DD201785A5 - PROCESS FOR THE PREPARATION OF AMINO PYRIDINES - Google Patents
PROCESS FOR THE PREPARATION OF AMINO PYRIDINES Download PDFInfo
- Publication number
- DD201785A5 DD201785A5 DD23851782A DD23851782A DD201785A5 DD 201785 A5 DD201785 A5 DD 201785A5 DD 23851782 A DD23851782 A DD 23851782A DD 23851782 A DD23851782 A DD 23851782A DD 201785 A5 DD201785 A5 DD 201785A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- catalyst
- amino
- hydrogen
- preparation
- picoline
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Amino-Pyridine werden beim Behandeln von Glutarsaeuredinitrilen mit H tief 2 in Gegenwart von Pd-Katalysatoren auf alfa-AL tief 2 O tief 2-Traegern in der Gasphase bei Temperatturen von260 bis 310 Grad C hergrstellt.Amino-pyridines are prepared by treating glutaric acid dinitriles with H 2 in the presence of Pd catalysts on alfa-AL deep 2 O deep 2-gels in the gas phase at temperatures of 260 to 310 ° C.
Description
-J--J-
Verfahren zur Herstellung von Amino-PyridinenProcess for the preparation of amino-pyridines
Die vorliegende Erfindung betrifft die Herstellung von Amino-Pyridinen der allgemeinen FormelThe present invention relates to the preparation of amino-pyridines of the general formula
in welcher R ein Wasserstoffatom oder einen niedrigen Alkylrest mit 1 bis 2 C-Atomen bedeutet.in which R represents a hydrogen atom or a lower alkyl radical having 1 to 2 C atoms.
Charakteristik del bekannten technischen Lösungen Amino-Pyridine stellen Ausgangsmaterialien für die Herstellung chemotherapeutisch wirksamer Substanzen und pharmako- . Characteristics of the known technical solutions Amino-pyridines provide starting materials for the production of chemotherapeutically active substances and pharmaco-.
logisch bedeutsamer Verbindungen dar.logically significant connections.
Das Verfahren der Erfindung ist dadurch gekennzeichnet, dass man Glutarsäuredinitril der allgemeinen FormelThe process of the invention is characterized in that glutaric acid dinitrile of the general formula
NC CN in der R ein Wasserstoffatom oder einen niedrigen Alkylrest mit 1 bis 2 C-Atomen bedeutet, in der Gasphase, zusammen mit Wasserstoff bei Temperaturen von 260 bis 3100C über einen Pt- oder Pd-Katalysator, der auf einen' α-ΑΙ-,Ο -Träger aufgebracht ist, leitet.NC CN in which R is a hydrogen atom or a lower alkyl radical having 1 to 2 C atoms, in the gas phase, together with hydrogen at temperatures of 260 to 310 0 C via a Pt or Pd catalyst, which on an 'α- ΑΙ-, Ο-carrier is applied, conducts.
Neben Glutarsäuredinitril können auch substituierte Glutarsäuredinitrile, vorzugsweise 2-Methylglutarsäuredinitril, zur Anwendung komiuen. Eine ganz besonders vorteilhafte Ausgestaltung der Erfindung ist es, wenn 2-MethylglutarsäuredinitrilIn addition to glutaric acid dinitrile, it is also possible to use substituted glutaric acid dinitriles, preferably 2-methylglutaronitrile. A particularly advantageous embodiment of the invention is when 2-methylglutaronitrile
umgesetzt werden soll, von einem Gemisch von Methylglutarsäuredinitril und Alky!bernsteinsäuredinitril auszugehen, wie es als Nebenprodukt bei der Adipinsäuredinitrilherstellung anfällt.is to be reacted, starting from a mixture of methylglutaronitrile and Alky! succinonitrile, as obtained as a byproduct in the adiponitrile production.
