DE1967047C3 - Verfahren zur Herstellung von Bipyridylen - Google Patents

Verfahren zur Herstellung von Bipyridylen

Info

Publication number
DE1967047C3
DE1967047C3 DE1967047A DE1967047A DE1967047C3 DE 1967047 C3 DE1967047 C3 DE 1967047C3 DE 1967047 A DE1967047 A DE 1967047A DE 1967047 A DE1967047 A DE 1967047A DE 1967047 C3 DE1967047 C3 DE 1967047C3
Authority
DE
Germany
Prior art keywords
bipyridyls
pyridyl
pyridine
group
general formula
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
DE1967047A
Other languages
English (en)
Other versions
DE1967047B2 (de
DE1967047A1 (de
Inventor
R D Bowden
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of DE1967047A1 publication Critical patent/DE1967047A1/de
Publication of DE1967047B2 publication Critical patent/DE1967047B2/de
Application granted granted Critical
Publication of DE1967047C3 publication Critical patent/DE1967047C3/de
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
    • C07D213/22—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 containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/51—Acetal radicals
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides

Landscapes

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

Description

Es ist bekannt. Bipyridyle aus Pyridin selbst durch Umsetzung eines Pyridins mit einem Metall und Oxidation des so erhaltenen Zwischenprodukts herzustellen. So ist beispielsweise in der DE-OS 14 45 944 ein Verfahren zur Herstellung von 4,4'-Bipyridyl durch Umsetzung von Pyridin mit Natrium beschrieben. Die vorliegende Erfindung schafft dagegen ein Verfahren lur Herstellung von Bipyridylen aus Ausgangsmateria-Ken, die selbst aus den entsprechenden Methylpyridinen, im Unterschied zu Pyridin selbst, hergestellt werden können.
Gegenstand der Erfindung ist somit ein Verfahren zur Herstellung von Bipyridylen, welches dadurch ausgeführt wird, daß man ein entsprechendes Piperidyl-pyridin oder ein substituiertes Pyridin, wobei der Substituent die allgemeine Formel
-CHXY
aufweist, in der X eine Gruppe der allgemeinen Formel
-CH2-CH,-NR.R,
ist, wobei Ri und R.> jeweils ein Wasserstoffatom oder eine Alkylgruppe bedeuten, und Y die gleiche ledeutung wie X hat oder eine Gruppe der allgemeinen Formel
dadurch verdampft werden, daß es auf die erforderliche Temperatur erhitzt wird. Eine besonders geeignete Technik besteht darin, das Material in Form eines Stroms aus feinen Tröpfchen auf eine heiße Oberfläche fallen zu lassen, wie z. B. auf einen Verdampfer oder auf den Aluminiumoxidkatalysator. Das Material kann in zweckmäßiger Weise in einem Verdampfer verdampft werden, bevor es mit dem Katalysator in Berührung kommt Einige der Ausgangsmaterialien sind jedoch bei
ίο gewöhnlichen Temperaturen klebrige, viskose Flüssigkeiten oder Feststoffe. Diese werden vor der Verdampfung in zweckmäßiger Weise in einem geeigneten Lösungsmittel aufgelöst Beispiele für geeignete Lösungsmittel für diesen Zweck sind Wasser und Alkohole, insbesondere niedrige aliphatische Alkohole und insbesondere Methanol.
Die durch das Verfahren gebildete-, Bipyridyle können durch bekannte Techniken von den Reaktionsprodukten isoliert werden. Beispielsweise können die gasförmigen Reaktionsprodukte kondensiert werden, und das Bipyndyl kann dann aus dem Kondensat durch Lösungsmittelextraktion und/oder fraktionierte Destillation, ggf. unter vermindertem Druck, isoliert werden. Wenn Wasser im Reaktionsprodukt anwesend ist, das bei der Herstellung von 4,4'-Bipyridylen erhalten wird, dann können diese Bipyridyle durch Filtration abgetrennt werden.
Das Verfahren kann absatzweise durchgeführt werden, aber es besitzt den Vortei1, daß es in einer
jo kontinuierlichen Arbeitsweise betrieben werden kann.
