AT260936B - Verfahren zur Herstellung von neuen N-Vinyl-2-piperazinonen - Google Patents

Verfahren zur Herstellung von neuen N-Vinyl-2-piperazinonen

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Publication number
AT260936B
AT260936B AT180465A AT180465A AT260936B AT 260936 B AT260936 B AT 260936B AT 180465 A AT180465 A AT 180465A AT 180465 A AT180465 A AT 180465A AT 260936 B AT260936 B AT 260936B
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AT
Austria
Prior art keywords
carbon atoms
alkyl
hydrogen
substituted
membered saturated
Prior art date
Application number
AT180465A
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English (en)
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Rohm & Haas
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Publication of AT260936B publication Critical patent/AT260936B/de

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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    • C—CHEMISTRY; METALLURGY
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    • C—CHEMISTRY; METALLURGY
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    • C—CHEMISTRY; METALLURGY
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Description


   <Desc/Clms Page number 1> 
 



  Verfahren zur Herstellung von neuen   N-Vinyl-2-piperazinonen   
Die Erfindung bezieht sich auf ein Verfahren zur Herstellung von neuen N-Vinyl-2-piperazinonen. 



   Die nach dem erfindungsgemässen Verfahren herstellbaren N-Vinyl-2-piperazinone haben die allgemeine Formel 
 EMI1.1 
 worin R für Wasserstoff, Alkyl oder Cycloalkyl, mit bis zu 18 Kohlenstoffatomen, Aralkyl oder alkyl-   substituiertes Aralkyl mit bis zu 18 Kohlenstoffatomen, Dialkylaminoalkyl mit bis zu 12 Kohlenstoffatomen, wobei jede dieser Alkylgruppen bis zu 8 Kohlenstoffatome enthält oder Furfuryl steht, R2   Wasserstoff oder Methyl darstellt, R Wasserstoff, Alkyl oder Cycloalkyl, mit bis zu 18 Kohlenstoffatomen, Phenyl, Naphthyl und alkyl-, chlor-und alkoxysubstituiertes Phenyl oder Naphthyl, in welchem der Alkylanteil bis zu 18 Kohlenstoffatomen enthält, Aralkyl und alkylsubstituiertes Aralkyl mit bis zu 18 Kohlenstoffatomen oder 2-Furyl bedeutet,

     R Wasserstoff   oder Alkyl mit bis zu 4 Kohlenstoffatomen ist und R5 für Wasserstoff oder Alkyl mit bis zu 4 Kohlenstoffatomen steht, bzw.   R und R* zu-   sammen einschliesslich des Kohlenstoffatoms, an welches sie gebunden sind, einen 5-bis 7-gliedrigen gesättigten carbocyclischen Ring oder einen alkylsubstituierten 5-bis 7-gliedrigen gesättigten carbocyclischen Ring mit bis zu 18 Kohlenstoffatomen bilden können, bzw.   RundR   zusammen mit dem Kohlenstoffatom, an welches sie gebunden sind, einen 5-bis 7-gliedrigen gesättigten carbocyclischen Ring oder einen alkylsubstituierten 5-bis 7-gliedrigen gesättigten carbocyclischen Ring mit bis zu 18 Kohlenstoffatomen darstellen können. 



   RI kann beispielsweise für Wasserstoff, Methyl, Äthyl, Isopropyl,   tert.-Butyl, Cyclopentyl,   Cyclohexyl, Octyl, Dodecyl, Octadecyl" Benzyl, Phenyläthyl, Phenylbutyl, Phenyloctyl, Dimethylbenzyl, Dibutylbenzyl,   Octylbenzyl,     Nonylbenzyl,   Dimethylaminoäthyl, 2-Dimethylaminoisobutyl, Diäthylaminoäthyl, Dibutylaminoäthyl, Dipentylaminoäthyl und Furfuryl stehen. 
 EMI1.2 
    stehthexyl,   Octyl, Decyl, Dodecyl, Octadecyl, Phenyl, Naphthyl, Chlorphenyl, Dichlorphenyl, Butylphenyl.

   Dibutylphenyl, Octylphenyl, Nonylphenyl, Methoxyphenyl,   tert.-Butoxyphenyl, Octoxyphenyl,   Chlornaphthyl, Butylnaphthyl, Octylnaphthyl, Methoxynaphthyl, Äthoxynaphthyl, Benzyl, Phenyl- äthyl, Phenylbutyl, Phenyloctyl, Dimethylbenzyl, Dibutylbenzyl, Octylbenzyl, Nonylbenzyl und 2-Furyl stehen. 

