatives
of fatty acids such as amides have been extensively used as antislip and antiblock additives for
polythene films in which they are incorporated. They are also used as wall repellents for textiles
and as mold release agents, and they are employed in rubber goods and printing inks. Because
of this interest in the biological and industrial potential of oleochemicals, a series of novel N,N‘-bis(1-carboxy-15-hydroxy-n-pentadec-8-yl)alkyl or -aryl amides derivatives such as hydrazides,
thiosemicarbazides, oxadiazoles, and triazoles has been synthesized. These newly synthesized
oleochemicals have been studied and characterized by FTIR, 1H NMR, and 13C NMR spectroscopies and elemental analyses.
Celsia coromandeliana, Vahl Syn. Verbasum coromandelianum, (Vahl) Kuntze seed oil was found to contain 22.0% 9-hydroxyoctadec-cis-12-enoic acid (isoricinoleic acid) previously unknown in the Scrophulariaceae plant family. It also consists of other normal fatty acids such as lauric acid (1.3%), myristic acid (2.6%), palmitic acid (8.2%), stearic acid (3.2%), oleic acid (17.2%), and linoleic acid (45.5%). The identification and characterization were based on UV, FTIR, 1 H NMR, and mass spectra, GLC analysis, and chemical degradations.
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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