CA1075267A - Process for the manufacture of difluoromethyl 1,2,2-trifluoromethyl ether - Google Patents
Process for the manufacture of difluoromethyl 1,2,2-trifluoromethyl etherInfo
- Publication number
- CA1075267A CA1075267A CA267,244A CA267244A CA1075267A CA 1075267 A CA1075267 A CA 1075267A CA 267244 A CA267244 A CA 267244A CA 1075267 A CA1075267 A CA 1075267A
- Authority
- CA
- Canada
- Prior art keywords
- ether
- difluoromethyl
- chlorine
- hydrogen
- chf2
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title description 13
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 title description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000000460 chlorine Substances 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
- 239000011737 fluorine Substances 0.000 claims abstract description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000003054 catalyst Substances 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 238000003682 fluorination reaction Methods 0.000 claims description 11
- KQUULKREOKHZAM-UHFFFAOYSA-N 1-(difluoromethoxy)-1,2,2-trifluoroethane Chemical compound FC(F)OC(F)C(F)F KQUULKREOKHZAM-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 claims description 4
- GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 claims description 4
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 3
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 3
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 3
- FMSYTQMJOCCCQS-UHFFFAOYSA-L difluoromercury Chemical compound F[Hg]F FMSYTQMJOCCCQS-UHFFFAOYSA-L 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 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 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 claims description 2
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 13
- 229910002092 carbon dioxide Inorganic materials 0.000 description 12
- 239000001569 carbon dioxide Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000008246 gaseous mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJAOEWRGFJXSNM-UHFFFAOYSA-N 1-(difluoromethoxy)-1,2,2-trifluoroethene Chemical compound FC(F)OC(F)=C(F)F IJAOEWRGFJXSNM-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- 239000005457 ice water Substances 0.000 description 5
- YHJXKSXVTNXUBK-UHFFFAOYSA-N 1,2-dichloro-1-(difluoromethoxy)-1,2,2-trifluoroethane Chemical compound FC(F)OC(F)(Cl)C(F)(F)Cl YHJXKSXVTNXUBK-UHFFFAOYSA-N 0.000 description 4
- SWVAQDCBPXOVFY-UHFFFAOYSA-N 1-chloro-2-(difluoromethoxy)-1,1,2-trifluoroethane Chemical compound FC(F)OC(F)C(F)(F)Cl SWVAQDCBPXOVFY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- -1 compound difluoromethyl 1,2,2-trifluoroethyl ether Chemical class 0.000 description 4
- 239000012025 fluorinating agent Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- YKICUSOQECKQRR-UHFFFAOYSA-N 1,1,2-trifluoro-2-methoxyethane Chemical compound COC(F)C(F)F YKICUSOQECKQRR-UHFFFAOYSA-N 0.000 description 3
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- WZJQNLGQTOCWDS-UHFFFAOYSA-K cobalt(iii) fluoride Chemical compound F[Co](F)F WZJQNLGQTOCWDS-UHFFFAOYSA-K 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000001030 gas--liquid chromatography Methods 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 235000005074 zinc chloride Nutrition 0.000 description 3
- 239000011592 zinc chloride Substances 0.000 description 3
- ZAYDSIAOSDNLKX-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethoxy)ethane Chemical compound FC(F)C(F)OC(F)C(F)F ZAYDSIAOSDNLKX-UHFFFAOYSA-N 0.000 description 2
- ZUNSDEVCBWMHMO-UHFFFAOYSA-N 1,1,2-trifluoro-2-methoxyethene Chemical compound COC(F)=C(F)F ZUNSDEVCBWMHMO-UHFFFAOYSA-N 0.000 description 2
- VJRCJEYDBCJRNW-UHFFFAOYSA-N 1-bromo-2-(difluoromethoxy)-1,1,2-trifluoroethane Chemical compound FC(F)OC(F)C(F)(F)Br VJRCJEYDBCJRNW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000011132 calcium sulphate Nutrition 0.000 description 2
