DE966955C - Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile - Google Patents

Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile

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Publication number
DE966955C
DE966955C DEC2483D DEC0002483D DE966955C DE 966955 C DE966955 C DE 966955C DE C2483 D DEC2483 D DE C2483D DE C0002483 D DEC0002483 D DE C0002483D DE 966955 C DE966955 C DE 966955C
Authority
DE
Germany
Prior art keywords
acrylic acid
saponifying
preparation
acid amide
amide
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
Application number
DEC2483D
Other languages
German (de)
Inventor
Dr Rudolf Mueller
Dr Werner Zerweck
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cassella Farbwerke Mainkur AG
Original Assignee
Cassella Farbwerke Mainkur AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cassella Farbwerke Mainkur AG filed Critical Cassella Farbwerke Mainkur AG
Priority to DEC2483D priority Critical patent/DE966955C/en
Application granted granted Critical
Publication of DE966955C publication Critical patent/DE966955C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

(WiGBl. S. 175)(WiGBl. P. 175)

AUSGEGEBEN AM 19. SEPTEMBER 1957ISSUED SEPTEMBER 19, 1957

C 2483 IVb j 12C 2483 IVb j 12

von Acrylsäurenitrilof acrylonitrile

(Ges. v. 15. 7.1951)(Ges. Of 15.7.1951)

Es wurde gefunden;, daß man Acrylsäureamid, das man nach den Angaben des Schrifttums seither durch Einwirkung von Ammoniak auf Acrylsäure^ chloirid hergestellt hat, im vorzüglicher Ausbeute und Reinheit, ausgehend von, dem großtechnisch leicht zugänglichen! Acrylsäurenitril, erhalten kann, wenn man auf dieses ι Mol Wasser in Gegenwart von ι Mol Schwefelsäure (H2SO4) einwirken läßt.It has been found that acrylic acid amide, which, according to the information in the literature, has since been produced by the action of ammonia on acrylic acid chloiride, in excellent yield and purity, starting from the industrially easily accessible! Acrylonitrile can be obtained if this ι mol of water is allowed to act in the presence of ι mol of sulfuric acid (H 2 SO 4 ).

Der besondere Vorteil des. Verfahrens besteht darin, daß man das Acrylsäurenitril in einem einzigen Arbeitsgang in das Amid überführen, kann, und zwar in fast quantitativer Ausbeute und ohne daß eine Anlagerung der Schwefelsäure an die doppelte Kohl ens toffbindung des Acrylsäurenitrilserfolgte. The particular advantage of the. The process is that the acrylonitrile in one convert a single operation into the amide, and in almost quantitative yield and without any addition of the sulfuric acid to the double carbon bond of the acrylonitrile.

Zweckmäßig setzt man dem Reaktionsgemisch einen Körper zu, der die Polymerisation, der Acrylsäurerverbindungeni verhindert. Die entstandene Reaktionsmasse wird zweckmäßig mit Alkalien zersetzt, und zwar vorteilhaft mit Ätzkalk oder Calciumcarbonat, damit die Schwefelsäure als unlösliches Calciumsulfat aus dem Reiaktionsgemisch durch. Filtration entfernt werden kann. Das Acrylsäureamid kann aus der erhaltenen wäßrigen Lösung durch Eindampfen, abgeschieden oder durch Extrahieren mit organischen Lösungs-A body is expediently added to the reaction mixture, which the polymerization, the acrylic acid compoundsi prevented. The resulting reaction mass is expediently decomposed with alkalis, advantageously with quick lime or Calcium carbonate so that the sulfuric acid as insoluble calcium sulfate from the reaction mixture. Filtration can be removed. The acrylic acid amide can be deposited from the aqueous solution obtained by evaporation or by extraction with organic solvents

709 682/97709 682/97

mitteln1 abgetrennt werden. Für den Hauptverwendungszweck des Acrylsäureiamids als Teilnehmer einer Polymerisationsreaktion kann die anfallende wäßrige Lösung unmittelbar benutzt wenden.means 1 are separated. For the main purpose of the acrylic acid amide as a participant in a polymerization reaction, the resulting aqueous solution can be used immediately.

Beispiel ιExample ι

In eine Mischung von, 300 Teilen Schwer eis äuremonohydrat und 4,5 Teilen, Schwefel werden unter gutem Rühren bei einer Temperatur von. 40 bis 65° gleichzeitig 54 Teile Wasser und 159 Teile Acrylnitril eingetropft. Nachdem alles zugegeben ist, wird zur Beendigung der Reaktion, noch 3 bis 4 Stunden: bei 60 bis yo° nachgerührt. Die entstandene Reaktionsmasse wird mit kaltem Wasser versetzt, vom Schwefel abfiltriert und mit Kreide neutralisiert. Nach dem Absaugen und Nachwaschen mit Wasser wird die Lösung im Vakuum eingeengt und das. zurückbleibende Rohamid mit organischen; Lösungsmitteln, wie Benzol oder Methylenchlorid, aufgenommen. Das daraus auskristallisierte Acrylsäureamid fällt rein, an. Fp. 82 bis 830.In a mixture of 300 parts of heavy ice acid monohydrate and 4.5 parts of sulfur are stirred at a temperature of. 40 to 65 ° at the same time 54 parts of water and 159 parts of acrylonitrile were added dropwise. After everything has been added, to end the reaction, stirring is continued for 3 to 4 hours at 60 to 90 degrees . The resulting reaction mass is mixed with cold water, filtered off from the sulfur and neutralized with chalk. After suctioning off and washing with water, the solution is concentrated in vacuo and the remaining crude amide with organic; Solvents such as benzene or methylene chloride added. The acrylic acid amide which crystallizes out is obtained in pure form. Mp. 82-83 0th

Das· bei der Reaktion in nahezu theoretischer Ausbeute entstehende Acrylsäureamid kann für die meisten Verwendungszwecke, wie beispielsweise Polymerisation oder Mischpolymerisation, in wäßriger Lösung sofort weiter verarbeitet werden.That · in the reaction in almost theoretical Yield resulting acrylic acid amide can be used for most purposes, such as Polymerization or copolymerization, in aqueous solution, can be processed further immediately.

