GB451444A - Improvements in the manufacture and production of n-vinyl compounds - Google Patents

Abstract

N-Vinyldiarylamines are manufactured by causing acetylene to act at elevated temperatures, e.g. 100--200 DEG C. or higher, on diarylamines in the presence of substances having a strongly alkaline reaction or of alkali metals, e.g. the oxides, hydroxides and alcoholates of the alkali metals, or metallic potassium, if desired together with tertiary heterocyclic bases, e.g. pyridine or quinoline. The reaction may be carried out in a pressure-tight vessel into which the acetylene, advantageously under increased pressure, is led, preferably in admixture with inert gases, e.g. nitrogen, methane or hydrogen, or in a tower, the operation being in stages or continuous. Diluents such as alcohols, e.g. methyl, ethyl or butyl alcohol, glycols, e.g. ethylene or diethylene glycol, or hydrocarbons, e.g. cyclohexane, benzene, toluene, tetrahydronaphthalene or decahydronaphthalene may be employed. The products may be hydrogenated to produce the corresponding aromatic or cycloaliphatic ethyl compounds, and may be polymerized by heating or by the action of polymerization catalysts. In examples: (1) a mixture of acetylene and nitrogen under pressure is passed into phenyl-a -naphthylamine containing potassium hydroxide and pyridine, producing N-vinylphenyl-a -naphthylamine; the corresponding b -naphthylamine derivative may be similarly prepared; (2) acetylene is similarly reacted with diphenylamine in the presence of metallic potassium or sodium, or potassium or sodium hydroxide, to yield N-vinyldiphenylamine; (3) acetylene is similarly reacted with p-tolyl-a -naphthylamine in the presence of potassium hydroxide, to produce N-vinyl-p-tolyl-a -naphthylamine; (4) a -a <1>dinaphthylamine similarly yields N-vinyl-a -a <1>-dinaphthylamine; (5) acetylene is reacted with diphenylamine in xylene in the presence of potassium hydroxide, yielding N-vinyldiphenylamine. Other diarylamines specified are: phenyl-p-tolylamine and N-phenyl-2-aminoanthracene.