- 239000001175 calcium sulphate Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- OHLVGBXMHDWRRX-UHFFFAOYSA-N 1,1,1-trifluoro-2-methoxyethane Chemical compound COCC(F)(F)F OHLVGBXMHDWRRX-UHFFFAOYSA-N 0.000 description 1
- MUYXIJXXXAXQGD-UHFFFAOYSA-N 1,1,2-trifluoro-2-(fluoromethoxy)ethane Chemical compound FCOC(F)C(F)F MUYXIJXXXAXQGD-UHFFFAOYSA-N 0.000 description 1
- YRZIDZCEIGAEKL-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trichloromethoxy)ethane Chemical compound FC(F)C(F)OC(Cl)(Cl)Cl YRZIDZCEIGAEKL-UHFFFAOYSA-N 0.000 description 1
- GWSDMVRYBFKVTB-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoro-2-methoxyethane Chemical compound COC(F)(Cl)C(F)(F)Cl GWSDMVRYBFKVTB-UHFFFAOYSA-N 0.000 description 1
- PWRDNDDKMQRAJF-UHFFFAOYSA-N 1,2-dichloro-1-(dichloromethoxy)-1,2,2-trifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)OC(Cl)Cl PWRDNDDKMQRAJF-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OMAVNUYELOCMQR-UHFFFAOYSA-N 1-[chloro(difluoro)methoxy]-1,2,2-trifluoroethane Chemical compound FC(F)C(F)OC(F)(F)Cl OMAVNUYELOCMQR-UHFFFAOYSA-N 0.000 description 1
- LIFQIKMWFLTTNM-UHFFFAOYSA-N 1-bromo-1-(difluoromethoxy)-1,2,2-trifluoroethane Chemical compound FC(F)OC(F)(Br)C(F)F LIFQIKMWFLTTNM-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- IOCGMLSHRBHNCM-UHFFFAOYSA-N difluoromethoxy(difluoro)methane Chemical compound FC(F)OC(F)F IOCGMLSHRBHNCM-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- KGPPDNUWZNWPSI-UHFFFAOYSA-N flurotyl Chemical compound FC(F)(F)COCC(F)(F)F KGPPDNUWZNWPSI-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB50040/75A GB1503999A (en) | 1975-12-05 | 1975-12-05 | Preparation of halogenated methyl ethyl ethers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1075267A true CA1075267A (en) | 1980-04-08 |
Family
ID=10454426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,244A Expired CA1075267A (en) | 1975-12-05 | 1976-12-06 | Process for the manufacture of difluoromethyl 1,2,2-trifluoromethyl ether |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1129892A (en) * | 1979-03-12 | 1982-08-17 | Ross C. Terrell | Process for adjusting the halogen content of halogenated aliphatic ethers |
| CA1130322A (en) * | 1979-04-25 | 1982-08-24 | Airco, Inc. | Method for the dehalogenation of ethers |
| JP7138116B2 (ja) * | 2017-11-09 | 2022-09-15 | 関東電化工業株式会社 | １，２－ジクロロ－１－（２，２，２－トリフルオロエトキシ）エチレン、その製造方法及びその用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3461213A (en) * | 1966-10-03 | 1969-08-12 | Air Reduction | 1,1 difluoro-2,2-dichloroethyl difluoromethyl ether or an anesthetic agent |
| GB1499818A (en) * | 1974-12-06 | 1978-02-01 | Ici Ltd | Anaesthetic composition |
-
1975
- 1975-12-05 GB GBGB50040/75A patent/GB1503999A/en not_active Expired
-
1976
- 1976-12-02 SE SE7613545A patent/SE7613545L/xx unknown
- 1976-12-03 NO NO764138A patent/NO764138L/no unknown
- 1976-12-03 FR FR7636614A patent/FR2357510A1/fr active Pending
- 1976-12-03 DK DK544476A patent/DK544476A/da not_active Application Discontinuation
- 1976-12-03 FI FI763497A patent/FI763497A7/fi not_active Application Discontinuation
- 1976-12-04 IN IN2158/CAL/76A patent/IN143299B/en unknown
- 1976-12-06 JP JP51146436A patent/JPS5271407A/ja active Pending
- 1976-12-06 DE DE2655196A patent/DE2655196A1/de not_active Withdrawn
- 1976-12-06 CA CA267,244A patent/CA1075267A/en not_active Expired
-
1977
- 1977-08-12 FR FR7724929A patent/FR2351933A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2351933B1 (enrdf_load_stackoverflow) | 1981-01-09 |
| FR2351933A1 (fr) | 1977-12-16 |
| GB1503999A (en) | 1978-03-15 |
| NO764138L (enrdf_load_stackoverflow) | 1977-06-07 |
| JPS5271407A (en) | 1977-06-14 |
| DE2655196A1 (de) | 1977-06-16 |
| FR2357510A1 (fr) | 1978-02-03 |
| FI763497A7 (enrdf_load_stackoverflow) | 1977-06-06 |
| DK544476A (da) | 1977-06-06 |
| SE7613545L (sv) | 1977-06-06 |
| IN143299B (enrdf_load_stackoverflow) | 1977-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |