CH513094A - Procédé pour la préparation d'alcools non saturés - Google Patents

Procédé pour la préparation d'alcools non saturés

Info

Publication number
CH513094A
CH513094A CH1805370A CH1805370A CH513094A CH 513094 A CH513094 A CH 513094A CH 1805370 A CH1805370 A CH 1805370A CH 1805370 A CH1805370 A CH 1805370A CH 513094 A CH513094 A CH 513094A
Authority
CH
Switzerland
Prior art keywords
formula
lower alkyl
alkyl radical
ketones
unsaturated cycloaliphatic
Prior art date
Application number
CH1805370A
Other languages
English (en)
Inventor
Ervin Dr Kovats
Edouard Dr Demole
Guenther Dr Ohloff
Max Dr Stoll
Original Assignee
Firmenich & Cie
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 Firmenich & Cie filed Critical Firmenich & Cie
Priority to CH1805370A priority Critical patent/CH513094A/fr
Publication of CH513094A publication Critical patent/CH513094A/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
    • A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
    • A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
    • C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/04—Acyclic alcohols with carbon-to-carbon triple bonds
    • C07C33/048—Acyclic alcohols with carbon-to-carbon triple bonds with double and triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
    • C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Seasonings (AREA)
  • Epoxy Compounds (AREA)

Description


  
 



  Procédé pour la préparation d'alcools non saturés
 La présente invention a pour objet un procédé pour la préparation d'alcools non saturés de formule:
EMI1.1     
 dans laquelle R représente l'hydrogène ou un reste alcoyle.



   Les alcools I sont d'une grande utilité en tant qu'intermédiaires pour la fabrication des cétones correspondantes de formule:
EMI1.2     
 par oxydation de la fonction hydroxyle. Lesdites cétones sont des produits doués de remarquables propriétés organoleptiques et intéressent l'industrie des parfums et des arômes.



   Le procédé suivant l'invention est caractérisé en ce qu'on isomérise et simultanément réduit un époxyde de la   oy-ionone    de formule:
EMI1.3     
 au moyen d'un agent simultanément isomérisant et réducteur.



   Comme tel agent, on peut utiliser l'hydrate d'hydrazine suivant un procédé décrit dans Tetrahedron 19, 1091 (1963) et J. Org. Chem. 26, 3615 (1961).



   L'époxyde de la y-ionone, lequel existe sous 2 formes isomères, peut être préparé par époxydation de la   y-io-    none suivant une méthode décrite dans la première des références ci-dessus.



   L'exemple qui suit illustre   Invention    de manière plus détaillée. Les températures y sont données en degrés centigrades.



   Exemple
 Préparation de   6,6-diméthyl-1 -(1 -hydroxy-2-butényi)-2-   
 méthylènecyclohexane
 a) Sous protection d'azote, on a ajouté goutte à goutte, à 00, 5 g d'époxyde A, préparé selon la méthode décrite au paragraphe b) ci-dessous, dissous dans 5 ml de méthanol à une solution de   10ml    d'hydrate d'hydrazine pur dans 5 ml de méthanol. L'addition a requis 1 1/2 h.

  On a agité encore 2 h, puis on a procédé au traitement habituel et on a obtenu, avec un rendement de   360/0,    un distillat contenant le 6,6-diméthyl-1-[1-hy   droxy-butén-(2)-yl-( 1)] -2-méthylènecyclohexane,    cis-, isomère A (8   O/o),    la forme trans- du même alcool, isomère
A (7   O/o)    et le   2,2,6,7-tétraméthylbicyclo-[4.3.0]-nonén-    (7)-ol(9), isomère A   (80 0/0).    Ces trois corps ont été séparés par chromatographie préparative en phase gazeuse.



   En procédant de même que ci-dessus avec l'époxyde
B, préparé selon la méthode décrite au paragraphe b) ci-dessous, on a obtenu le 6,6-diméthyl-1-[1-hydroxy   butén-(2)-yl-(1)] -2-méthylènecyclohexane,    cis-, isomère
B   (36 0/o),    la forme trans- du même alcool, isomère B (58   O/o)    et le   2,2,6,7-tétraméthylbicyclo-[4.3.0]-nonén-(7)-    ol-(9), isomère B (2   O/o).     



