NO125629B - - Google Patents
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- Publication number
- NO125629B NO125629B NO165161A NO16516166A NO125629B NO 125629 B NO125629 B NO 125629B NO 165161 A NO165161 A NO 165161A NO 16516166 A NO16516166 A NO 16516166A NO 125629 B NO125629 B NO 125629B
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- aluminum
- alcohol
- aluminum chloride
- minutes
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 20
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 18
- 229910052782 aluminium Inorganic materials 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 5
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960002523 mercuric chloride Drugs 0.000 description 1
- 229960003671 mercuric iodide Drugs 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
Description
Fremgangsmåte til fremstilling av aluminium-alkoholater. Process for the production of aluminum alcoholates.
Den foreliggende oppfinnelse angår en The present invention relates to a
fremgangsmåte til fremstilling av aluminiumalkoholater. Mer spesielt går oppfinnelsen ut på en forbedret fremgangsmåte til omsetning av aluminium og en alkohol som har fra 1—4 carbonatomer, for fremstilling av alkoholater eller alkoksyder. method for the production of aluminum alcoholates. More particularly, the invention concerns an improved process for reacting aluminum and an alcohol having from 1 to 4 carbon atoms, for the production of alcoholates or alkoxides.
Forbindelser med formelen Al(OR)3, Compounds with the formula Al(OR)3,
hvor R betyr en lavere uforgrenet eller forgrenet alifatisk carbonkjede, er hvite faste stoffer som er nyttige reagenser ved selek-tiv reduksjon av aldehyders og ketoners carbonylgrupper ifølge Meerwein-Poon-dorf-Verley-metoden. Disse forbindelser fremstilles vanligvis ved at aluminiumpulver bringes til å reagere med en absolutt alkohol under samtidig anvendelse av små mengder mercuriklorid eller -jodid som katalysator. where R means a lower unbranched or branched aliphatic carbon chain, are white solids which are useful reagents in the selective reduction of the carbonyl groups of aldehydes and ketones according to the Meerwein-Poondorf-Verley method. These compounds are usually prepared by reacting aluminum powder with an absolute alcohol while simultaneously using small amounts of mercuric chloride or iodide as a catalyst.
En vesentlig ulempe ved utførelsen av A significant disadvantage in the execution of
den ovennevnte reaksjon har vært nødven-digheten av å anvende vannfri eller absolutt alkohol, og ennvidere at det har vært nødvendig å treffe særlige sikkerhetsforholdsregler for å unngå fuktighetsdannelse the above-mentioned reaction has been the necessity of using anhydrous or absolute alcohol, and further that it has been necessary to take special safety precautions to avoid moisture formation
i reaksjonsbeholderen. Selv om omkost-ningene ved fremstilling av aluminiumal-koholet har vært ganske betydelige fordi, prosessen skulle utføres under vannfri be-tingelser, har det hittil vært den alminne-lige oppfatning at slike fremgangsmåter var nødvendige for å unngå dekompone-ring av sluttproduktet ved eventuell kon-takt med vann eller vanndamp som måtte befinne seg i systemet. in the reaction vessel. Although the costs of producing the aluminum alcohol have been quite significant because the process had to be carried out under anhydrous conditions, it has been the general opinion until now that such methods were necessary to avoid decomposition of the end product in the event of contact with water or water vapor that may be in the system.
En hensikt med den foreliggende oppfinnelse er å skaffe en fremgangsmåte hvor man unngår nødvendigheten av å anvende vannfrie utgangsmaterialer. Videre er det en hensikt med oppfinnelsen å skaffe en fremgangsmåte som gjør det unødvendig å treffe særlige sikkerhetsforholdsregler for å unngå dannelse av fuktighet i reaksjonsbeholderen. Ytterligere hensikter med og fordeler ved oppfinnelsen vil fremgå av den følgende beskrivelse. One purpose of the present invention is to provide a method in which the necessity of using anhydrous starting materials is avoided. Furthermore, it is an aim of the invention to provide a method which makes it unnecessary to take special safety precautions to avoid the formation of moisture in the reaction container. Further purposes and advantages of the invention will be apparent from the following description.
