DE743469C - Process for the preparation of pyridines in addition to nitriles, etc. - Google Patents

Process for the preparation of pyridines in addition to nitriles, etc.

Info

Publication number
DE743469C
DE743469C DEI70406D DEI0070406D DE743469C DE 743469 C DE743469 C DE 743469C DE I70406 D DEI70406 D DE I70406D DE I0070406 D DEI0070406 D DE I0070406D DE 743469 C DE743469 C DE 743469C
Authority
DE
Germany
Prior art keywords
addition
nitriles
pyridines
preparation
allyl
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
DEI70406D
Other languages
German (de)
Inventor
Dr Walter Franke
Dr Wolfgang Thiele
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI70406D priority Critical patent/DE743469C/en
Application granted granted Critical
Publication of DE743469C publication Critical patent/DE743469C/en
Expired legal-status Critical Current

Links

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
    • C07D213/06—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

Landscapes

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

Description

Verfahren zur Herstellung von Pyridinen neben Nitrilen usw. Gegenstand des Patents 7q.0-638 isst ein Verfahren zwr Herstellung von Pyridinen neben Nitrilen, bei dem man u. a. - auf ge-; tti-te i, 4-Diole in der Gasphase bei ers äu g höhter Temperatur Cyaiiwasserstoff in Anwesenheit von Füllkörpern oder großob@erflä chigen Stoffen ei wirken läßt. Ein Teil der i, 4-Diole kann dabei unter Abspaltung eines Moleküls. Wasser in Allylcarbnole Übergehcn.Process for the production of pyridines in addition to nitriles, etc. The subject of the patent 7q.0-638 is a process for the production of pyridines in addition to nitriles, in which one inter alia - on ge; i-th TTI 4-diols in the gas phase at elevated temperature ers externa g Cyaiiwasserstoff in the presence of packings or can großob @ erflä speaking substances ei act. Some of the 1,4-diols can thereby split off a molecule. Water converts into allyl carbnols.

Es wurde nun gefunden, daß man Allylcarbinole, die dairch Wasserabspaltung aus i, 4-Diolen erhältlich sind, ebenfalls in Pyridine neben Nitrilen überführen kann, uaenn man sie in der Gasphase bei erhöhter Temperatur mit Cyan«,asserstoff umsetzt. Die Umsetzungsbedingungen sind dabei grundsätzlich die gleichen wie heim Verfahren des Hauptpatents. Beispiel-In ein senkrechtes, ' ,eisernes Rohr von i m Länge und 4 cm Durchmesser, das 7u drei Vierteln mit dem in der Patentschrift 664 817, Beispiel 3, beschriebenen alaiven Aluminiumoxyd und itn oberen Viertel mit Glasringen gefüllt ist, läßt man bei 455° im Laufe von 8 Stunden ein Gemisch aus ioo,8 g Allylcarbinol und 2z6,8 g Cyamvasserstoff (Molverh:ältnis i:6) tropfen. Die Umsetzungsgase «-erden durch Binse luftgekühlte Vorlage einen mit 2ooroiger Schwefelsäure berieselten Waschturm geleitet, an den sich eine auf o° und eine auf -8o° gekühlte Vorlage anschließen. Nach Beendigung der Umsetzung enthält die erste Vorlage 43 g, die SchWefelsäure hat 93 g aufgenommen, die auf o° gekühlte Vorlage enthält 48g und die Tiefkühlvorlage taog (großenteils Butadien). lach dem Abdestillieren des Butadiens wird der Inhalt aller Vorlagen vereinigt und bei saurer Reaktion mit Äther extrahiert. Aus der Ätherlösung erhält man bei der Destillation neben nicht umgesetztem Allylcarbinol i2,8 g Allylessigsäurenitril sowie 7, i g höhere neutrale, stickstoffhaltige Verbindungen. Die beim Ausäthern zurückbleibende saure Lösung wird mit konzentrierter Alkalilauge im Überschoß versetzt und ebenfalls mit Äther extrahiert. Bei der Destillation der ätherischen Lösung erhält man etwa gleiche Mengen von Pyridin und höher siedenden Basen.It has now been found that allyl carbinols, which are obtainable from 1,4-diols for dehydration, can also be converted into pyridines in addition to nitriles, inter alia if they are reacted with cyano hydrogen in the gas phase at elevated temperature. The implementation conditions are basically the same as in the procedure for the main patent. Example-In a vertical, ', iron tube 1 m in length and 4 cm in diameter, which is three quarters filled with the alaive aluminum oxide described in the patent specification 664 817, Example 3, and in the upper quarter with glass rings, is left at 455 ° a mixture of 100.8 g of allyl carbinol and 26.8 g of hydrogen cyanide (molar ratio: 6) was added dropwise over the course of 8 hours. The reaction gases "earth" through rushes air-cooled receiver to a washing tower sprinkled with 2ooroiger sulfuric acid, followed by a receiver cooled to 0 ° and a receiver cooled to -80 °. When the reaction is complete, the first receiver contains 43 g, the sulfuric acid has taken up 93 g, the receiver cooled to 0 ° contains 48 g and the frozen receiver contains taog (mostly butadiene). After the butadiene has been distilled off, the contents of all templates are combined and, if the reaction is acidic, extracted with ether. In the distillation of the ether solution, in addition to unconverted allyl carbinol, 2.8 g of allyl acetic acid nitrile and 7% higher neutral, nitrogen-containing compounds are obtained. The acidic solution remaining after the etherification is mixed with an excess of concentrated alkali and also extracted with ether. When the ethereal solution is distilled, roughly equal amounts of pyridine and higher-boiling bases are obtained.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Pyridin neben Nitrilen usw.. dadurch gekennzeichnet, daß man in Weiterbildung des Verfahrens nach Patent ,^q.o 638 hier auf Allylcarbinole in der Gasphase bei erhöhter Temperatur Cyanwasserstoff in Anwesenheit von Füllkörpern oder großoberflächigen Körpern einwirken läßt. Zur Abgrenzung des Anmeldungsgegenstandes vom Stand der Technik ist im Erteilungsverfahren keine Druckschrift in Betracht gezogen worden.PATENT CLAIM: Process for the production of pyridine in addition to nitriles etc .. characterized in that in further development of the method according to patent , ^ q.o 638 here on allyl carbinols in the gas phase at elevated temperature hydrogen cyanide can act in the presence of packing or large-surface bodies. To the The subject of the application is differentiated from the state of the art in the granting procedure no pamphlet has been considered.
DEI70406D 1941-09-06 1941-09-06 Process for the preparation of pyridines in addition to nitriles, etc. Expired DE743469C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI70406D DE743469C (en) 1941-09-06 1941-09-06 Process for the preparation of pyridines in addition to nitriles, etc.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI70406D DE743469C (en) 1941-09-06 1941-09-06 Process for the preparation of pyridines in addition to nitriles, etc.

Publications (1)

Publication Number Publication Date
DE743469C true DE743469C (en) 1943-12-27

Family

ID=7197096

Family Applications (1)

Application Number Title Priority Date Filing Date
DEI70406D Expired DE743469C (en) 1941-09-06 1941-09-06 Process for the preparation of pyridines in addition to nitriles, etc.

Country Status (1)

Country Link
DE (1) DE743469C (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

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