Fatty Acid Amides. VI.² Preparation of Substituted Amidostearic Acids by Addition of Nitriles to Oleic Acid³

Fatty Acid-Based Radically Polymerizable Monomers: From Novel Poly(meth)acrylates to Cutting-Edge Properties

“…48 The first application of Ritter reaction to VO and their derivatives was firstly reported by Roe et al who grafted various nitrile compounds among which, acrylonitrile in the presence of sulfuric acid. 49 After 15 minutes at 30 °C, good yields were obtained for the amidostearic acids (< 90 %). The same procedure was used to functionalize other unsaturated FA with acrylonitrile such as erucic or erucastic acids.…”

“…These reactions are based on the Ritter reaction where the alkene is protonated in the presence of concentrated sulfuric acid to form a carbocation which can react with the nucleophilic nitrogen atom of the nitrile followed by hydrolysis to the corresponding amide . The first application of Ritter reaction to VOs and their derivatives was performed by using various nitrile compounds, among them acrylonitrile in the presence of sulfuric acid . After 15 min at 30 °C, good yields was obtained for the amidostearic acid (<90%).…”

Reactions of the Hydrocarbon Chain of Fatty Acids.

“…Conversion to the oxime and Beckmann rearrangement yielded a mixture Amidoundecanoic acids have been prepared by the interaction of 10-undecenoic acid or its ester with benzonitrile (221), acrylonitrile or methacrylonitrile (413), or hydrogen cyanide (455). Amidoóctadecanoic acids have been produced from oleic acid and the following nitriles: hydrogen cyanide (455), acetonitrile, propionitrile, acrylonitrile, benzonitrile, cyanoacetic acid, and succinonitrile (454). 12-Hydroxy-9(10)formamidoóctadecanoic acid was prepared from ricinoleic acid and hydrogen cyanide (455).…”

“…The introduction of a carboxyl group by the addition of carbon monoxide plus water to unsaturated fatty acids has been described recently (300, 454).…”

Chemistry of malononitrile

“…the double bond of oleic acid, in sulfuric acid, to give -cyanoacetamidostearic acid in 19 % yield 280. 1, in the presence of a metallic chloride, reacts with aromatic compounds, such as toluene, naphthalene, acenaphthene, aor /3-naphthol ether,1 -methylnaphthalene, and anthracene to give diketimides of type 193.…”