 <Desc/Clms Page number 2> 

 



   Weiters können   R   und   R   zusammen, unter Einschluss des Kohlenstoffatoms, an welches sie gebunden sind, Pentamethylen-, Hexamethylen- oder Heptamethylenringe darstellen, an welche ein oder 
 EMI2.1 
 den sind, beispielsweise Pentamethylen-, Hexamethylen- oder Heptamethylenringe darstellen, an welche ein oder mehrere Alkylsubstituenten, wie   z. B. Methyl-, Äthyl-oder   Butylgruppen gebunden sein können. In diesem Falle sind R4 und   R5   auf insgesamt 18 Kohlenstoffatome begrenzt. 



   Erfindungsgemäss werden die N-Vinyl-2-piperazinone hergestellt, indem man in Gegenwart eines stark basischen Vinylierungskatalysators und bei einer Temperatur im Bereich von etwa 100 bis etwa 2500 C Acetylen und ein 2-Piperazinon der allgemeinen Formel 
 EMI2.2 
 
 EMI2.3 
 

 <Desc/Clms Page number 3> 

 



      RBeispiel l :   Aus 193 Teilen   3, 3-Dimethyl-2-piperazinon   in 750 Teilen N-Methylpyrrolidinon und 14, 8 Teilen   Kaliumisopropo ? Cyd ( (10Mol-O/o,   bezogen auf das Piperazinon), zugesetzt als   25% ige   Lösung in 2-Propanol, wird eine Lösung hergestellt. 



   Das Gemisch wird   auf 120 C   abgekühlt und bei dieser Temperatur mit Acetylen bei    17, 5 kg/cm'ge-   sättigt. Sodann wird es unter konstantem Fluss und unter Rühren und Druck durch   einen auf 1900 C gehaltenen   Reaktor in einer solchen Geschwindigkeit gepumpt, dass die durchschnittliche Verweilzeit bei dieser Temperatur 10 min beträgt. Das rohe Reaktorprodukt wird einer Kurzwegdestillation unterworfen, um nieder siedende Fraktionen zu entfernen, wonach der Rückstand destilliert wird. Man erhält 95 Teile einer bei 950 C bei 0, 5 mm Hg siedenden Flüssigkeit, welche gemäss Analyse 3, 3-Dimethyl-l-vinyl-   - 2-piperazinon darstellt. Das Produkt wird   nochmals destilliert und siedet bei 79-80 C bei   0, 11mm   Hg, 
 EMI3.1 
 gegebenenfalls weiter gereinigt werden. 



   Beispiel 2 : Aus 50 Teilen 2-Piperazinon und 120 Teilen N-Methylpyrrolidinon wird ein Gemisch hergestellt, in welchem 3 Teile metallisches Kalium gelöst werden. Dieses Gemisch'wird in einen Druckreaktor   eingebracht, welcher druckgeprüft   und zuerst mit Stickstoff und sodann mit Acetylen gespült wird. Das Gemisch wird unter einem Acetylendruck von 28 kg/cm2 so lange auf   129-152    C erhitzt, bis die Acetylenabsorption unerheblich wird (etwa 100 min). Der Reaktor wird sodann abgekühlt, entlüftet und geöffnet. Das Reaktionsprodukt wird einer Kurzwegdestillation unterworfen, um die nieder siedenden Fraktionen zu entfernen, wonach das Produkt in einem weiten Bereich von 55 bis   1090   C bei 0, 3 mm Hg destilliert wird.

   Diese Fraktion wird sorgfältig redestilliert, wobei 15 Teile einer farblosen Flüssigkeit mit einem Siedepunkt von 91 bis 930 C bei 0, 12 mm Hg,   nD 25 1, 540.   erhalten werden. 



  Diese Flüssigkeit ist gemäss Analyse   1- Vinyl-2-piperazinon.   

