DE2643074A1 - METHOD FOR PRODUCING ALKYL-2-INDAN - Google Patents
METHOD FOR PRODUCING ALKYL-2-INDANInfo
- Publication number
- DE2643074A1 DE2643074A1 DE19762643074 DE2643074A DE2643074A1 DE 2643074 A1 DE2643074 A1 DE 2643074A1 DE 19762643074 DE19762643074 DE 19762643074 DE 2643074 A DE2643074 A DE 2643074A DE 2643074 A1 DE2643074 A1 DE 2643074A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- indanone
- given above
- meaning given
- indane
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/75—Reactions with formaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Description
3 Köln, den 25. August 1976 1533 Cologne, August 25, 1976 153
S.A. Hexachimie, 128/ rue Danton, 925o4 Rueil-Malmaison (Frankreich) SA Hexachimie, 128 / rue Danton, 925o4 Rueil-Malmaison (France)
Die Erfindung betrifft ein Verfahren zur Herstellung von Alkyl-2-indan. The invention relates to a process for the preparation of alkyl-2-indane.
Das erfindungsgemäße Verfahren ist insbesondere im industriellen Maßstab wegen seiner Einfachheit, der geringen Zahl durch-" zuführender Verfahrensstufen und der erhaltenen ausgezeichneten Ausbeuten wirtschaftlich.The method according to the invention is particularly industrial Scale because of its simplicity, the small number by- " feeding process steps and the excellent yields obtained economically.
Die erfindungsgemäß erhaltenen Alkyl-2-indane sind insbesondere als wertvolle Zwischenprodukte für die Synthese bestimmter Heilmittel verwendbar.The alkyl-2-indanes obtained according to the invention are in particular useful as valuable intermediates for the synthesis of certain medicinal products.
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Alkyl-2-indan der Formel (IV):The invention relates to a process for the preparation of alkyl-2-indane of the formula (IV):
(IV)(IV)
in der R eine niedrige, kettenförmige oder verzweigte C.-C,--Alkylgruppe oder eine C^-C^-Cycloalky!gruppe darstellt, dasin which R is a lower, chain-like or branched C.-C, - alkyl group or a C 1 -C 4 cycloalkyl group, the
709814/1057709814/1057
dadurch gekennzeichnet ist, daß manis characterized in that one
a) ein aromatisches Keton der Formel (I):a) an aromatic ketone of formula (I):
(D(D
in der R die oben gegebene Bedeutung besitzt, mit Formaldehyd oder einer formaldehydbildenden Vorstufe in basischem Milieu und in einem organischen polaren Lösungsmittel zu einem Ketol der Formel (II):in which R has the meaning given above, with formaldehyde or a formaldehyde-forming precursor in a basic medium and in an organic polar solvent to a ketol of the formula (II):
IlIl
C - CH - RC - CH - R
CH2OH (II)CH 2 OH (II)
umsetzt, in der R die oben gegebene Bedeutung besitzt,converts, in which R has the meaning given above,
b) das Ketol der Formel (I) in stark saurem Milieu zu demb) the ketol of the formula (I) in a strongly acidic medium to the
Indanon der Formel (III)Indanone of formula (III)
(III)(III)
cyclisiert, in der R die oben gegebene Bedeutung besitzt, und c) das Indanon zu dem gewünschten Alkyl-2-indan reduziert.cyclized, in which R has the meaning given above, and c) reduces the indanone to the desired alkyl-2-indane.
Der Einsatz eines organischen polaren Lösungsmittels, wie z.B. Tetrahydrofuran, Dimethylformamid, Hexamethylphosphortriamid oder Dimethylsulfoxid in der Kondensationsstufe a) des erfindungsgemäßen Verfahrens ermöglicht eine beträchtliche Verbesserung der Ausbeute und eine Verminderung der Menge an eingesetztem Ausgangsketon unter im übrigen völlig gleichen Bedingungen. The use of an organic polar solvent such as tetrahydrofuran, dimethylformamide, hexamethylphosphoric triamide or dimethyl sulfoxide in the condensation stage a) of the invention Process enables a considerable improvement in the yield and a reduction in the amount used Starting ketone under otherwise completely identical conditions.
709814/1057709814/1057
Eins der bevorzugten polaren organischen Lösungsmittel ist Dimethylsulfoxid.One of the preferred polar organic solvents is dimethyl sulfoxide.
