DE636213C - Process for the production of N-vinyl compounds - Google Patents

Description

Process for the preparation of N-vinyl compounds Subject matter of the patent 61S i2o is a process for the production of N-vinyl compounds, according to which one acetylene in the presence of basic substances on pyrrole or the pyrrole ring containing organic compounds can act at elevated temperature.

It has now been found that industrially versatile N-vinyl compounds are also obtained if acetylene is converted to compounds of the formula in the presence of basic substances at elevated temperature can act, in the R and R, the same or different aryl groups. The aryl groups can also contain any desired carbon residues, e.g. ß. Methyl, ethyl or plienyl groups.

The implementation conditions are generally those in the main patent b. described in consideration. Of substances with an alkaline effect, which include for the present Implementation are suitable, include the oxides and hydroxides of the alkali metals the alkali metals themselves, especially called metallic potassium.

Through the addition of hydrogen, the new N-vinyl compounds converted into the corresponding aromatic or cycloaliphatic ethyl compounds will. They can be polymerized by heat or under the influence of catalysts.

The compounds obtainable by the present process can used with advantage for the production of plastics, dyes and medicines "verden.

EXAMPLE 1 A mixture of 100 parts of phenyl-naphthylamine and 3 parts of potassium hydroxide is shaken in a shake bomb at 10 ° to 90 ° and below 15 to 25 atm. Pressure treated with acetylene diluted with nitrogen in a ratio of 2: 1 until 12 parts of acetylene are absorbed, which is the case after about 3 hours. This gives a brown syrup which can be distilled at 1 mm pressure (bp 168 to 1 70 '). The one with it . The liquid obtained crystallizes after a while. After dissolving from ammonia-containing ethanol one obtains: s pure vinylphenyl-cc-naphthylamine; it melts at 8o to 83 °.

Vinylphenyl-13-liaphthylamine can be obtained in a similar manner that boils under i mm pressure at 165 ° and. melts at 79 to 82 °. example 2 Acetylene, diluted with nitrogen in the ratio 2: r, is left in the above Way to a mixture of 100 parts diphenylamine and 1 part metallic potassium act; about 115 parts of acetylene are taken up over the course of 3 hours. Man thus receives the vinyldiphenylamine in the form of a brown crystal mass, which is produced by distillation under reduced pressure (boiling point 89 to ro8 °) or dissolving from ethanol in the presence can be cleaned of some alkali. Colorless leaflets are obtained in this way Melting 52 to 54 °. The compound is easily decomposed. It colors itself when Standing in air with partial liquefaction brown, while with increased Temperature is colored deep red by oxygen: Instead of i part metallic Potassium, 2 to 3 tons of potassium hydroxide can be used. Also sodium or sodium hydroxide are suitable, but in this case the acetylene uptake is less smooth. Example 3. 12 parts of acetylene are used to prepare #linyl-p-tolyl-u-naphthylamine to t oo parts of p-tolyl-a-naphthylamili in the presence of 3 parts of potassium hydroxide conditions similar to those described in the previous examples, attached. The `new compound boils at 161 'under 1 mm of pressure and crystallizes when standing longer. It melts after recrystallization from ammonia-containing Methanul at 72 to 78 °.

Example 4 An i oo parts a. a'-Dinaphthylamine are albgelosed with the addition of 3 parts of potassium hydroxide at 19o ° ro parts of acetylene, vinyl-a. af-dinäphthylamin arises in the form of a brown mass. Example 5 Acetylene is allowed to act in the manner described above on a mixture of 50 parts of diphenylamine, 50 parts of xylene and II / 2 parts of potassium hydroxide. The amount of acetylene required to form the vinyl compound is absorbed after about 7 hours. The solvent is then distilled off from the brown liquid. The residue consists of vinyldiplienylamine, which can be purified in the usual way.

Claims (1)

PATENT CLAIM: Process for the production of N-vinyl compounds, through this. characterized in that acetylene is used in the presence of basic substances lets act on diarylamines at elevated temperature.