Das Verfahren eignet sich besonders für die Herstellung von 4,4'·Bipyridylen, obwohl andere Isomere wie z. B. 2,2'-, 2,4'-. 23'- und 3,4'-Bipyridyle durch eine geeignete Auswahl des Ausgangsmaterials ebenfalls erhalten werden können.
Die Erfindung wird durch die folgenden Beispiele näher erläutert:
ist, wobei Z ein Wässerstöffalörri, eme Alkyl· öder Hydroxyäthylgruppe und η I oder 2 bedeuten,"mit molekularem Sauerstoff in öegeriwart von Ammoniak in der Dampfphase bei einer Temperatur im Bereich Von mehr als 250 bis 450°C, vorzugsweise 35Ö bis 450"C, über einem AlUminiufnöxidkatälysatör umsetzt
Das Äusgangsmaterial kann in einfacher Weise Beispiele 1 bis 8
Das Verfahren war in jedem Beispiel wie folgt:
Ein Katalysatorbett wurde aus einer pelletisieren
4> Form des Aluminiumoxidkatalysators bis zu einer bestimmten Tiefe in einem vertikalen Glasreaktionsrohr mit einem Innendurchmesser von 25 mm hergestellt. Das Rohr war mit einer zentralen Thermoelemenitasche ausgerüstet und enthielt überd «n Katalysatorbett
in Raschig-Ringe. Die Raschig-Ringe füllten das Rohr ircht vollständig. Das Rohr war in einem vertikalen Ofen angeordnet, der auf der entsprechenden Temperatur gehalten wurde.
Das substituierte Pvridin wurde in Wasser oder Methanol aufgelöst, und die Lösung wurde zur Oberseite des Reaktionsrohrs geführt, wo sie beim Kontakt mit den Raschig-Ringen verdampfte. Die Dämpfe wurden nach unten durch das Katalysatorbett geführt. Die Dämpfe wurden mit Sauerstoff und
fen Ammoniak, wie m der Tabelle angegeben, für den Durchgang durch das Katalysatorbett gemischt lri einigen Fällen Wurde das Mischen j'ectöch unterhalb der Oberfläche des Katalysatorbetts ausgeführt
Der Abstroffl aus dem Reaktor wurde kondensiert,
bi Und das Kondensat wurden sofern es flüssig war (was für die meisten Experimente gilt), durch Gas/Flüssigkeits-Chromatografie analysiert, wobei Standardtechniken verwendet wurden. Wenn das Kondensat ein Feststoff
3
war, dann wurde dieser in Methanol aufgelöst, worauf In der Tabelle gelter, folgende Abkürzungen:
die Lösung analysiert wurde, . _ _
In der Tabelle ist der Katalysator durch den nh?nge« - Unge des Katalysatorbett«
RiiPhinhen A bezeichnet- »Temp.« = Temperatur des Katalysatorbetts
Buchstaben A bezeichnet. >>Verd<< _ g Ausgangsmateria|/m, iÄung5mjtte|
A. Pellets von 3x3 mm aus Aluminiumoxid. »MeOH« = Methanol.
Bei- Substituiertes spiel Pyridin
Katalysator
Kata- Länge Temp, lysator
(mm) ( C)
Flüssigkeitsbeschickung Gasbeschickung
Zeit Verd. Lösungs- Luft N2 NHj
(min)
mittel
(ml/
min)
(ml/
min)
(ml/
min)
Umwandlung in 4,4'-Bipyridyl
1 3-{4'-Pyridyl)- A 76 360-420 51 1,3/20 MeOH 100
l,l-diäthoxy-5-
dimethylamino- A 76 350-390 100 2,6/50 H2O/ 100
pe?itan MeOH
2 6-(4'-Pyt-£iyl)- (2: 1)
8-dimethylamino- A 76 330-360 50 4,5/30 MeOH too
3-oxaoctan-I-ol
3 3-(4'-Pyridyl)-
5-dimethylamino- A 76 320-340 47 2,4/25 MeOH IK)
pentan-1-ol
A 3-(4'-Pyridyl)-
1,5-bis-dimethyI- A 76 330-363 70 4,7/18 MeOH !00
aminopentan
S 3-(4'-Pyridyl)-
5-diäthylaii ino- A 76 320-380 60 3,3/30 MeOH 100
pentan-1-ol
6 3-{4'-Pyridyl)-
1,5-bis-diäthyl- A 76 340-405 70 2,08/25 MeOH 100
aminopentan
7 4-{4'-Pyridyl)- A 76 337-401 52 1,9/25 H2O/ 100
pipcridin MeOH
I 2-(3'-Pyridyl)-
piperidin
(Anabasin)
830 57
830 72
830 41
830 39
830 36
830 34
830 89
.330 2,3'-Bi-
pyridyl 72
In der obigen Tabelle sind die angegebenen Produkte die Hauptprodukte. In vielen Beispielen wurden jedoch auch andere Produkte identifiziert wie folgt:
Beispiel Andere Produkte Nr.
3 4-(4'-Pyridyl)tetrahydropyran (19%) und N-Methyl-4-(4'-pyridyl)piperidin
4 N'-Methyl-4-(4'-pyridyl)piperidin
5 4-(4'-Pyridyl)tetrahydropyran und N-Äthyl-4-(4'-pyridyl)piperidin
6 N*Äthyl-4"(4'-pyridyl)piperidin
8 2'-oder 3-Methyl-2,3'-bipyridyl und 5-Methyl-2,3'-bipyridil