In die Verfahrensstufe'a) kann man ohne Unterschied das Formaldehyd oder das "Trioxymethylen", das eine cyclische trimerisierte Form des Formaldehyds darstellt, einsetzen.The formaldehyde can be used in process stage a) without a difference or the "trioxymethylene" which trimerized a cyclic one Form of formaldehyde is used.
Das erfindungsgemäße Verfahren ist besonders nützlich zur Herstellung von Alkyl-2-indanen, bei denen der Alkylrest ein Äthyl- oder Isopropylrest ist.The method of the invention is particularly useful for manufacture of alkyl-2-indanes, in which the alkyl radical is a Is ethyl or isopropyl radical.
Die in Stufe b) verwendete starke Säure kann insbesondere Schwefelsäure oder Phosphorsäure sein.The strong acid used in step b) can in particular be sulfuric acid or phosphoric acid.
Die Reduktion in Stufe c) kann durch klassische Clemmensen- oder Wolf-Kishner-Reduktion oder durch katalytische Hydrierung des Indanons der Formel III erfolgen.The reduction in stage c) can be carried out by classical Clemmensen or Wolf-Kishner reduction or by catalytic hydrogenation of the indanone of the formula III.
Um das basische Milieu der Stufe a) zu erzeugen, kann man beispielsweise Natriumhydroxid, Kaliumhydroxid, ein Alkoholat, ein quartäres Ammoniumhydroxid, ein Carbonat usw. verwenden.In order to generate the basic medium of stage a), one can, for example Use sodium hydroxide, potassium hydroxide, an alcoholate, a quaternary ammonium hydroxide, a carbonate, etc.
Unter einer formaldehydbildenden Vorstufe versteht man eine polykondensierte Form des Formaldehyds, die unter den Bedingungen der Stufe a) Formaldehyd freisetzt. Hier kann man z.B. das Trioxymethylen nennen.A formaldehyde-forming precursor is understood to be a polycondensed form of formaldehyde under the conditions the stage a) releases formaldehyde. Trioxymethylene can be mentioned here, for example.
Die Erfindung wird durch die folgenden Beispiele verdeutlicht, die erläuternd, aber nicht einschränkend gegeben werden.The invention is illustrated by the following examples, which are given by way of illustration but not of limitation.
Isopropyl-2-phenyl-1-propanol-3-on — 1 Formel (II) R= IsopropylIsopropyl-2-phenyl-1-propanol-3-one - 1 Formula (II) R = isopropyl
7098U/10577098U / 1057
Zu einer Lösung von 18oo g Isovalerophenon und 333 g Trioxymethylen in 55o ml Dimethylsulfoxid gibt man portionsweise 184 ml normaler äthanolischer Kalilauge bei 2o C zu. Die Reaktionstemperatur steigt fortschreitend von 2o bis 45°C und die Lösung wird klar. Nach beendeter Zugabe rührt man 3 h lang, wobei man die Reaktion auf Raumtemperatur abkühlen läßt; man läßt eine Nacht stehen und gibt dann Wasser und Eis zu und extrahiert mit Äther. Die Ätherphase wird dreimal mit Wasser gewaschen, dann über Natriumsulfat getrocknet. Der Äther wird über Vakuum abgezogen und man erhält 2o66 g Isopropyl-2-phenyl-1-propanol-3-on—1 in Form von weißen Kristallen, F = 46-48 C. Dieses Ketol wird als solches ohne jede weitere Reinigung für folgende Verfahrensschritte eingesetzt; man kann es jedoch, falls gewünscht, destillieren. Kp9 =145-15o°C (Ausbeute 97 %)184 ml of normal ethanolic potassium hydroxide solution are added in portions to a solution of 18oo g of isovalerophenone and 333 g of trioxymethylene in 55o ml of dimethyl sulfoxide. The reaction temperature increases progressively from 20 to 45 ° C and the solution becomes clear. When the addition is complete, the mixture is stirred for 3 hours, the reaction being allowed to cool to room temperature; it is left to stand for one night and then water and ice are added and the mixture is extracted with ether. The ether phase is washed three times with water, then dried over sodium sulfate. The ether is stripped off in vacuo and 2o66 g of isopropyl-2-phenyl-1-propanol-3-one-1 are obtained in the form of white crystals, F = 46-48 C. This ketol is used as such without any further purification for the following Process steps used; however, it can be distilled if desired. Bp 9 = 145-15o ° C (yield 97%)
Äthyl-2-phenyl-1-propanol-3-on — 1 Formel (II) R= ÄthylEthyl-2-phenyl-1-propanol-3-one - 1 Formula (II) R = ethyl
Gemäß dem Verfahren nach Beispiel 1, jedoch unter Verwendung von 2oo g Butyrophenon, erhält man 232 g Äthyl-2-phenyl-1-propanol-3-on—1. Kp: 135-14o°C unter 2 Torr (Ausbeute 96°C).Following the procedure of Example 1, but using from 200 g of butyrophenone, 232 g of ethyl-2-phenyl-1-propanol-3-one-1 are obtained. Bp: 135-14 ° C under 2 torr (yield 96 ° C).