**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.

Claims (1)

  1. PATENTANSPRÜCHE : 1. Verfahren zur Herstellung von neuen N-Vinyl-2-piperazinonen der allgemeinen Formel EMI3.2 worin RI für Wasserstoff, Alkyl oder Cycloalkyl mit bis zu 18 Kohlenstoffatomen. Aralkyl oder alkylsubstituiertes Aralkyl mit bis zu 18 Kohlenstoffatomen, Dialkylaminoalkyl mit bis zu 12 Kohlenstoff- atomen, worin jede der erwähnten Alkylgruppe bis zu 8 Kohlenstoffatomen enthält, oder Furfuryl steht, R Wasserstoff oder Methyl darstellt, R Wasserstoff, Alkyl oder Cycloalkyl mit bis zu 18 Kohlenstoff- atomen, Phenyl, Naphthyl, Aralkyl oder alkylsubstituiertes Aralkyl mit bis zu 18 Kohlenstoffatomen, 2-Furyl oder alkyl-, chlor-und alkoxysubstituiertes Phenyl und Naphthyl, worin der Alkylanteil bis zu 18 Kohlenstoffatome enthält, bedeutet,
    R Wasserstoff oder Alkyl mit bis zu 4 Kohlenstoffatomen darstellt und R5 Wasserstoff oder Alkyl mit bis zu 4 Kohlenstoffatomen ist, bzw. R2 und R 3 zusammen einschliesslich des Kohlenstoffatoms, an welches sie gebunden sind, einen 5-bis 7-gliedrigen gesättigten carbocyclischen Ring oder einen alkylsubstituierten 5-bis 7-gliedrigen gesättigten carbocyclischen Ring mit bis zu 18 Kohlenstoffatomen bilden können, bzw.
    R'und R5 zusammen mit dem Kohlenstoffatom, an welches sie gebunden sind, einen 5-bis 7-gliedrigen gesättigten carbocyclischen Ring oder einen alkylsubstituierten 5-bis 7-gliedrigen gesättigten carbocyclischen Ring mit bis zu 18 Kohlenstoffatomen EMI3.3 Vinylierungskatalysators und bei Temperaturen im Bereich von etwa 100 bis etwa 2500 C Acetylen und ein 2-Piperazinon der allgemeinen Formel <Desc/Clms Page number 4> EMI4.1 worin R1,R2,R3,R4 und R5 obgenannte Bedeutung haben, umsetzt.
    2. Verfahren nach Anspruch l, dadurch gekennzeichnet, dass als stark basischer Vinylierungskatalysator ein Alkalimetall oder ein Hydroxyd oder Alkoxyd hievon verwendet wird.
    3. Verfahren nach Anspruch 2, dadurch gekennzeichnet, dass als Alkalimetall Natrium oder Kalium und als Alkalialkoxyd Natriummethoxyd oder Kaliummethoxyd eingesetzt wird.
    4. Verfahren nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass die Reaktion bei Temperaturen im Bereich von 130 bis 2200 C durchgeführt wird.
    5. Verfahren nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass die Reaktion in Gegenwart eines inerten organischen Lösungsmittels durchgeführt wird.
AT180465A 1964-03-04 1965-03-01 Verfahren zur Herstellung von neuen N-Vinyl-2-piperazinonen AT260936B (de)

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US3386998A (en) * 1964-05-19 1968-06-04 Rohm & Haas Nu-alkenoyloxy-2-morpholinones and their corresponding hydrolysis products
US4123408A (en) * 1976-11-26 1978-10-31 American Optical Corporation Hydrogel contact lens
US4123407A (en) * 1976-11-26 1978-10-31 American Optical Corporation Hydrophilic contact lens
US4190571A (en) * 1977-09-21 1980-02-26 The B. F. Goodrich Company Substituted 2-keto-1,4-diazacycloalkanes and UV-light-stabilized compositions containing them
US4170650A (en) * 1978-05-22 1979-10-09 The Dow Chemical Company Oxopiperazinium salts, their preparation and their use
DE3132882A1 (de) * 1981-08-20 1983-03-03 Cassella Ag, 6000 Frankfurt Neue piperazinone, ihre herstellung und verwendung
DE3817198A1 (de) * 1988-05-20 1989-11-30 Cassella Ag Thienyl-piperazinone, ihre herstellung und verwendung
US5882799A (en) * 1996-12-16 1999-03-16 Vernay Laboratories, Inc. Polymeric coupling agents for the adhesion of macromolecular materials and metal substrates
US20070122443A1 (en) * 2005-11-29 2007-05-31 Narayanan Pallassana V Amphiphilic copolymer compositions

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US2944974A (en) * 1956-12-31 1960-07-12 Shell Oil Co Lubricating oil compositions
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FR1431211A (fr) 1966-03-11
GB1094724A (en) 1967-12-13
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BR6567402D0 (pt) 1973-10-23
DE1620149A1 (de) 1970-04-30
IL23092A (en) 1968-11-27
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AT261216B (de) 1968-04-10
US3390139A (en) 1966-03-11

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