Abstract
The synthesis of a water soluble azo initiators from 2,2’-azodiisobutyronitrile (AIBN) was performed in three steps: reaction of dinitrile with aromatic alcohols in the presence of HCl to form bisiminoesters hydrochlorides which are hydrolyzed to the esters and final regioselective sulfonation of the aromatic esters. The thermal decomposition of the azo initiators obtained leads to formation of two surface active radicals which can start the chain reaction.
Highlights
One of the domains of free radical chemistry is industrial polymerization of alkenes
The synthesis of a water soluble azo initiators from 2,2’-azodiisobutyronitrile (AIBN) was performed in three steps: reaction of dinitrile with aromatic alcohols in the presence of HCl to form bisiminoesters hydrochlorides which are hydrolyzed to the esters and final regioselective sulfonation of the aromatic esters
The thermal decomposition of the azo initiators obtained leads to formation of two surface active radicals which can start the chain reaction
Summary
One of the domains of free radical chemistry is industrial polymerization of alkenes. The most appropriate reaction seems to be the Pinner synthesis [3,4] consisting in reaction of the starting nitrile with excess anhydrous alcohol and hydrogen chloride to give the respective iminoester hydrochloride. The latter can be subsequently hydrolyzed to ester. The ester, which contains a benzene ring, can be sulfonated in an anhydrous medium (Scheme 1) Another possible modification of the nitrile group consists in its transformation into an amide group via a Ritter reaction [5]
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