Ifølge oppfinnelsen er alkoholen ikke gjort vannfri ved forutgående behandling, og reaksjonen utføres i nærvær av aluminiumklorid og eventuelt en ytterligere katalysator. According to the invention, the alcohol is not made anhydrous by prior treatment, and the reaction is carried out in the presence of aluminum chloride and possibly an additional catalyst.
Det har vist seg at reaksjonen mellom aluminium og alkohol ved tilstedeværelse av aluminiumklorid foregår glatt og full-føres i løpet av relativt kort tid uten at det har vist seg nødvendig å forbehandle alkoholen for å gjøre den vannfri, og uten at det har vært nødvendig å treffe særlige sikkerhetsforholdsregler mot dannelse av fuktighet under reaksjonen. It has been shown that the reaction between aluminum and alcohol in the presence of aluminum chloride takes place smoothly and is completed within a relatively short time without it having been found necessary to pre-treat the alcohol to make it anhydrous, and without it having been necessary to take special safety measures against the formation of moisture during the reaction.
Den alkohol som ved fremgangsmåten ifølge oppfinnelsen anvendes som utgangs-materiale, kan være en hvilken som helst alkohol som inneholder en lavere uforgrenet eller forgrenet alifatisk kullvannstoff-kjede. Særlig egnet for reaksjonen er isopropylalkohol, men andre alkoholer som propylalkohol, butylalkohol osv. kan også anvendes. De alkoholer som kommer i be-traktning ved den foreliggende oppfinnelse, er slike som ikke har vært forbehandlet for fjernelse av vanninnhold. The alcohol used in the process according to the invention as starting material can be any alcohol containing a lower unbranched or branched aliphatic hydrocarbon chain. Particularly suitable for the reaction is isopropyl alcohol, but other alcohols such as propyl alcohol, butyl alcohol etc. can also be used. The alcohols that come into consideration in the present invention are those that have not been pre-treated to remove water content.
De øvrige reagenser av grunnstoffet aluminium i en hvilken som helst av dets vanligvis forekommende fysiske former, som aluminiumpulver, aluminiumstrimler, aluminiumfolie, aluminiumspon eller alu-miniumkuler. The other reagents of the element aluminum in any of its commonly occurring physical forms, such as aluminum powder, aluminum strips, aluminum foil, aluminum shavings or aluminum balls.
Reaksjonen mellom aluminium og alkohol foregår etter følgende ligning: 2 Al + 6ROH ^2Al(OR)3 + 3H2The reaction between aluminum and alcohol takes place according to the following equation: 2 Al + 6ROH ^2Al(OR)3 + 3H2
hvor R har den ovenfor angitte betydning. where R has the above meaning.
Ved utførelsen av reaksjonen anbrin-ges alkoholen, aluminiumkloridet og alu-miniumet i en reaksjonssone sammen med en liten mengde katalysator, som mercuriacetat. Tilsetningsrekkefølgen er av liten betydning, idet reaksjonen først begynner når reaksjonsblandingen opp-varmes til tilbakeløps-temperatur. Etterat denne temperatur er nådd, fjernes varmekilden, og reaksjonen fortsetter inntil den er fullført. Hvis reaksjonen er for voldsom, stanses den imidlertid ved av-kjøling av reaksjonsbeholderen. Reaksjonen tar mellom en halv time og én time, og den er fullført når der ikke frigjøres mer hydrogen. When carrying out the reaction, the alcohol, aluminum chloride and aluminum are placed in a reaction zone together with a small amount of catalyst, such as mercuric acetate. The order of addition is of little importance, as the reaction only begins when the reaction mixture is heated to reflux temperature. After this temperature is reached, the heat source is removed and the reaction continues until it is complete. If the reaction is too violent, however, it is stopped by cooling the reaction vessel. The reaction takes between half an hour and one hour, and it is complete when no more hydrogen is released.
