DE523602C - Process for the preparation of pyridine bases - Google Patents

Process for the preparation of pyridine bases

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Publication number
DE523602C
DE523602C DEI35652D DEI0035652D DE523602C DE 523602 C DE523602 C DE 523602C DE I35652 D DEI35652 D DE I35652D DE I0035652 D DEI0035652 D DE I0035652D DE 523602 C DE523602 C DE 523602C
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Germany
Prior art keywords
acetylene
ammonia
mixture
pyridine bases
predominantly
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
DEI35652D
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German (de)
Inventor
Dr Hans Roetger
Dr Leo Schlecht
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI35652D priority Critical patent/DE523602C/en
Application granted granted Critical
Publication of DE523602C publication Critical patent/DE523602C/en
Expired legal-status Critical Current

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    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
    • C07D213/10—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from acetaldehyde or cyclic polymers thereof
    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/08—Preparation by ring-closure
    • C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
    • C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Description

Verfahren zur: Herstellung von Pyridinbasen Nach den bisher 'bekannten Verfahren zur Darstellung von stickstoffhaltigen Kondensationsprodukten aus Acetylen und Ammoniak bei höheren Temperaturen in Gegenwart von Katalysatoren erhielt man durchweg als Hauptprodukt Nitrile, insbesondere Acetonitril. während Pyridinbasen meist nur in untergeordneten 11-iengen entstanden.Process for: Production of pyridine bases According to the previously known Process for the preparation of nitrogen-containing condensation products from acetylene and ammonia at higher temperatures in the presence of catalysts was obtained throughout the main product nitriles, especially acetonitrile. while pyridine bases mostly only emerged in subordinate 11-iengen.

Es wurde nun gefunden, daß man ein vorwiegend aus Pyridinbasen bestehendes Produkt erhält, wenn man ein Gemisch von Acetylen, Wasserdampf und Ammoniak oder ein Gemisch von Aldehvden, insbesondere Acetaldehyd, und Ammoniak für sich oder im Geinisch miteinander oder mit anderen Gasen oder Dämpfen vorteilhaft bei Temperaturen unterhalb 4oo° mit einer Geschwindigkeit über Katalysatoren leitet, die größer ist als die @ für die Bildung eines 'vorwiegend aus Nitrilen bestehenden Produktes erforderliche. Beim Arbeiten mit Aldehyden an Stelle von Acetylen als Ausgangsstoff kann ebenfalls Wasserdampf zugegen sein; dessen Anwesenheit ist jedoch in diesem Falle nicht erforderlich. Beim Arbeiten mit acetylenhaltigen Gasgemischen beträgt deren Wasserdampfgehalt vorteilhaft das Ein- bis Zweifache des Acetylengehaltes; ein höherer Wasserdampfgehalt, z. B. über ;o Volumprozent, ist weniger zweckmäßig.It has now been found that a predominantly pyridine base can be obtained Product obtained when a mixture of acetylene, steam and ammonia or a mixture of aldehydes, especially acetaldehyde, and ammonia alone or in combination with one another or with other gases or vapors, advantageously at temperatures below 4oo ° passes over catalysts at a speed that is greater than that required for the formation of a predominantly nitrile product. When working with aldehydes instead of acetylene as a starting material, you can also Water vapor be present; however, its presence is not required in this case. When working with acetylene-containing gas mixtures, their water vapor content is advantageously one to two times the acetylene content; a higher water vapor content, z. B. over; o percent by volume, is less useful.

Geeignete Kontaktmassen sind z. B. Bauxit und andere hydratwasserhaltige Stoffe, schwer reduzierbare Metallverbindungen, insbesondere des Zinks, oder auch Kombinationen dieser Stoffe, gegebenenfalls auch zusammen mit geeigneten Metallen.Suitable contact materials are e.g. B. Bauxite and other water-containing hydrates Substances, difficult to reducible metal compounds, especially zinc, or else Combinations of these substances, possibly also together with suitable metals.

Die optimale Strömungsgeschwindigkeit für die Bildung der Pyridinbasen ist abhängig von der Art und dem Verteilungsgrad der angewandten Kontaktmasse. Im allgemeinen erhält man mit gutwirkenden Kontaktmassen, z. B. auf Kieselsäuregel niedergeschlagenen Katalysatoren, bei einer Strömungsgeschwindigkeit von etwa ro bis 301 Acetylen pro Stunde und Liter Kontaktmasse gute Ausbeuten an Pyridinbasen. Bei Verwendung von Aldehyden können höhere Strömungsgeschwindigkeiten gewählt werden.The optimal flow rate for the formation of the pyridine bases depends on the type and degree of distribution of the contact compound used. in the in general, good-acting contact materials such. B. on silica gel precipitated catalysts, at a flow rate of about ro up to 301 acetylene per hour and liter of contact mass, good yields of pyridine bases. When using aldehydes, higher flow rates can be selected.

Man erhält bei dem vorliegenden Verfahren meist ein aus zwei Schichten bestehendes Kondensat, dessen ölige Schicht vorwiegend aus in Wasser schwer löslichen Pvridinbasen, wie Kollidinen und Lutidinen, besteht, während die wässerige Schicht neben geringen Mengen von Aldehydammoniak und Nitrilen vorwiegend wasserlösliche Pyridinabkömmlinge, insbesondere Picoline, enthält.In the present process, one of two layers is usually obtained existing condensate, the oily layer of which is predominantly made up of sparingly soluble in water Pvridine bases, like collidines and lutidines, exist while the watery layer in addition to small amounts of aldehyde ammonia and nitriles, mainly water-soluble Pyridine derivatives, especially picolines, contains.

Die .Bildung der Pyridinbasen gelingt in gleicher Weise aus reinen bzw. AldellydAminoniak-Geinischen wie aus technischen Gasgemischen. die die genannten Stoffe in Verdünnung mit anderen Gasen, z. B. Wasserstoff, Methan und Stickstoff, enthalten. oder auch aus gleichzeitig Acetylen und Aldehyd enthaltenden Gasen.The formation of the pyridine bases succeeds in the same way from pure or AldellydAminoniakeinischen such as from technical gas mixtures. which the said Substances diluted with other gases, e.g. B. hydrogen, methane and nitrogen, contain. or from the same time Containing acetylene and aldehyde Gases.

Die erhaltenen Produkte eignen sich, gegebenenfalls mich Fraktionierung und Reinigung, u. a. als Lösungsmittel und als Vergällu;lgsinittel für Alkohole u. dgl.The products obtained are suitable, optionally with fractionation and cleaning, i.a. as a solvent and as a denaturing agent for alcohols and the like

Beispiel i Ein Gemisch von gleichen Raumteilen Acetylen, Ammoniak und Wasserdampf wird mit einer Geschwindigkeit von q.o 1 je Stunde und Liter Kontaktmasse bei 350° über mit Zinksulfat beladenes Kieselsäuregel geleitet. Aus 2.40 1 Gasgemisch erhält man etwa i io ccm Kondensat, dessen ölige Schicht (55 ccm) in Wasser schwer lösliche Produkte darstellt, die zu über 75 °/o aus Pyridinbasen bestehen. Aus der wässerigen Schicht lassen sich weitere 30 ccm Py ridinbasen gewinnen.Example i A mixture of equal parts by volume of acetylene, ammonia and water vapor is passed at a rate of qo 1 per hour and liter of contact mass at 350 ° over silica gel loaded with zinc sulfate. From 2.40 l of gas mixture about io ccm of condensate is obtained, the oily layer (55 ccm) of which is sparingly water-soluble products, more than 75% of which consist of pyridine bases. A further 30 cc pyridine bases can be obtained from the aqueous layer.

Dieselbe Kontaktmasse liefert bei einer um die Hälfte verringerten Strömungsgeschwindigkeit des Gasgemisches unter sonst gleichen Bedingungen ein Kondensat, dessen Nitrilgehalt etwa das Achtfache des Gehaltes an Pyridinbasen beträgt.The same contact mass delivers with a reduced by half Flow rate of the gas mixture under otherwise identical conditions a condensate, whose nitrile content is about eight times the content of pyridine bases.

Beispiel e Ein technisches Gasgemisch, das aus etwa 5o'/" Wasserstoff, 2o0/, Wasserdampf, je io °/o Acetylen und Ammoniak und je 5'1" Stickstoff und Methan besteht, wird mit einer Geschwindigkeit von ioo 1 je Stunde und Liter Kontaktmasse über mit Zinkoxyd und Thoriumoxyd beladenes Kieselsäuregel bei 350° geleitet. Man erhält je Kubikmeter Acetylen etwa -8oo bis goo ccm Kondensat, das zu 8o °/o aus Pyridinbasen besteht.Example e A technical gas mixture that consists of about 50 '/ "hydrogen, 20% water vapor, 10% each of acetylene and ammonia, and 5'1 "each of nitrogen and methane exists, is at a rate of 100 per hour and liter of contact mass passed over silica gel loaded with zinc oxide and thorium oxide at 350 °. Man per cubic meter of acetylene receives about -8oo to 100 cc of condensate, 80 per cent of that from Pyridine bases.

Dieselbe Kontaktmasse liefert bei einer um die Hälfte verringerten Strömungsgeschwindigkeit des Gasgemisches unter sonst gleichen Bedingungen ein Produkt, das aus etwa 50 'to Pyridinbasen und aus ebensoviel aliphatischen Nitrilen besteht.The same catalyst composition provides at reduced by half flow rate of the gas mixture under otherwise identical conditions the product, which consists of about 50 'to and from pyridine bases as much aliphatic nitriles.

Beispiel 3 Ein Gemisch aus gleichen Raumteilen Acetaldehyddampf und Ammoniak wird bei 35o° mit einer Geschwindigkeit von Zoo 1 je Stunde und Liter Kontaktmasse über die im Beispiel 2 angewandte Köntaktmasse geleitet. Es findet eine fast völlige Umsetzung des Aldehyds zu stickstoffhaltigen Kondensationsprodukten statt, die über go "/o Pyridinbasen enthalten.Example 3 A mixture of equal parts by volume of acetaldehyde vapor and Ammonia is at 35o ° at a rate of zoo 1 per hour and liter of contact mass passed over the contact mass used in Example 2. It finds an almost utter one Implementation of the aldehyde to nitrogen-containing condensation products instead, which over go "/ o contain pyridine bases.

Beispiel 4 Über mit Thoriumoxyd beladenes Kieselsä Uregel werden bei 35o° 30 1 Ammoniak und je 15 1 Acetaldehyd und Wasserdampf je Stunde und Liter Kontaktmasse geleitet. Das erhaltene Kondensat enthält neben Wasser stickstoffhaltige Kondensationsprodukte in einer Ausbeute von über cgo °/o der Theorie, berechnet auf den angewandten Aldehyd. go Volumprozent davon sind Pyridinbasen, der Rest besteht aus Nitrilen und geringen Mengen von Ammoniumcyanid.Example 4 About silica loaded with thorium oxide are used in 35o ° 30 1 ammonia and 15 1 acetaldehyde and water vapor per hour and liter of contact mass directed. In addition to water, the condensate obtained contains nitrogen-containing condensation products in a yield of over cgo% of theory, calculated on the aldehyde used. go percent by volume of it are pyridine bases, the remainder consists of nitriles and small ones Amounts of ammonium cyanide.

Beispiel 5 Ein Gemisch aus je drei Teilen Acetylen und Ammoniak und je einem Teil Acetaldehyd und Wasserdampf, .das mit einer Geschwindigkeit von etwa ioo 1 je Stunde und Liter Kontaktmasse bei 34o° über auf Kieselsäuregel verteiltes Alumniumoxyd und Cadmiummetall geleitet wird, liefert je Kubikmeter Gasgemisch etwa 4oo ccm eines aus zwei Schichten bestehenden Kondensates, dessen obere Schicht (etwa goojo der Gesamtflüssigkeit) zu über 75 ojo aus Pyridinbasen, vorwiegend Picolinen, besteht.Example 5 A mixture of three parts each of acetylene and ammonia and one part each acetaldehyde and water vapor, .at a speed of about 100 1 per hour and liter of contact mass at 34o ° over distributed silica gel Alumnium oxide and cadmium metal is conducted, delivers approximately per cubic meter of gas mixture 400 ccm of a condensate consisting of two layers, the upper layer of which (approx goojo of the total liquid) to over 75 ojo from pyridine bases, mainly picolines, consists.

Beispiel 6 Ein Gemisch von je zwei Teilen Acetaldehyd- und Propionaldehyddampf mit vier Teilen Ammoniak wird mit einer Geschwindigkeit von 5o l je Stunde und Liter Kontaktmasse über mit Zinkoxyd und Thoroxyd beladenes Kieselsäuregel bei 38o° geleitet. Man erhält je Liter flüssiges Aldehydgemisch etwa q.50 ccm Öle, die zu etwa 35"/" aus Picolin und zu etwa so 01, aus höheren Basen, insbesondere Kollidin, bestehen.Example 6 A mixture of two parts each of acetaldehyde and propionaldehyde vapor with four parts of ammonia is produced at a rate of 50 liters per hour and liter Contact mass passed over silica gel loaded with zinc oxide and thoroxide at 38o °. About 50 cc of oils are obtained per liter of liquid aldehyde mixture, which make up about 35 "/" from picoline and about so 01, from higher bases, especially collidine.

Beispiel i Kieselsäuregel wird mit einer wässerigen Lösung von zehn Teilen Aluminiumnitrat und einem Teil Zirkoniumnitrat getränkt und einige Zeit lang auf 400° im Luftstrom erhitzt. über diese Kontaktmasse wird bei 36o° je ein Teil Propionaldehyddampf und Ammoniak mit zwei Teilen Wasserstoff mit einer Geschwindigkeit von 151 Ammoniak je Liter Kontaktmasse und Stunde geleitet. Man erhält je Liter flüssigen Propionaldehyd etwa goo ccm Kondensat, dessen Ölschicht nach dem Aussalzen etwa 55o ccm beträgt. Diese Ölschicht besteht aus etwa 25 0J" Nitrilen und 75 0lo Pyridinbasen, von letzteren dei überwiegende Anteil aus Parvolinen (Methyläthylpyridin).Example i Silica gel is made with an aqueous solution of ten Part aluminum nitrate and part zirconium nitrate and soaked for some time heated to 400 ° in a stream of air. A part is placed over this contact mass at 36o ° Propionaldehyde vapor and ammonia with two parts hydrogen at one rate of 151 ammonia per liter of contact mass per hour. You get per liter liquid propionaldehyde about goo ccm condensate, its oil layer after salting out is about 55o cc. This oil layer consists of about 25 0J "nitriles and 75 0lo Pyridine bases, of the latter the predominant part consists of parvolines (methylethylpyridine).

Beispiel 8 .6o ccm roher Valeraldehyd, der neben Wasser einen größeren Prozentsatz Valeriansäure enthält, werden verdampft und die Dämpfe bei 32o° zusammen mit io 1 Ammoniak und 1o i Methan je Liter Kontaktmasse und Stunde über mit Aluminiumoxyd und Cadmium beladenes Kieselsäuregel geleitet. Man erhält ein Kondensat, dessen Ölschicht, etwa G5°;" des Gesanltkoncle»sats, neben höheren Nitrilen, insbesondere Valeronitril, zu etwa 700,r" aus höheren Pyridinbasen. vor- wiegend aus I`ollidinen und Parvolinen, be- stellt. EXAMPLE 8,6o ccm of crude valeraldehyde, which contains a larger percentage of valeric acid in addition to water, is evaporated and the vapors are passed at 32o ° together with 10% ammonia and 10% methane per liter of contact mass per hour over silica gel loaded with aluminum oxide and cadmium. A condensate is obtained, the oil layer of which about G5 °; "of the Gesanltkoncle» sate, next to higher nitriles, especially valeronitrile, to about 700, r "from higher pyridine bases. mainly made of I`ollidinen and Parvolinen, represents.

Claims (1)

PATLNTANSPRÜCHr: r. Verfahren zur Herstellung eines vor- wiegend aus Pyridtnbasen bestellenden Produktes, dadurch ;elcennzeicliliet, daß nian ein Gemisch voll Acetylen, Wasser- dampf und Aninioniak oder ein Gemisch
von Aldehyden, insbesondere Acetaldeli5-d, und Ammoniak vorteilhaft bei Tem- peraturen unterhalb .[oo° mit einer Ge- schwindigkeit Tiber Katalysatoren leitet, die gröl,ter ist als die für die Bildung eines vorwiegend all.,; Nitrilen bestellen- den Produktes 'erforderliche. 2. VC1-f'<tllre1l nach Anspruch i, dadurch geken1lzeichnet, daß der 1Vasserdampf- gellalt cles umzusetzenden Gasgemisches das Ein- bis Zweifache des Acetylengehal- tes beträgt.
PATLNT CLAIMS: r. Process for the production of a pre- predominantly ordering from pyramid bases Product, thereby; elcennzeicliliet that nian a mixture full of acetylene, water steam and anionic acid or a mixture
of aldehydes, especially Acetaldeli5-d, and ammonia advantageous at tem- temperatures below. [oo ° with a speed through catalytic converters, which is bigger, bigger than the one for education one predominantly all.,; Order nitriles- the product 'required. 2. VC1-f '<tllre1l according to claim i, characterized geken1l marked that the 1Vapor gellalt cles the gas mixture to be converted one to two times the acetylene content tes is.
DEI35652D 1928-09-28 1928-09-28 Process for the preparation of pyridine bases Expired DE523602C (en)

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DEI35652D DE523602C (en) 1928-09-28 1928-09-28 Process for the preparation of pyridine bases

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DEI35652D DE523602C (en) 1928-09-28 1928-09-28 Process for the preparation of pyridine bases

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1105871B (en) * 1953-04-22 1961-05-04 Bayer Ag Process for the production of ª ‡ - and ª † -picolin from acetaldehyde and ammonia
DE1289528B (en) * 1959-05-15 1969-02-20 Distillers Co Yeast Ltd Process for the continuous production of ª ‡ - and ª † -picolin
US6937137B1 (en) 1999-05-19 2005-08-30 Robert Bosch Gmbh Method for locking a motor vehicle in a keyless manner

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1105871B (en) * 1953-04-22 1961-05-04 Bayer Ag Process for the production of ª ‡ - and ª † -picolin from acetaldehyde and ammonia
DE1289528B (en) * 1959-05-15 1969-02-20 Distillers Co Yeast Ltd Process for the continuous production of ª ‡ - and ª † -picolin
US6937137B1 (en) 1999-05-19 2005-08-30 Robert Bosch Gmbh Method for locking a motor vehicle in a keyless manner

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