Beispiel 2Example 2

200 Teile Schwefelsäuremonohydrat werden mit 36 Teilen Wasser versetzt. Unter gutem Rühren werden bei 10 bis 200 106 Teile Acrylnitril eingetropft. Nachdem alles eingetropft ist, wird in 2 bis 3 Stunden a,uf 60 bis 65° angewärmt und bis zur vollständigen Amidbildung noch einige Stunden bei 60 bis 700 verrührt. Die Aufarbeitung erfolgt wie im Beispiel 1. Die Ausbeute an monomeretn Acrylsäureamid beiträgt 90% der Theorie.200 parts of sulfuric acid monohydrate are mixed with 36 parts of water. With good stirring, acrylonitrile are added dropwise at 10 to 20 0 106 parts. After everything is dripped, is heated and uf 60 to 65 ° stirred until complete amide formation a few more hours at 60 to 70 0 to 2 to 3 hours a. The work-up is carried out as in Example 1. The yield of monomeric acrylic acid amide accounts for 90% of theory.

Claims (1)

PATENTANSPRUCH:PATENT CLAIM: Verfahren zur Darstellung von Acrylsäureamid durch Verseifen von Acrylsäurenitril mit Schwefelsäure, dadurch gekennzeichnet, daß man auf 1 Mol Acrylsäurenitril 1 Mol Wasser in Gegenwart von· 1 Mol Schwefelsäure (H2SO4) einwirken läßt.Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile with sulfuric acid, characterized in that 1 mole of water is allowed to act on 1 mole of acrylic acid nitrile in the presence of · 1 mole of sulfuric acid (H 2 SO 4 ). In, Betracht gezogene Druckschriften:In, considered publications: Deutsche Patentschrift Nr. 672 490;
britische Patentschrift Nr. 456 533;
»Chem. Zentralblatt«, 1927, I, S. 881; 1931, I, S. 2036/2037; 1931, II, S. 3456;German Patent No. 672 490;
British Patent No. 456,533;
“Chem. Zentralblatt «, 1927, I, p. 881; 1931, I, pp. 2036/2037; 1931, II, p. 3456; »Bull. Soc. chim. Belg.«, 39 (1930), S. 563.“Bull. Soc. chim. Belg. ", 39 (1930), p. 563. ©709 682/97 9.5T© 709 682/97 9.5T
DEC2483D 1942-09-26 1942-09-26 Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile Expired DE966955C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEC2483D DE966955C (en) 1942-09-26 1942-09-26 Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEC2483D DE966955C (en) 1942-09-26 1942-09-26 Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile

Publications (1)

Publication Number Publication Date
DE966955C true DE966955C (en) 1957-09-19

Family

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DEC2483D Expired DE966955C (en) 1942-09-26 1942-09-26 Process for the preparation of acrylic acid amide by saponifying acrylic acid nitrile

Country Status (1)

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DE (1) DE966955C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3041375A (en) * 1959-07-06 1962-06-26 Dow Chemical Co Preparation of acrylamide
DE1156787B (en) * 1958-08-22 1963-11-07 Henkel & Cie Gmbh Process for the continuous production of acrylic acid amide by saponification of acrylic acid nitrile with sulfuric acid and water
DE1180364B (en) * 1958-03-14 1964-10-29 Stockhausen & Cie Chem Fab Process for the continuous production of acrylic acid alkyl esters from acrylic acid nitrile
DE1298989B (en) * 1964-03-13 1969-07-10 Dow Chemical Co Process for the production of acrylic or methacrylic acid amide sulfate

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB456533A (en) * 1935-05-10 1936-11-10 John William Croom Crawford Improvements in or relating to the manufacture of unsaturated organic compounds
DE672490C (en) * 1934-07-09 1939-03-04 Ici Ltd Process for the production of methacrylamide or its sulfate

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE672490C (en) * 1934-07-09 1939-03-04 Ici Ltd Process for the production of methacrylamide or its sulfate
GB456533A (en) * 1935-05-10 1936-11-10 John William Croom Crawford Improvements in or relating to the manufacture of unsaturated organic compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1180364B (en) * 1958-03-14 1964-10-29 Stockhausen & Cie Chem Fab Process for the continuous production of acrylic acid alkyl esters from acrylic acid nitrile
DE1156787B (en) * 1958-08-22 1963-11-07 Henkel & Cie Gmbh Process for the continuous production of acrylic acid amide by saponification of acrylic acid nitrile with sulfuric acid and water
US3041375A (en) * 1959-07-06 1962-06-26 Dow Chemical Co Preparation of acrylamide
DE1298989B (en) * 1964-03-13 1969-07-10 Dow Chemical Co Process for the production of acrylic or methacrylic acid amide sulfate

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