Claims (1)

  1. Patentanspruch:
    Verfahren zur Herstellung von Bipyridylen, dadurch gekennzeichnet, daß man ein entsprechendes Piperidyl-pyridin oder ein substituiertes Pyridin, wobei der Substituent die allgemeine Formel
    -CHXY
    aufweist, in der X eine Gruppe der allgemeinen Formel
    -CH2-CH2-NR1R2
    ist, wobei Ri und R2 jeweils ein Wasserstoffatom oder eine Alkylgruppe bedeuten, und Y die gleiche Bedeutung wie X hat oder eine Gruppe der allgemeinen Formel
    ist, wobei Z ein Wasserstoffatom, eine Alkyl- oder Hydroxyäthylgruppe und η 1 oder 2 bedeuten, mit molekularem Sauerstoff in Gegenwart von Ammoniak in der Dampfphase bei einer Temperatur im Bereich von mehr als 250 bis 450° C über einem Aluminiumoxidkatalysator umsetzt
DE1967047A 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen Expired DE1967047C3 (de)

Applications Claiming Priority (11)

Application Number Priority Date Filing Date Title
GB46736/71A GB1268194A (en) 1968-03-18 1968-03-18 Pyridine derivatives and their manufacture
GB1300868 1968-03-18
GB46739/71A GB1268196A (en) 1968-03-18 1968-05-29 Pyridine derivatives and their manufacture
GB2577368 1968-05-29
GB6071468 1968-12-20
GB6071568 1968-12-20
GB6071668 1968-12-20
GB4673771 1968-12-20
GB246/69A GB1268191A (en) 1968-03-18 1969-01-02 Process for the manufacture of bipyridyls
US17417571A 1971-08-23 1971-08-23
US412093A US3873555A (en) 1968-03-18 1973-11-02 Process for the manufacture of bipyridyls

Publications (3)

Publication Number Publication Date
DE1967047A1 DE1967047A1 (de) 1976-10-07
DE1967047B2 DE1967047B2 (de) 1980-05-14
DE1967047C3 true DE1967047C3 (de) 1981-01-22

Family

ID=27581625

Family Applications (4)

Application Number Title Priority Date Filing Date
DE1913732A Expired DE1913732C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE19691967049 Withdrawn DE1967049A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen
DE1967047A Expired DE1967047C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE19691967048 Withdrawn DE1967048A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

Family Applications Before (2)

Application Number Title Priority Date Filing Date
DE1913732A Expired DE1913732C3 (de) 1968-03-18 1969-03-18 Verfahren zur Herstellung von Bipyridylen
DE19691967049 Withdrawn DE1967049A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

Family Applications After (1)

Application Number Title Priority Date Filing Date
DE19691967048 Withdrawn DE1967048A1 (de) 1968-03-18 1969-03-18 Verfahren zur herstellung von 4-(pyridyl)-tetrahydropyranen

Country Status (9)

Country Link
US (2) US3651071A (de)
AT (5) AT292705B (de)
BE (1) BE729987A (de)
CH (6) CH538506A (de)
DE (4) DE1913732C3 (de)
FR (1) FR2004163A1 (de)
GB (4) GB1268194A (de)
NL (1) NL167689C (de)
SE (2) SE392468B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2022886A1 (en) * 1989-08-08 1991-02-09 Raymond Baker Substituted pyridines, their preparation, formulations and use in dementia
DE19536652A1 (de) * 1995-09-30 1997-04-10 Judit Kirschke Kompresse zur Wärmetherapie unter Verwendung von temperaturregulierendem und/oder heilendem und/oder beschwerdelinderndem Material
JP4603646B2 (ja) * 1999-11-15 2010-12-22 富士フイルムファインケミカルズ株式会社 新規なジピリジル誘導体
WO2005082872A1 (ja) * 2004-03-02 2005-09-09 Dainippon Sumitomo Pharma Co., Ltd. ベンゾチアジン－３－オン化合物及びその製造中間体
JP5235947B2 (ja) * 2010-07-30 2013-07-10 富士フイルムファインケミカルズ株式会社 新規なジピリジル誘導体