Forholdet mellom reaksjonskomponen-tene er som følger: Der tilsettes minst tre mol alkohol for hvert mol aluminium og fortrinnsvis overskudd av alkohol, som lett kan fjernes ved destillasjon etterat reaksjonen er tilendebragt. Det har vist seg at en særlig fordelaktig sammensetning er en tilsetning av aluminiumklorid i konsen-trasjoner på omkring 0,2 til 2,0 vektpro-sent av den anvendte vektmengde alkohol. En konsentrasjon på 1 pst. aluminiumklorid har vist seg å være særlig anvende-lig i denne sammensetning. The ratio between the reaction components is as follows: At least three moles of alcohol are added for each mole of aluminum and preferably excess alcohol, which can be easily removed by distillation after the reaction has been completed. It has been found that a particularly advantageous composition is an addition of aluminum chloride in concentrations of about 0.2 to 2.0 percent by weight of the amount of alcohol used. A concentration of 1% aluminum chloride has proven to be particularly useful in this composition.
Oppfinnelsen skal illustreres ved ek-sempler: Eksempel 1: 27 g aluminiumpulver ble anbragt i en reaksjonsbeholder, og 0,5 g mercuriacetat ble tilsatt. Hertil ble ytterligere tilsatt 300 g 99 pst.'s isopropylalkohol og 4 g vannfri aluminiumklorid. Blandingen ble oppvarmet til tilbakeløpstemperaturen (82° C). oppvarmningen ble deretter avbrudt, og reaksjonen fortsatte, idet den ble avbrudt ved avkjøling når den ble for voldsom. Etter 35 minutters forløp ble der ikke av-gitt ytterligere hydrogen, og reaksjonsblandingen ble destillert i vakuum. Den resul-terende forbindelse med formelen Al-(OCH(CH3)2)3 var et hvitt, fast stoff med smeltepunkt på 118° C. The invention shall be illustrated by examples: Example 1: 27 g of aluminum powder was placed in a reaction container, and 0.5 g of mercuric acetate was added. 300 g of 99% isopropyl alcohol and 4 g of anhydrous aluminum chloride were further added to this. The mixture was heated to the reflux temperature (82°C). heating was then discontinued and the reaction continued, being terminated by cooling when it became too vigorous. After 35 minutes, no further hydrogen was released, and the reaction mixture was distilled in vacuo. The resulting compound with the formula Al-(OCH(CH3)2)3 was a white solid with a melting point of 118°C.
Eksempel 2: Følgende stoffer ble anbragt i en kolbe med påmontert tilbakeløpskondensator og varmekappe : 0,5 g mercuriacetat, 1,0 g aluminiumklorid, 300,0 g n-propylalkohol, Example 2: The following substances were placed in a flask with an attached reflux condenser and heating jacket: 0.5 g mercuric acetate, 1.0 g aluminum chloride, 300.0 g n-propyl alcohol,
27,0 g aluminiumpulver. 27.0 g aluminum powder.
Varmekappen ble oppvarmet og reak-sjonsblandingens temperatur steg til 45° C. På dette tidspunkt viste der seg en meget voldsom hydrogen-utvikling, og varmekappen ble fjernet og kolben avkjølet i vann-bad. Hydrogen-utviklingen fortsatte vold-somt, og reaksjonen ble regulert ved fort-satt avkjøling. 95 minutter senere var temperaturen 56° C, og hydrogen-utviklingen var meget langsom. På dette tidspunkt ble varmekappen igjen anbragt omkring kolben, og denne ble oppvarmet inntil alkoholen kokte under tilbakeløp. 15 minutter senere var reaksjonen tilendebragt, og reaksjonsblandingen ble avkjølet. Det fremkomne produkt var et hvitt, fast stoff med formelen Al-(0-CH2-CH2-CH3)3. The heating mantle was heated and the temperature of the reaction mixture rose to 45° C. At this point a very violent evolution of hydrogen appeared, and the heating mantle was removed and the flask cooled in a water bath. Hydrogen evolution continued violently, and the reaction was regulated by continued cooling. 95 minutes later the temperature was 56° C, and hydrogen evolution was very slow. At this point, the heating mantle was again placed around the flask, and this was heated until the alcohol boiled under reflux. 15 minutes later the reaction was complete and the reaction mixture was cooled. The resulting product was a white solid with the formula Al-(0-CH2-CH2-CH3)3.
Eksempel 3. Example 3.
Følgende stoffer ble anbragt i en 1-liters kolbe med påmontert tilbakeløps-kondensator og varmekappe: 0,5 g mercuriacetat, 1,0 g aluminiumklorid, 300,0 g n-butylalkohol, The following substances were placed in a 1-liter flask with an attached reflux condenser and heating jacket: 0.5 g mercuric acetate, 1.0 g aluminum chloride, 300.0 g n-butyl alcohol,
27,0 g aluminiumpulver. 27.0 g aluminum powder.
Varmekappen ble oppvarmet, og temperaturen steg til 50° C; på dette tidspunkt var hydrogen-utviklingen voldsom. Varmekappen ble fjernet og kolben avkjølet i 20 minutter. Hydrogenutviklingen under av-kjølingen var voldsom. Etter utløpet av de 20 minutter var temperaturen 70°C, og hydrogen-utviklingen langsom. Etter ytterligere 20 minutters forløp ble varmekappen oppvarmet påny og reaksjonsblandingen kokt under tilbakeløp. Ved utløpet av en tredje periode på 20 minutter ble varmekappen fjernet og reaksjonsblandingen av-kjølet. Det fremkomne produkt var et hvitt, fast stoff med formelen Al-(OCH-CH2-CH2-CH3)3. The heating mantle was heated, and the temperature rose to 50° C; at this point, hydrogen evolution was rampant. The heating mantle was removed and the flask cooled for 20 minutes. The evolution of hydrogen during cooling was violent. After the expiration of the 20 minutes, the temperature was 70°C, and the hydrogen evolution was slow. After a further 20 minutes, the heating mantle was heated again and the reaction mixture boiled under reflux. At the end of a third period of 20 minutes, the heating jacket was removed and the reaction mixture was cooled. The resulting product was a white solid with the formula Al-(OCH-CH2-CH2-CH3)3.
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL6513426A NL6513426A (en) | 1965-10-16 | 1965-10-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO125629B true NO125629B (en) | 1972-10-09 |
Family
ID=19794388
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO165161A NO125629B (en) | 1965-10-16 | 1966-10-14 |
Country Status (12)
Country | Link |
---|---|
AT (1) | AT265240B (en) |
BE (1) | BE688260A (en) |
CH (1) | CH481888A (en) |
DE (1) | DE1272288B (en) |
DK (1) | DK117701B (en) |
ES (1) | ES332252A1 (en) |
FR (1) | FR1496435A (en) |
GB (1) | GB1138750A (en) |
IL (1) | IL26663A (en) |
NL (1) | NL6513426A (en) |
NO (1) | NO125629B (en) |
SE (1) | SE338985B (en) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL135679C (en) * | 1968-11-12 | 1900-01-01 | ||
NL6914306A (en) * | 1969-09-20 | 1971-03-23 | ||
US3862230A (en) * | 1969-09-20 | 1975-01-21 | Stamicarbon | Continuous preparation of cyclohexanone oxime |
DE2029114C2 (en) * | 1970-06-12 | 1982-07-01 | Stamicarbon B.V., 6160 Geleen | Process for the preparation of cyclohexanone oxime |
US3625835A (en) * | 1970-06-15 | 1971-12-07 | Stamicarbon | Process for the recovery of cyclohexanone oxime by plural stage, vacuum distillation per a |
NL7008838A (en) * | 1970-06-17 | 1971-12-21 | ||
DE2508247C3 (en) * | 1975-02-26 | 1981-03-12 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of cyclohexanone oxime |
US4104359A (en) * | 1977-02-28 | 1978-08-01 | Amax Inc. | Regeneration of organic extractants containing α-hydroxyoximes |
