DE817913C - Process for the production of piperazine - Google Patents

Process for the production of piperazine

Info

Publication number
DE817913C
DE817913C DES2669A DES0002669A DE817913C DE 817913 C DE817913 C DE 817913C DE S2669 A DES2669 A DE S2669A DE S0002669 A DES0002669 A DE S0002669A DE 817913 C DE817913 C DE 817913C
Authority
DE
Germany
Prior art keywords
piperazine
production
acid
monoethanolamine
excess
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
DES2669A
Other languages
German (de)
Inventor
Igor Scriabine
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.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
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 Rhone Poulenc SA filed Critical Rhone Poulenc SA
Application granted granted Critical
Publication of DE817913C publication Critical patent/DE817913C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/023—Preparation; Separation; Stabilisation; Use of additives

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Description

Verfahren zur Herstellung von Piperazin Es wurde gefunden, daß man beim Erhitzen von Halogenhydraten des Monoäthanolamins das entsprechende Halogenhydrat des Piperazins mit beachtlichen Ausbeuten erhält Diese Reaktion findet beim Erhitzen von Halogenhydraten des Monoäthanolamins auf Zoo bis 270°, vorzugsweise bei 22o bis 25o° statt und kann ohne Zusatz von Katalysatoren verlaufen, doch ist der Zusatz von dehydratisierenden Katalysatoren, wie Chloriden, Bromiden, Jodiden von Zn, Fe, Al, Mg, Borsäure usw., zu empfehlen. Der Zusatz von Alkalijodiden begünstigt die Kondensation.Process for the preparation of piperazine It has been found that the corresponding halohydrate of piperazine is obtained in considerable yields when the halohydrates of monoethanolamine are heated This reaction takes place when the monoethanolamine halohydrates are heated up to 270 °, preferably at 22o to 25o °, and can take place without the addition of catalysts, but the addition of dehydrating catalysts such as chlorides, bromides, iodides of Zn, Fe, Al , Mg, boric acid, etc., recommended. The addition of alkali iodides promotes condensation.

Das Verhältnis der Halogenwasserstoffsäuremenge zum blonoäthanolamin kann variieren. Man kann sowohl die zur Bildung des Halogenhydrats erforderliche theoretische Menge an Säure, wie auch eine etwas darunterliegende oder überschüssige Säuremenge verwenden.The ratio of the amount of hydrohalic acid to the blonoethanolamine may vary. One can use both those required for the formation of the halohydrate theoretical amount of acid, as well as a somewhat lower or excess Use amount of acid.

Die Isolierung des Piperazins aus dem Reaktionsgemisch kann nach allen geeigneten Methoden erfolgen, z. B. durch Destillation der Basen mit Wasserdampf in Gegenwart von Alkaliüberschuß und Rektifizierung der destillierten Basen, Fällung des Piperazins in Form eines unlöslichen Salzes, z. B. als Oxalat, Fällung des Piperazins in Form seines Dinitrosoderivats und Regenerierung des letzteren zum Piperazin mittels Hydrolyse. Vorzugsweise benutzt man zu dieser Isolierung die kürzlich entdeckte Eigenschaft des Piperazinchlorhydrates (vgl. französische Patentschrift 913 98i), mit Ammoniumchlorid in Gegenwart von ChloridüberschuB ein wenig lösliches Doppelchlorhydrat zu bilden, das leicht kristallisiert.The isolation of the piperazine from the reaction mixture can after all suitable methods, e.g. B. by distilling the bases with steam in the presence of excess alkali and rectification of the distilled bases, precipitation of piperazine in the form of an insoluble salt, e.g. B. as oxalate, precipitation of piperazine in the form of its dinitroso derivative and regeneration of the latter to piperazine by means of hydrolysis. Preferably one uses for this isolation the recently discovered property of piperazine chlorohydrate (cf. French patent specification 913 98i), a little soluble with ammonium chloride in the presence of excess chloride To form double chlorohydrate, which easily crystallizes.

Das folgende Beispiel erläutert die vorliegende Erfindung.The following example illustrates the present invention.

Beispiel Zu 3o5 Gewichtsteilen Monoäthanolamin gibt man unter Kühlung ii8o Teile Salzsäure (D. = i,18) und fügt ioo Teile Magnesiumchlorid hinzu. Man kocht 3 Stunden am Rückfluß, destilliert den Säureüberschuß ab und erhitzt den Rückstand 24 Stunden auf 23o bis 24o°.EXAMPLE To 3o5 parts by weight of monoethanolamine is added with cooling 100 parts hydrochloric acid (D. = 1.18) and add 100 parts magnesium chloride. Man refluxed for 3 hours, the excess acid was distilled off and the residue was heated 24 hours at 23o to 24o °.

Durch geeignete Behandlung isoliert man aus dem Reaktionsgemisch 12o Teile wasserfreien Piperazins.A suitable treatment is used to isolate 12o from the reaction mixture Share anhydrous piperazine.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Piperazin, dadurch gekennzeichnet, daB man ein Halogenhydrat des Monoäthanolamins auf Zoo bis 270° erhitzt, gegebenenfalls in Gegenwart dehydratisierender Katalysatoren. Claim: Process for the production of piperazine, characterized in that a halohydrate of monoethanolamine is heated to a temperature of up to 270 °, optionally in the presence of dehydrating catalysts.
DES2669A 1944-04-21 1950-04-06 Process for the production of piperazine Expired DE817913C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR817913X 1944-04-21

Publications (1)

Publication Number Publication Date
DE817913C true DE817913C (en) 1951-10-22

Family

ID=9268586

Family Applications (1)

Application Number Title Priority Date Filing Date
DES2669A Expired DE817913C (en) 1944-04-21 1950-04-06 Process for the production of piperazine

Country Status (1)

Country Link
DE (1) DE817913C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2868791A (en) * 1954-10-19 1959-01-13 Union Carbide Corp Process for the production of substituted piperazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2868791A (en) * 1954-10-19 1959-01-13 Union Carbide Corp Process for the production of substituted piperazines

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