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL131727C (de) * 1963-08-08 1900-01-01

Also Published As

Publication number Publication date
AT292705B (de) 1971-09-10
DE1913732C3 (de) 1982-04-15
GB1268194A (en) 1972-03-22
GB1268191A (en) 1972-03-22
FR2004163A1 (de) 1969-11-21
NL6903976A (de) 1969-09-22
DE1967047B2 (de) 1980-05-14
DE1913732A1 (de) 1970-02-19
NL167689B (nl) 1981-08-17
SE394111B (sv) 1977-06-06
CH530997A (de) 1972-11-30
DE1967048A1 (de) 1976-11-04
AT292706B (de) 1971-09-10
CH540910A (de) 1973-10-15
AT295535B (de) 1972-01-10
NL167689C (nl) 1982-01-18
DE1913732B2 (de) 1981-04-02
CH540255A (de) 1973-10-15
CH532051A (de) 1972-12-31
US3873555A (en) 1975-03-25
BE729987A (de) 1969-09-17
DE1967049A1 (de) 1976-11-04
CH542222A (de) 1973-11-15
US3651071A (en) 1972-03-21
AT292704B (de) 1971-09-10
CH538506A (de) 1973-08-15
GB1268196A (en) 1972-03-22
GB1268195A (en) 1972-03-22
DE1967047A1 (de) 1976-10-07
AT289797B (de) 1971-05-10
SE392468B (sv) 1977-03-28

Similar Documents

Publication Publication Date Title
DE197308C (de)
DE1967047C3 (de) Verfahren zur Herstellung von Bipyridylen
DE602005001941T2 (de) Katalytische dampfphasenchlorierung von beta-picolin
CH617679A5 (de)
DE2351947C3 (de) Verfahren zur Herstellung von tetrachlorierten Phthalsäuredinitrilen
DE1545984B1 (de) Verfahren zur Herstellung von Pentachlorpyridin
DE1470143A1 (de) Verfahren zur Herstellung von 2-Chlorpyridin
DE1958595C3 (de) Verfahren zur Herstellung total chlorierter aromatischer oder hetero aromatischer Mono , Di oder Trinitnle Anτi Diamond Shamrock Corp , Cleveland, Ohio (V St A )
DE1443096C3 (de) Verfahren zur Herstellung von Naphthalin aus Alkylnaphthallne enthaltenden Kohlenwasserstoffen
AT289802B (de) Verfahren zur Herstellung von Bipyridylen
DE1420094C (de) Fraktionierverfahren zur destillativen Abtrennung von 2 Methyl 5 vinylpyridin aus einem im wesentlichen aus 2 Methyl 5 vinyl pyridin und 2 Methyl 5 athylpyridin be stehenden Gemisch
DE1150997B (de) Verfahren zur Herstellung von aschefreien Pechen
DE1470142C (de) Verfahren zur gleichzeitigen Herstel lung von 2 Brom und 2 Chlorpyndin
DE1445683B2 (de) Verfahren zur Herstellung von Poly chlorpyndinen
DE237524C (de)
AT277182B (de) Verfahren zur Herstellung von 1,2-Dichloräthan
DE1695229C3 (de) Verfahren zur Substitution von Chloratomen durch Fluoratome in Difluor tnchlor bzw Tnfluor dichlorpyndinen
DE1545570C3 (de) Verfahren zur Herstellung von Dichlorpyrazinen
DE852244C (de) Verfahren zur Gewinnung von Pyridin und Pyridincarbonsaeuren
DE1445918C (de) Verfahren zur Herstellung von gegebenenfalls durch eine oder mehrere niedermolekulare Alkylgruppen substituierten Bipyridylen
DE540971C (de) Verfahren zur Herstellung eines resenarmen Harzes aus Harzbalsam (Gemme)
DE1068693B (de)
DD241590A1 (de) Verfahren zur essigsaeuregewinnung aus dem reaktionsgasstrom der acetaldehydsynthese
AT235301B (de) Verfahren zur Herstellung von Melamin
AT102540B (de) Verfahren zur Gewinnung der in Rückständen enthaltenen nützlichen Produkte durch heiße Destillation.

Legal Events

Date Code Title Description
C3 Grant after two publication steps (3rd publication)
8339 Ceased/non-payment of the annual fee