DE615399C - Process for the preparation of alkyl acetamides - Google Patents

Description

Process for the preparation of alkylacetamides During manufacture of Alhylacetamiden by known processes only poor yields are achieved.

It has now been found that such saturated acetamides can be found very easily can be produced conveniently - and with good yields - that one of the easily manufacturable unsaturated acetamides starts - and these the catalytic hydrogenation subjected at temperatures not exceeding i oo °. This smooth transfer of the unsaturated Acietamide in saturated is surprising because it is known that Acetamide retains its acid amide character when treated with certain reducing agents can lose (cf. B e i 1 s t e i n, Handb-. @d. organ. Chemistry, q .. ed., vol. 2, p. 176, para. 2, lines 9 to 14).

The conversion of unsaturated alkyl groups into saturated ones in the presence of hydrogen and platinum black or palladium is known (cf.H o 11 e m a n, Apprentice d. organ. Chemistry, i i. Ed., 1913, p. 12q.). It is there, however to the reduction of double bonds in pure hydrocarbon, while the present - Process relates to the saturation of double bonds in substituted compounds. Example i 15 parts of diallyl methylacetamide dissolved in 150 parts of alcohol are used with 2 g of a nickel catalyst prepared as usual in an autoclave at 50 ° until iooAtm. Pressure treated with hydrogen. As soon as the hydrogen uptake to the Has stopped, the alcoholic solution is filtered and the alcohol distilled off. After recrystallization from gasoline, the dipropylmethylacetamide remains as a colorless crystalline mass with a melting point of 33 'and a boiling point of 1.5 nm. 180 °.

Examples 18 parts of triallylacetamide in 90 parts of alcohol are mixed with i part of palladium catalyst is added and treated with hydrogen at room temperature. As soon as the hydrogen uptake has come to a standstill, the catalytic converter filtered off and, after driving off the solvent, distilled in vacuo. boiling point 11 "" 161 ", melting point 68 to 69 °. The yield is approximately quantitative.

Example 3 i 9 parts of crotyldiallylacetamide, dissolved in 80 parts of alcohol, are mixed with i part palladium catalyst and at. Room temperature with hydrogen treated. As soon as the hydrogen uptake has come to a standstill, the The catalyst is filtered off and the solvent is distilled off. It remains that Dipropylbutylacetamide in quantitative yield. By recrystallization from @ gasoline it is obtained as snow-white crystals with a melting point of 63 to 6q. °. Example q.

19 parts of decylene acetamide (undecylenic acid amide) in 150 parts of alcohol are mixed with i part of barium sulfate palladium catalyst and at room temperature treated with hydrogen. As soon as the hydrogen uptake has come to a standstill, is filtered and the solvent is distilled off. After cleaning, one obtains. the Undecanoic acid amide with a melting point of 10 °.

Claims (1)

PATENT CLAIM: Process for the preparation of alkylacetamides, characterized in that alkylene acetamides are subjected to the catalytic hydrogenation at temperatures not exceeding iöo °.