DE615399C - Process for the preparation of alkyl acetamides - Google Patents
Process for the preparation of alkyl acetamidesInfo
- Publication number
- DE615399C DE615399C DESCH96723D DESC096723D DE615399C DE 615399 C DE615399 C DE 615399C DE SCH96723 D DESCH96723 D DE SCH96723D DE SC096723 D DESC096723 D DE SC096723D DE 615399 C DE615399 C DE 615399C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- parts
- hydrogen
- acetamides
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Darstellung von Alkylacetamiden Bei der Herstellung von Alhylacetamiden nach bekannten Verfahren werden nur mangelhafte Ausbeuten erzielt.Process for the preparation of alkylacetamides During manufacture of Alhylacetamiden by known processes only poor yields are achieved.
Es wurde nun gefunden, daß man derartige gesättigte Acetamide sehr bequem -und mit guten Ausbeuten dadurch herstellen kann, daß man von den leicht herstellbaren ungesättigten Acetamiden ausgeht -und diese der katalytischen Hydrierung bei Temperaturen von nicht über i oo° unterwirft. Diese glatte Überführung der ungesättigten Acietamide in gesättigte ist als überraschend zu bezeichnen, da bekannt ist, daß Acetamid bei der Behandlung mit gewissen Reduktionsmitteln seinen Säureamidcharakter verlieren kann (vgl. B e i 1 s t e i n, Handb-. @d. organ. Chemie, q.. Aufl., Bd. 2, S. 176, Abs. 2, Zeilen 9 bis 14).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).
Die Überführung ungesättigter Alkylgruppen in gesättigte in Gegenwart von Wasserstoff und Platinmohr oder Palladium ist bekannt (vgl. H o 11 e m a n , Lehrb. d. organ. Chemie, i i. Aufl., 1913, S. 12q.). Es handelt sich dort jedoch um die Reduktion von Doppelbindungen in reinem Kohlenwasserstoff, während das vorliegende - Verfahren die Absättigung von Doppelbindungen in substituierten Verbindungen betrifft. Beispiel i 15 Teile Diallylmethylacetamid, in 150 Teilen Alkohol gelöst, werden mit 2 g eines wie üblich hergestellten Nickelkatalysators im Autoklaven bei 5o° bis iooAtm. Druck mit Wasserstoff behandelt. Sobald die Wasserstoffaufnahme zum Stillstand gekommen ist, wird die alkoholische Lösung filtriert und der Alkohol abdestilliert. Nach Umkristallisieren aus Benzin hinterbleibt das Dipropylmethylacetamid als farblose kristalline Massre vom Schmelzpunkt 33' und Siedepunkt s,nm. 180°.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 °.
Beispiele 18 Teile Triallylacetamid in 9o Teilen Alkohol werden mit i Teil Palla.diumkatalysator versetzt und bei Zimmertemperatur mit Wasserstoff behandelt. Sobald die Wasserstoffaufnahme zum Stillstand gekommen ist, wird vom Katalysator abfiltriert und nach Abtreiben des Lösungsmittels im Vakuum destilliert. Siedepunkt 11"" 161", Schmelzpunkt 68 bis 69°. Die- Ausbeute ist annähernd quantitativ.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.
Beispiel 3 i 9 Teile Crotyldiallylacetamid, gelöst in 8o Teilen Alkohol, werden mit i Teil Palla.diumkatalysator versetzt und bei. Zimmertemperatur mit Wasserstoff behandelt. Sobald die Wasserstoffaufnahme zum Stillstand gekommen ist, wird vom Katalysator abfiltriert und das Lösungsmittel abdestilliert. Es hinterbleibt das Dipropylbutylacetamid in quantitativer Ausbeute. Durch Umkristallisieren aus @ Benzin erhält man es als schneeweiße Kristalle vom Schmelzpunkt 63 bis 6q.°. Beispiel q.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 Teile Decylenacetamid (UndecyIensäureamid) in 15o Teilen Alkohol werden mit i Teil Bariumsulfatpalladiumkatalysator versetzt und bei Zimmertemperatur mit Wasserstoff behandelt. Sobald die Wasserstoffaufnahme zum Stillstand gekommen, wird filtriert und das Lösungsmittel abdestilliert. Nach Reinigung erhält man. das Undecansäureamid vom Schmelzpunkt 1o3°.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)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESCH96723D DE615399C (en) | 1932-02-03 | 1932-02-03 | Process for the preparation of alkyl acetamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DESCH96723D DE615399C (en) | 1932-02-03 | 1932-02-03 | Process for the preparation of alkyl acetamides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE615399C true DE615399C (en) | 1935-07-03 |
Family
ID=7445941
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DESCH96723D Expired DE615399C (en) | 1932-02-03 | 1932-02-03 | Process for the preparation of alkyl acetamides |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE615399C (en) |
-
1932
- 1932-02-03 DE DESCH96723D patent/DE615399C/en not_active Expired
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