DE3942334A1 (en) * | 1989-12-21 | 1991-06-27 | Basf Ag | METHOD FOR PROCESSING HYDROXYLAMMONIUM AND AMMONIUM SALTS CONTAINING AQUEOUS NUTS |
US5254734A (en) * | 1991-02-13 | 1993-10-19 | Mitsubishi Kasei Corporation | Method for preparing an oxime |
JP2003535842A (en) | 2000-06-05 | 2003-12-02 | ディーエスエム エヌ.ブイ. | Method for producing cyclohexanone oxime |
JP2003535841A (en) | 2000-06-05 | 2003-12-02 | ディーエスエム エヌ.ブイ. | Method for producing cyclohexanone oxime |
EP1318141A1 (en) | 2001-12-04 | 2003-06-11 | Dsm Nv | Process for treating an aqueous medium containing phosphate, cyclohexanone and cyclohexanone oxime |
BR0117189B1 (en) | 2001-12-04 | 2011-08-09 | A process for treating an aqueous medium containing cyclohexanone oxime and cyclohexanone. | |
MXPA04005413A (en) * | 2001-12-04 | 2004-10-11 | Dsm Ip Assets Bv | Process for treating an aqueous medium containing phosphate salt and organic compounds. |
KR101078927B1 (en) * | 2003-01-30 | 2011-11-01 | 디에스엠 아이피 어셋츠 비.브이. | Process for treating an organic solution comprising cyclohexanone oxime cyclohexanone and an organic solvent |
TW200829544A (en) * | 2007-01-05 | 2008-07-16 | China Petrochemical Dev Corp | Method for preparing cyclohexanone oxime |
CN103193672B (en) * | 2013-03-11 | 2014-09-17 | 浙江圣安化工有限公司 | Distillation method of oxime |
CN105384656B (en) * | 2015-10-23 | 2017-08-25 | 中石化南京工程有限公司 | A kind of method of cyclohexanone oximate |
CN105348145B (en) * | 2015-10-23 | 2018-02-06 | 中石化南京工程有限公司 | The method of ammonia type flue gas desulfurizing by-product cyclohexanone oxime |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2270204A (en) * | 1938-11-28 | 1942-01-13 | Du Pont | Process of producing oximes |
DE1081884B (en) * | 1959-02-13 | 1960-05-19 | Basf Ag | Process for the preparation of cyclododecanone oxime |
GB972107A (en) * | 1962-09-01 | 1964-10-07 | Basf Ag | Production of oximes of cycloaliphatic ketones |
NL301053A (en) * | 1963-11-27 |
-
1965
- 1965-10-16 NL NL6513426A patent/NL6513426A/xx unknown
-
1966
- 1966-10-06 GB GB44743/66A patent/GB1138750A/en not_active Expired
- 1966-10-07 DE DEP1272A patent/DE1272288B/en active Pending
- 1966-10-07 AT AT942866A patent/AT265240B/en active
- 1966-10-10 IL IL26663A patent/IL26663A/en unknown
- 1966-10-10 CH CH1454566A patent/CH481888A/en not_active IP Right Cessation
- 1966-10-12 FR FR79609A patent/FR1496435A/en not_active Expired
- 1966-10-14 NO NO165161A patent/NO125629B/no unknown
- 1966-10-14 BE BE688260D patent/BE688260A/xx not_active IP Right Cessation
- 1966-10-14 ES ES0332252A patent/ES332252A1/en not_active Expired
- 1966-10-14 SE SE14007/66A patent/SE338985B/xx unknown
- 1966-10-17 DK DK535566AA patent/DK117701B/en unknown
Also Published As
Publication number | Publication date |
---|---|
DE1272288B (en) | 1968-07-11 |
AT265240B (en) | 1968-10-10 |
GB1138750A (en) | 1969-01-01 |
NL6513426A (en) | 1967-04-17 |
DK117701B (en) | 1970-05-25 |
CH481888A (en) | 1969-11-30 |
FR1496435A (en) | 1967-09-29 |
IL26663A (en) | 1970-09-17 |
ES332252A1 (en) | 1967-07-16 |
SE338985B (en) | 1971-09-27 |
BE688260A (en) | 1967-04-14 |
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