Das Glutarsäuredinitril wird zweckmässig in einer' Menge von 0,1 bis 1,0 g, vorzugsweise von 0,3 bis 0,5 g pro Gramm Katalysator und pro Stunde, eingesetzt.The glutaronitrile is conveniently used in an amount of from 0.1 to 1.0 g, preferably from 0.3 to 0.5 g per gram of catalyst per hour.
Die Menge an Wasserstoff liegt vorteilhaft bei 0,5 bis 1,0 Liter Wasserstoff pro Gramm Katalysator und pro Stunde.The amount of hydrogen is advantageously from 0.5 to 1.0 liter of hydrogen per gram of catalyst per hour.
Die Reaktionstemperatur liegt vorteilhaft bei 280 bis 3000C.The reaction temperature is advantageously from 280 to 300 ° C.
Als Katalysator kommt Platin oder Palladium zum Einsatz, das in Mengen von 1 bis 10 Gew.-%, vorzugsweise 1 bis 5 Gew.-%, auf einen Träger aus-c-Al O aufgebracht wird.The catalyst used is platinum or palladium, which is applied in amounts of from 1 to 10% by weight, preferably from 1 to 5% by weight, to a support of c-Al-O.
Als α-Α1_Ο als Träger kommt zweckmässig solches q-A1 O in Frage, das eine spezifische Oberfläche von 100 rn /gAs α-Α1_Ο as a carrier is suitably such q-A1 O in question, which has a specific surface area of 100 rn / g
2 2 22 2 2
bis 350 m /g, vorzugsweise 250 m /g bis 300 m /g, aufweist.to 350 m / g, preferably 250 m / g to 300 m / g.
Das auf Reaktionstemperatur erhitzte Gemisch aus Glutarsäuredinitril und Wasserstoff wird über oder durch den Katalysator-Träger geleitet. Dabei kann der Katalysator-Träger als Festbett oder als Fliessbett vorliegen.The heated to reaction temperature mixture of glutarodinitrile and hydrogen is passed over or through the catalyst support. In this case, the catalyst support may be present as a fixed bed or as a fluidized bed.
Das nach dem Verfahren der Erfindung anfallende Reaktionsgemisch besteht- ausTnichturngesetztein ÄU"3ganjgSmaterd..äl ^das wiederThe reaction mixture obtained by the process of the invention consists of non-reacted compounds in the form of a solid material
zurückgewonnen wird: Aminopyridine und andere Pyridinbasen. Bei Glutarsäuredinitril fallen neben dem 2-Aminopyridin noch grössere Mengen Pyridin und' Butyronitril an, die abgetrennt und weiterverwertet werden können. Geht man von Methylglutardinitril aus, fallen neben 2-Amino-3-picolin und 6-Amino-3-picolin noch grössere Mengen 3-Picolin an, die abgetrennt und einem weiteren Verwendungszweck zugeführt werden.recovered: aminopyridines and other pyridine bases. In addition to 2-aminopyridine, glutarodinitrile produces even greater amounts of pyridine and butyronitrile, which can be separated off and reused. If methylglutaronitrile is used, in addition to 2-amino-3-picoline and 6-amino-3-picoline, even larger amounts of 3-picoline are precipitated, which are separated off and fed to a further intended use.
210,4 g einer Mischung aus 86,4% 2-Methylglutarsäuredinitril und 13,2% Aetylsuccinodinitril, wie sie bei der Adipinsäuredinitrilsynthese als Nebenprodukt anfällt, wurden bei 28O0C zusammen mit 30 Liter H pro Stunde während 10 Stunden durch ein Katalysatorbett aus Pd auf g-AljO, (5% Pd) in Kugelform gepumpt. Nach Auffangen des Reaktionsproduktes (194,9 g) wurden folgende Produkte isoliert:210.4 g of a mixture of 86.4% 2-methylglutaronitrile and 13.2% Aetylsuccinodinitril, as obtained in the adiponitrile as a byproduct, were at 28O 0 C together with 30 liters of H per hour for 10 hours through a catalyst bed of Pd pumped on g-AljO, (5% Pd) in spherical form. After collecting the reaction product (194.9 g), the following products were isolated:
23% nicht umgesetztes Methylglutarsäuredinitril 23% 2-Amino-3-picolin23% unreacted methyl glutaronitrile 23% 2-amino-3-picoline
14% 6-Amino-3-picolin14% 6-amino-3-picoline
14% Picolin14% picoline
ferner noch etwa 17% Valero- und 2-Methylbutyronitril.further about 17% of valero and 2-methylbutyronitrile.