loo g Isopropyl-2-pheny1-1-propanol-3-on—1 werden während 15 min unter starkem Rühren, wobei man die Temperatur unter 6o°C hält, in 22o ml konzentrierte Schwefelsäure der Dichte ca. 1,84 g/cm eingetropft. Nach beendeter Zugabe kühlt man bis auf unter 5o°C ab und rührt 1 h lang, wobei man das Reaktionsgemisch langsam auf Raumtemperatur abkühlen läßt. Man stürzt auf Eis und extrahiert mit Äther. Es bildet sich ein Rückstand, der im Äther suspendiert bleibt. Man entfernt diesen Rückstand durch Dekantation und wäscht die Ätherphase mit:100 g of isopropyl-2-pheny1-1-propanol-3-one-1 are used during 15 min with vigorous stirring, keeping the temperature below 60 ° C, in 220 ml of concentrated sulfuric acid of density approx. 1.84 g / cm dripped in. When the addition is complete, the mixture is cooled to below 50 ° C. and stirred for 1 hour, the reaction mixture being stirred let cool slowly to room temperature. It is thrown onto ice and extracted with ether. It imagines Residue that remains suspended in the ether. This residue is removed by decantation and the ether phase is washed with:
7098U/10577098U / 1057
- r- - r-
a) einer gesättigten wässrigen Natriumchloridlösunga) a saturated aqueous sodium chloride solution
b) einer 5 %igen Natriumhydroxidlösungb) a 5% sodium hydroxide solution
c) einer gesättigten wässrigen Natriumchloridlösung.c) a saturated aqueous sodium chloride solution.
Man trocknet mit Äther und konzentriert unter Vakuum ein. Man erhält so einen Rückstand von 83,8 g ( Ausbeute 92 % ), der unter Vakuum destilliert wird und 79 g reines Isopropyl-2-indanon-1 ergibt (Ausbeute 87 %) , Kp12T ·= 135°C.Dry with ether and concentrate under vacuum. This gives a residue of 83.8 g (yield 92%), which is distilled under vacuum and gives 79 g of pure isopropyl-2-indanone-1 (yield 87%), boiling point 12T = 135.degree.
Beispiel 4 Äthyl-2-indanon-1 Formel (III) R = ÄthylExample 4 Ethyl-2-indanone-1 Formula (III) R = ethyl
Nach dem Verfahren des Beispiels 3, jedoch aus 1oo g Äthyl-2-phenyl-i-propanol-3-on—1 erhält man 84,5 g Äthyl-2-indanon-1. Kp18Torr = 144°C (Ausbeute 94 %).Following the procedure of Example 3, but from 100 g of ethyl-2-phenyl-i-propanol-3-one-1, 84.5 g of ethyl-2-indanone-1 are obtained. Kp 18Torr = 144 ° C (yield 94%).
Man rührt 5 min lang ein Gemisch von 52o g Zn, 52 g HgCl«* 52o ml destillierten Wassers und 26 ml konzentrierter Salzsäure. Man beendet das Rühren und dekantiert. Anschließend gibt man zum Gemisch unter gutem Rühren 33o ml destilliertes Wasser und 52o ml konzentrierte Salzsäure, dann erwärmt man am Rückfluss.A mixture of 52o g of Zn and 52 g of HgCl is stirred for 5 minutes. 520 ml of distilled water and 26 ml of concentrated hydrochloric acid. Stop stirring and decant. Afterward 33o ml of distilled water and 52o ml of concentrated hydrochloric acid are added to the mixture, with thorough stirring, and the mixture is then heated at the reflux.
Man setzt anschließend unter gutem Rühren eine Lösung von 468 g Isopropyl-2-indanon-1 in 52o ml Äthanol tropfenweise dem Reaktionsgemisch zu. Das Gemisch wird 3 h lang am Rückfluss gehalten. Man gibt anschließend in kleinen Anteilen 52o ml konzentrierte Salzsäure zu und hält erneut 3 h lang am Rückfluss.A solution of is then set with thorough stirring 468 g of isopropyl-2-indanon-1 in 52o ml of ethanol drop by drop Reaction mixture too. The mixture is refluxed for 3 hours. Then add 52o ml concentrated in small portions Hydrochloric acid is added and refluxed again for 3 h.
Nach Ablauf dieser 3 h gibt man noch einmal 5oo ml konzentrierte Salzsäure in kleinen Anteilen zu und hält erneut 3 h amAt the end of these 3 hours, another 500 ml of concentrated product are added Hydrochloric acid is added in small proportions and lasts again for 3 h
7 098 H/10577 098 H / 1057
Rückfluss. Das Reaktionsgemisch wird dann abgekühlt, mit einem Gemisch aus Wasser und Eis verdünnt und das Produkt mit Äther extrahiert, den man mit Wasser, mit einer 5 %igen Natriumlaugelösung und erneut mit Wasser wäscht. Nach dem Trocknen über Natriumsulfat und Abdampfen des Äthers erhält man 463 g Rückstand, der unter Vakuum fraktioniert wird. Man erhält soReflux. The reaction mixture is then cooled with a Mixture of water and ice is diluted and the product is extracted with ether, which is washed with water with a 5% sodium hydroxide solution and washes again with water. After drying over sodium sulfate and evaporation of the ether, 463 g are obtained Residue which is fractionated under vacuum. You get so
381.1 g Isopropyl-2-indan, das in Form von weißen Nadeln kristallisiert (E = 42°C). Kp1 = 118-12o°C.381.1 g of isopropyl-2-indane, which crystallizes in the form of white needles (E = 42 ° C). Bp 1 = 118-12o ° C.
Äthyl-2-indanEthyl 2- indan
Formel (IV) R= Äthyl Formula (IV) R = ethyl
Nach dem Verfahren wie in Beispiel 5, jedoch ausgehend vonFollowing the procedure as in Example 5, but starting from
119.2 g Äthyl-2-indanon-1, erhält man nach dem Destillieren unter Vakuum 98,5 g Äthyl-2-indan. KP13Torr = 97-1 oo°C.119.2 g of ethyl-2-indanone-1 are obtained after distilling under vacuum 98.5 g of ethyl-2-indane. K P 13 Torr = 97-100 ° C.
7098U/10577098U / 1057
Claims (5)
a) ein aromatisches Keton der Formel (I):in which R is a chain-like or branched lower C 1 -C 5 -alkyl group or a C ^ -Cy -cycloalkyl group, characterized in that one
a) an aromatic ketone of formula (I):
C-CH-RO
C-CH-R
c) das Indanon zu dem gewünschten Alkyl-2-indan reduziert.cyclized, in which R has the meaning given above, and
c) reducing the indanone to the desired alkyl-2-indane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7529658A FR2325625A1 (en) | 1975-09-26 | 1975-09-26 | PROCESS FOR PREPARING 2-ALKYL INDANE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2643074A1 true DE2643074A1 (en) | 1977-04-07 |
Family
ID=9160530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762643074 Withdrawn DE2643074A1 (en) | 1975-09-26 | 1976-09-24 | METHOD FOR PRODUCING ALKYL-2-INDAN |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5257157A (en) |
| AR (1) | AR210162A1 (en) |
| AT (1) | AT346322B (en) |
| AU (1) | AU497933B2 (en) |
| BE (1) | BE846528A (en) |
| CA (1) | CA1062286A (en) |
| CH (1) | CH595302A5 (en) |
| CS (1) | CS204996B2 (en) |
| DD (1) | DD126332A5 (en) |
| DE (1) | DE2643074A1 (en) |
| DK (1) | DK424676A (en) |
| ES (1) | ES451697A1 (en) |