   Les produits de départ utilisés dans la préparation décrite ci-dessus peuvent être obtenus ainsi:
 b) A une solution de 50 g de y-ionone dans 3 litres de   MzOH    on a ajouté 120 ml de   H.,O2    à   30 oxo    et 30   ml    de NaOH 6 N. On a agité 24 h à température ambiante, rajouté   50ml    de   H2O.2à      30 /o    et poursuivi l'agitation pendant 24 heures. On a répété l'adjonction   d'H2O2    et, après un total de 3 jours consécutifs d'agitation, on a concentré sous vide et soumis le résidu au traitement habituel. 

  On a obtenu, après distillation, 46 g d'un mélange   55 : 45    de 2 époxydes isomères de la y-ionone (époxydes A et B) qu'on a séparés par distillation dans un appareil de distillation à bande tournante ou par chromatographie en phase gazeuse (Carbowax 20 M).



   Epoxyde A, Eb.   88-890/0,1    Torr;   n2D0= 1,4890;      d24       =   0,9972.



   Epoxyde B, Eb.   90-91 /0,1    Torr; F. 43-440.

Claims (1)

  1. REVENDICATION
    Procédé pour la préparation d'alcools non saturés de formule: EMI2.1 dans laquelle R représente l'hydrogène ou un reste alcoyle, caractérisé en ce qu'on isomérise et simultanément réduit un époxyde de la y-ionone de formule: EMI2.2 au moyen d'un agent isomérisant et simultanément réducteur.
    SOUS-REVENDICATION Procédé suivant la revendication, caractérisé en ce qu'on utilise l'hydrate d'hydrazine comme agent isomérisant et simultanément réducteur.
CH1805370A 1969-05-07 1969-05-07 Procédé pour la préparation d'alcools non saturés CH513094A (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CH1805370A CH513094A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation d'alcools non saturés

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1805370A CH513094A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation d'alcools non saturés
CH697669A CH520767A (fr) 1969-05-07 1969-05-07 Utilisation de composés cyclooléfiniques carbonylés comme agents odoriférants

Publications (1)

Publication Number Publication Date
CH513094A true CH513094A (fr) 1971-09-30

Family

ID=4317983

Family Applications (8)

Application Number Title Priority Date Filing Date
CH1804970A CH528225A (fr) 1969-05-07 1969-05-07 Utilisation de composés cyclooléfiniques carbonylés comme agents aromatisants
CH697669A CH520767A (fr) 1967-11-09 1969-05-07 Utilisation de composés cyclooléfiniques carbonylés comme agents odoriférants
CH1805470A CH521298A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de cétones non saturées et leur utilisation comme agents odoriférants
CH1805070A CH521099A (fr) 1969-05-07 1969-05-07 Composition aromatisante
CH1805370A CH513094A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation d'alcools non saturés
CH1805270A CH513097A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de composés cyclooléfiniques carbonylés
CH1805170A CH513096A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de composés cyclooléfiniques carbonylés
CH1805570A CH513098A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de composés cyclooléfiniques carbonylés

Family Applications Before (4)

Application Number Title Priority Date Filing Date
CH1804970A CH528225A (fr) 1969-05-07 1969-05-07 Utilisation de composés cyclooléfiniques carbonylés comme agents aromatisants
CH697669A CH520767A (fr) 1967-11-09 1969-05-07 Utilisation de composés cyclooléfiniques carbonylés comme agents odoriférants
CH1805470A CH521298A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de cétones non saturées et leur utilisation comme agents odoriférants
CH1805070A CH521099A (fr) 1969-05-07 1969-05-07 Composition aromatisante

Family Applications After (3)

Application Number Title Priority Date Filing Date
CH1805270A CH513097A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de composés cyclooléfiniques carbonylés
CH1805170A CH513096A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de composés cyclooléfiniques carbonylés
CH1805570A CH513098A (fr) 1969-05-07 1969-05-07 Procédé pour la préparation de composés cyclooléfiniques carbonylés

Country Status (1)

Country Link
CH (8) CH528225A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2546515B1 (fr) * 1983-05-27 1986-03-28 Rhone Poulenc Sante Procede de preparation de composes carbonyles adpdiethytleniques
DE69504117T2 (de) * 1994-04-08 1999-01-28 Firmenich S.A., Genf/Geneve Cyclische Ketone und deren Verwendung als Riechstoffe

Also Published As

Publication number Publication date
CH521099A (fr) 1972-04-15
CH520767A (fr) 1972-03-31
CH513098A (fr) 1971-09-30
CH513096A (fr) 1971-09-30
CH521298A (fr) 1972-04-15
CH528225A (fr) 1972-09-30
CH513097A (fr) 1971-09-30

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