Für einen Umsatz von ca. 75% erhielt man Aminopicoline in einer Ausbeute von 54% und 3-Picolin in einer Ausbeute von 22%.For a conversion of about 75%, aminopicolines were obtained in a yield of 54% and 3-picoline in a yield of 22%.
Aehnlich wie in Beispiel 1, aber bei 3100C, wurden während 6 Stunden Glutarsäuredinitril zusammen mit 20 Liter H-/g Katalysator/h durch den Katalysator gepumpt. Es resultierte 2-Aminopyridin in einer Ausbeute von 26,9%. Daneben wurden 29,9% Pyridin gefunden.Similar to Example 1, but at 310 0 C, glutarodinitrile were pumped through the catalyst together with 20 liters H / g catalyst / h during 6 hours. This resulted in 2-aminopyridine in a yield of 26.9%. In addition, 29.9% pyridine was found.
Beispiele 3-5Examples 3-5
ι ιι ι
Im'Gegensatz zu den Beispielen 1,2,3,4 und 5 kam hier ein Platinkatalysator zum Einsatz: 1 % Pt auf einem Träger aus α-Al 0 Im Prinzip aber wurde gleich wie in vorangehenden Beispielen gearbeitet.In contrast to Examples 1, 2, 3, 4 and 5, a platinum catalyst was used here: 1% Pt on a support of α-Al 0 In principle, however, the same procedure was used as in the preceding examples.
Claims (5)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH216681 | 1981-03-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
DD201785A5 true DD201785A5 (en) | 1983-08-10 |
Family
ID=4227424
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD23851782A DD201785A5 (en) | 1981-03-31 | 1982-03-29 | PROCESS FOR THE PREPARATION OF AMINO PYRIDINES |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0062264A3 (en) |
JP (1) | JPS57175167A (en) |
BR (1) | BR8201760A (en) |
DD (1) | DD201785A5 (en) |
DK (1) | DK145182A (en) |
ES (1) | ES8303347A1 (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4935521A (en) * | 1989-04-06 | 1990-06-19 | E. I. Du Pont De Nemours And Company | Preparation of 3-picoline |
US5066809A (en) * | 1990-09-27 | 1991-11-19 | The Standard Oil Company | Preparation of 3-methylpyridine from 2-methylglutaronitrile |
US8022167B2 (en) | 2006-12-21 | 2011-09-20 | Aaron Minter | Process for the synthesis of diaminopyridines from glutaronitriles |
-
1982
- 1982-03-26 EP EP82102584A patent/EP0062264A3/en not_active Withdrawn
- 1982-03-29 BR BR8201760A patent/BR8201760A/en unknown
- 1982-03-29 DD DD23851782A patent/DD201785A5/en unknown
- 1982-03-30 DK DK145182A patent/DK145182A/en not_active IP Right Cessation
- 1982-03-30 JP JP5219682A patent/JPS57175167A/en active Pending
- 1982-03-30 ES ES510945A patent/ES8303347A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DK145182A (en) | 1982-10-01 |
EP0062264A3 (en) | 1983-06-01 |
JPS57175167A (en) | 1982-10-28 |
ES510945A0 (en) | 1983-02-01 |
BR8201760A (en) | 1983-03-01 |
EP0062264A2 (en) | 1982-10-13 |
ES8303347A1 (en) | 1983-02-01 |
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