NO116162B - - Google Patents
Info
- Publication number
- NO116162B NO116162B NO153337A NO15333764A NO116162B NO 116162 B NO116162 B NO 116162B NO 153337 A NO153337 A NO 153337A NO 15333764 A NO15333764 A NO 15333764A NO 116162 B NO116162 B NO 116162B
- Authority
- NO
- Norway
- Prior art keywords
- aluminum
- stated
- olefins
- reaction
- hydrogen
- Prior art date
Links
- 229910052782 aluminium Inorganic materials 0.000 claims description 195
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 193
- 238000000034 method Methods 0.000 claims description 65
- 150000001336 alkenes Chemical class 0.000 claims description 63
- 239000003054 catalyst Substances 0.000 claims description 57
- 238000006243 chemical reaction Methods 0.000 claims description 55
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 20
- -1 alkyl aluminum halides Chemical class 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000004411 aluminium Substances 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 claims description 4
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical class I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 claims description 4
- 239000000428 dust Substances 0.000 claims description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 150000002896 organic halogen compounds Chemical class 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- FCMKFNXOHUYWRU-UHFFFAOYSA-N [Cl].[Cr] Chemical compound [Cl].[Cr] FCMKFNXOHUYWRU-UHFFFAOYSA-N 0.000 claims 1
- 238000005336 cracking Methods 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000003245 coal Substances 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 7
- 239000011630 iodine Substances 0.000 description 7
- 229910052740 iodine Inorganic materials 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 5
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical class CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- TUAINSCBEUWUOI-UHFFFAOYSA-M iodo(dipropyl)alumane Chemical compound [I-].CCC[Al+]CCC TUAINSCBEUWUOI-UHFFFAOYSA-M 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000007591 painting process Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000007306 turnover Effects 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WATVKUKXTKWHRP-UHFFFAOYSA-N [K].[Br] Chemical compound [K].[Br] WATVKUKXTKWHRP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 150000001398 aluminium Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- ICKSOVDWLBHVCG-UHFFFAOYSA-N bis(4-methylpentyl)alumane Chemical compound C(CCC(C)C)[AlH]CCCC(C)C ICKSOVDWLBHVCG-UHFFFAOYSA-N 0.000 description 1
- JKFJJYOIWGFQGI-UHFFFAOYSA-M bromo-bis(2-methylpropyl)alumane Chemical compound [Br-].CC(C)C[Al+]CC(C)C JKFJJYOIWGFQGI-UHFFFAOYSA-M 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical class CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000011143 downstream manufacturing Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002370 organoaluminium group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003886 thermite process Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/42—Nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR935564A FR1427622A (fr) | 1963-05-21 | 1963-05-21 | Nouveaux dérivés du nitro-5 pyrrole et leur préparation |
| FR945139A FR3093M (fr) | 1963-05-21 | 1963-08-20 | Nouveaux dérivés du nitro-5 pyrrole et médicaments les contenant. |
| CH1541563A CH438319A (de) | 1963-05-21 | 1963-12-16 | Verfahren zur Herstellung von neuen Azepinderivaten |
| FR965763A FR86515E (fr) | 1963-05-21 | 1964-03-02 | Nouveaux dérivés du nitro-5 pyrrole et leur préparation |
| FR972256A FR1443065A (fr) | 1963-05-21 | 1964-04-24 | Préparation du méthyl-1 carbamoyl-2 nitro-5 pyrrole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116162B true NO116162B (sv) | 1969-02-10 |
Family
ID=27509516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO153337A NO116162B (sv) | 1963-05-21 | 1964-05-21 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3393201A (sv) |
| BE (1) | BE648172A (sv) |
| BR (1) | BR6459328D0 (sv) |
| CH (4) | CH438319A (sv) |
| DE (1) | DE1470205B1 (sv) |
| FI (1) | FI45041C (sv) |
| FR (5) | FR90M (sv) |
| GB (2) | GB1019126A (sv) |
| LU (1) | LU46111A1 (sv) |
| NL (2) | NL6405668A (sv) |
| NO (1) | NO116162B (sv) |
| OA (1) | OA00275A (sv) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1291099A (en) * | 1968-12-29 | 1972-09-27 | Dainippon Pharmaceutical Co | 4-nitropyrrole-2-carboxylic acid amide derivatives |
| US4046775A (en) * | 1973-04-11 | 1977-09-06 | Sterling Drug Inc. | 4,5-Dihalopyrrole-2-carboxamides |
| US3963480A (en) * | 1973-04-11 | 1976-06-15 | Sterling Drug Inc. | Herbicidal pyrrole-2-carboxamides |
| US4207237A (en) * | 1977-04-20 | 1980-06-10 | Mcneilab, Inc. | Preparation of pyrrole-2-acetates |
| US4216150A (en) * | 1978-10-16 | 1980-08-05 | Mcneil Lab, Inc. | Preparation of pyrrole-2-acetates |
| DE3143726C2 (de) * | 1981-11-04 | 1987-02-05 | Degussa Ag, 6000 Frankfurt | Optisch aktive Prolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| BR8906202A (pt) * | 1988-12-05 | 1990-09-25 | American Cyanamid Co | Processo e composicao para o controle de pragas de insetos,acaros e moluscos,composto para tal controle e processo para sua preparacao |
| US5286742A (en) * | 1992-11-03 | 1994-02-15 | American Cyanamid Company | Pyrrole thiocarboxamide insecticidal and acaricidal agents |
| US7082203B1 (en) | 2001-01-05 | 2006-07-25 | Niko Drakoulis | Wireless audio transmission method and apparatus for coupling audio players to audio receivers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2962503A (en) * | 1956-11-21 | 1960-11-29 | American Cyanamid Co | Nitropyrroles |
-
1960
- 1960-07-29 FR FR834525A patent/FR90M/fr active Active
-
1963
- 1963-05-21 FR FR935564A patent/FR1427622A/fr not_active Expired
- 1963-08-20 FR FR945139A patent/FR3093M/fr active Active
- 1963-12-16 CH CH1541563A patent/CH438319A/de unknown
-
1964
- 1964-03-02 FR FR965763A patent/FR86515E/fr not_active Expired
- 1964-04-22 OA OA50082A patent/OA00275A/xx unknown
- 1964-04-24 FR FR972256A patent/FR1443065A/fr not_active Expired
- 1964-05-18 US US368381A patent/US3393201A/en not_active Expired - Lifetime
- 1964-05-20 BR BR159328/64A patent/BR6459328D0/pt unknown
- 1964-05-20 BE BE648172A patent/BE648172A/fr unknown
- 1964-05-20 LU LU46111D patent/LU46111A1/xx unknown
- 1964-05-20 GB GB20886/64A patent/GB1019126A/en not_active Expired
- 1964-05-21 CH CH1870766A patent/CH438314A/fr unknown
- 1964-05-21 FI FI641087A patent/FI45041C/sv not_active Application Discontinuation
- 1964-05-21 NL NL6405668A patent/NL6405668A/xx unknown
- 1964-05-21 DE DE19641470205 patent/DE1470205B1/de not_active Withdrawn
- 1964-05-21 CH CH1870866A patent/CH438315A/fr unknown
- 1964-05-21 CH CH659764A patent/CH438309A/fr unknown
- 1964-05-21 NL NL646405652A patent/NL144601B/xx unknown
- 1964-05-21 NO NO153337A patent/NO116162B/no unknown
- 1964-12-15 GB GB50937/64A patent/GB1040739A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH438309A (fr) | 1967-06-30 |
| FI45041B (sv) | 1971-11-30 |
| FR90M (sv) | 1961-01-09 |
| FR1427622A (fr) | 1966-02-11 |
| FR86515E (fr) | 1966-02-25 |
| US3393201A (en) | 1968-07-16 |
| CH438319A (de) | 1967-06-30 |
| NL144601B (nl) | 1975-01-15 |
| BE648172A (fr) | 1964-11-20 |
| DE1470205B1 (de) | 1971-11-04 |
| BR6459328D0 (pt) | 1973-08-02 |
| NL6405668A (sv) | 1965-10-25 |
| GB1019126A (en) | 1966-02-02 |
| GB1040739A (en) | 1966-09-01 |
| CH438315A (fr) | 1967-06-30 |
| NL6405652A (sv) | 1964-11-23 |
| LU46111A1 (sv) | 1972-01-01 |
| FR3093M (fr) | 1965-02-01 |
| CH438314A (fr) | 1967-06-30 |
| FI45041C (sv) | 1972-03-10 |
| OA00275A (fr) | 1966-05-15 |
| FR1443065A (fr) | 1966-06-24 |
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