DE1967047B2 - Verfahren zur Herstellung von Bipyridylen - Google Patents

Verfahren zur Herstellung von Bipyridylen

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Publication number
DE1967047B2
DE1967047B2 DE1967047A DE1967047A DE1967047B2 DE 1967047 B2 DE1967047 B2 DE 1967047B2 DE 1967047 A DE1967047 A DE 1967047A DE 1967047 A DE1967047 A DE 1967047A DE 1967047 B2 DE1967047 B2 DE 1967047B2
Authority
DE
Germany
Prior art keywords
pyridyl
bipyridyls
group
general formula
pyridine
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.)
Granted
Application number
DE1967047A
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English (en)
Other versions
DE1967047C3 (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

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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
    • C07D213/06—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 zur Herstellung von Bipyridylen aus Ausgangsmaterialien, 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-CH2-NRiR2
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
-CH2-CHn(OZ)3-H
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, vorzugsweise 350 bis 4500C, über einem Aluminiumoxidkatalysator umsetzt.
Das Ausgangsmaterial kann in einfacher Weise
W) 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 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 gebildeten Bipyridyle können durch bekannte Techniken von den Reaktionsprodukten isoliert werden. Beispielsweise können die gasförmigen Reaktionsprodukte kondensiert werden, und das Bipyridyl 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 Vorteil, daß es in einer 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'-, 2,3'- und 3,4'-Bipyridyle durch eine geeignete Auswahl des Ausgangsmaterials ebenfalls erhalten werden können.
Die Erfindung wird durch die folgenden Beispiele näher erläutert:
Beispiele 1 bis 8
Das Verfahren war in jedem Beispiel wie folgt:
Ein Katalysatorbett wurde aus einer pelletisierten 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 Thermoelementtasche ausgerüstet und enthielt über dem Katalysatorbett Raschig-Ringe. Die Raschig-Ringe füllten das Rohr nicht vollständig. Das Rohr war in einem vertikalen Ofen angeordnet, der auf der entsprechenden Temperatur gehalten wurde.
Das substituierte Pyridin 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 Ammoniak, wie in der Tabelle angegeben, für den Durchgang durch das Katalysatorbett gemischt. In einigen Fällen wurde das Mischen jedoch unterhalb der Oberfläche des Katalysatorbetts ausgeführt.
Der Abstrom aus dem Reaktor wurde kondensiert, und das Kondensat wurde, sofern es flüssig war (was für die meisten Experimente gilt), durch Gas/Flüssigkeits-Chromatografie analysiert, wobei Standardtechniken verwendet wurden. Wenn das Kondensat ein Feststoff
19 67 047 3 A. Pellets von 3x3 mm aus Aluminiumoxid. 4 Verd. Lösungs- Luft N2
mittel		 NH3 Umwand Ί Beispiel Andere Produkte und N-Methyl-4-(4'-pyridyl)piperidin 5-Methyl-2,3'-bipyridil
dann wurde dieser in Methanol aufgelöst, worauf (ml/ (ml/ (ml/ lung in
4,4'-Bi-
pyridyl		 I Nr.
war. die Lösung analysiert wurde.
In der Tabelle ist der Katalysator durch den		 min) min) min) (%) 1 3 4-(4'-Pyridyl)tetrahydropyran (19%) 5 4-<4'-Pyridyl)tetrahydropyran und N-Äthyl-4-(4'-pyridyl)piperidin
DlICP In der Tabelle gelten folgende Abkürzungen 1,3/20 MeOH 100 830 1 4 N-Methyl-4-(4'-pyridyl)piperidin 6 N-Äthyl-4-(4'-pyridyl)piperidin
»Länge« = Länge des Katalysatorbetts
»Temp.« = Temperatur des Katalysatorbetts		 57 Ϊ 8 2'-oder 3-Methyl-2,3'-bipyridyl und
Bei
spiel
Nr.
2,6/50 H2O/ 100 830
MeOH 72
1 »Verd.« = g Ausgangsmaterial/ml Lösungsmittel (2:1)
' »MeOH« = Methanol. 4,5/30 MeOH 100 830
Substituiertes Katalysator Flüssigkeitsbeschickung Gasbeschickujig 41
Pyridin Ka(a_ Länge Temp. Zeit
lysator
2 (mm) ("C) (min) 2,4/25 MeOH 100 830
39
3-(4'-Pyridyl)- A 76 360-420 51
3 l,l-diäthoxy-5- 4,7/18 MeOH 100 83Ü
dimethylamino- 36
pentan
4 6-(4'-Pyridyl)- A 76 350-390 100 3,3/30 MeOH 100 830
8-dimethylamino- 34
3-oxaoctan-l-ol
5 3-(4'-PyridyI)- A 76 330-360 50 2,08/25 MeOH 100 830
5-dimethylamino- 89
pentan-1-ol 1,9/25 H2O/ 100 830
6 3-(4'-Pyridyl)- A 76 320-340 47 MeOH 2,3'-Bi-
1,5-bis-dimethyl- pyridyl 72
aminopentan
7 3-<4'-Pyridyl)- A 76 330-363 70 In der obigen Tabelle sind die angegebenen Produkte die Hauptprodukte. In vielen Beispielen wurden jedoch auch
5-diäthylamino- andere Produkte identifiziert wie folgt:
8 pentan-1-ol
3-(4'-Pyridyl)- A 76 320-380 60
1,5-bis-diäthyl-
aminopentan
4-(4'-Pyridyl)- A 76 340-405 70
piperidin
2-(3'-Pyridyl)- A 76 337-401 52
piperidin
(Anabasin)

Claims (1)

10
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
-CH2-CHn(OZ)3-,,
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 4500C über einem Aluminiumoxidkatalysator umsetzt
30
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 true DE1967047B2 (de) 1980-05-14
DE1967047C3 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
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
DE1967047C3 (de) 1981-01-22
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

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