| FR (1) | FR2325625A1 (en) |
| GB (1) | GB1500229A (en) |
| GR (1) | GR58459B (en) |
| HU (1) | HU172481B (en) |
| NL (1) | NL7610336A (en) |
| NO (1) | NO143703C (en) |
| PT (1) | PT65587B (en) |
| SE (1) | SE417086B (en) |
| SU (1) | SU615847A3 (en) |
| ZA (1) | ZA765536B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5975133U (en) * | 1982-11-12 | 1984-05-22 | 金鹿「こて」工業株式会社 | power wire brush |
| FR2784986A1 (en) * | 1998-10-26 | 2000-04-28 | Rhodia Chimie Sa | Preparation of indanone and thioindanone phytosanitary agents by cyclizing substituted aromatic compound in fluorinated organic sulfonic acid |
| FR2788764B1 (en) * | 1999-01-25 | 2001-03-02 | Rhodia Chimie Sa | PROCESS FOR THE PREPARATION OF AN INDANONE OR THIOINDANONE COMPOUND |
| RU2768714C2 (en) * | 2020-05-22 | 2022-03-24 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный лесотехнический университет имени С.М. Кирова" | Method for synthesis of 3-arylindan-1-ones by reaction of super-electrophilic aromatic substitution of cinnamic nitriles |
-
1975
- 1975-09-26 FR FR7529658A patent/FR2325625A1/en active Granted
-
1976
- 1976-08-23 GR GR51532A patent/GR58459B/en unknown
- 1976-08-26 GB GB35449/76A patent/GB1500229A/en not_active Expired
- 1976-09-09 HU HU76HE00000720A patent/HU172481B/en unknown
- 1976-09-13 PT PT65587A patent/PT65587B/en unknown
- 1976-09-13 CH CH1161876A patent/CH595302A5/xx not_active IP Right Cessation
- 1976-09-14 JP JP51110660A patent/JPS5257157A/en active Granted
- 1976-09-15 CA CA261,303A patent/CA1062286A/en not_active Expired
- 1976-09-15 ZA ZA765536A patent/ZA765536B/en unknown
- 1976-09-16 NL NL7610336A patent/NL7610336A/en not_active Application Discontinuation
- 1976-09-17 AR AR264748A patent/AR210162A1/en active
- 1976-09-17 AU AU17879/76A patent/AU497933B2/en not_active Expired
- 1976-09-20 ES ES451697A patent/ES451697A1/en not_active Expired
- 1976-09-21 DK DK424676A patent/DK424676A/en not_active Application Discontinuation
- 1976-09-23 AT AT707376A patent/AT346322B/en not_active IP Right Cessation
- 1976-09-23 SU SU762403409A patent/SU615847A3/en active
- 1976-09-24 CS CS766203A patent/CS204996B2/en unknown
- 1976-09-24 DE DE19762643074 patent/DE2643074A1/en not_active Withdrawn
- 1976-09-24 DD DD194981A patent/DD126332A5/xx unknown
- 1976-09-24 NO NO763272A patent/NO143703C/en unknown
- 1976-09-24 BE BE2055330A patent/BE846528A/en unknown
- 1976-09-24 SE SE7610637A patent/SE417086B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU172481B (en) | 1978-09-28 |
| NO143703C (en) | 1981-04-08 |
| SE7610637L (en) | 1977-03-27 |
| ATA707376A (en) | 1978-03-15 |
| CA1062286A (en) | 1979-09-11 |
| BE846528A (en) | 1977-01-17 |
| CS204996B2 (en) | 1981-04-30 |
| CH595302A5 (en) | 1978-02-15 |
| GB1500229A (en) | 1978-02-08 |
| JPS5257157A (en) | 1977-05-11 |
| SE417086B (en) | 1981-02-23 |
| FR2325625B1 (en) | 1980-08-01 |
| NO143703B (en) | 1980-12-22 |
| ES451697A1 (en) | 1977-08-16 |
| ZA765536B (en) | 1977-08-31 |
| AU497933B2 (en) | 1979-01-25 |
| AU1787976A (en) | 1978-03-23 |
| PT65587B (en) | 1978-03-28 |
| GR58459B (en) | 1977-10-12 |
| NL7610336A (en) | 1977-03-29 |
| SU615847A3 (en) | 1978-07-15 |
| NO763272L (en) | 1977-03-29 |
| PT65587A (en) | 1976-10-01 |
| FR2325625A1 (en) | 1977-04-22 |
| JPS543870B2 (en) | 1979-02-27 |
| DD126332A5 (en) | 1977-07-13 |
| DK424676A (en) | 1977-03-27 |
| AR210162A1 (en) | 1977-06-30 |
| AT346322B (en) | 1978-11-10 |
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