NO781207L - Fremgangsmaate for fremstilling av oksalsyreestere - Google Patents
Fremgangsmaate for fremstilling av oksalsyreestereInfo
- Publication number
- NO781207L NO781207L NO781207A NO781207A NO781207L NO 781207 L NO781207 L NO 781207L NO 781207 A NO781207 A NO 781207A NO 781207 A NO781207 A NO 781207A NO 781207 L NO781207 L NO 781207L
- Authority
- NO
- Norway
- Prior art keywords
- palladium
- complexes
- stated
- grams
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title description 6
- 235000006408 oxalic acid Nutrition 0.000 title description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 32
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 13
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
- 229910052763 palladium Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 11
- -1 aromatic arsines Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 230000002378 acidificating effect Effects 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003426 co-catalyst Substances 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003901 oxalic acid esters Chemical class 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical class [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 150000002527 isonitriles Chemical class 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- QKJAZPHKNWSXDF-UHFFFAOYSA-N 2-bromoquinoline Chemical compound C1=CC=CC2=NC(Br)=CC=C21 QKJAZPHKNWSXDF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KIJXMUOJNZXYHU-UHFFFAOYSA-N n-propan-2-ylpropan-2-amine;hydrobromide Chemical compound [Br-].CC(C)[NH2+]C(C)C KIJXMUOJNZXYHU-UHFFFAOYSA-N 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/36—Oxalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22209/77A IT1078033B (it) | 1977-04-07 | 1977-04-07 | Processo per la preparazione di esteri dell'acido ossalico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781207L true NO781207L (no) | 1978-10-10 |
Family
ID=11193068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781207A NO781207L (no) | 1977-04-07 | 1978-04-05 | Fremgangsmaate for fremstilling av oksalsyreestere |
Country Status (37)
| Country | Link |
|---|---|
| US (1) | US4230881A (sv) |
| JP (1) | JPS53124215A (sv) |
| AR (1) | AR222793A1 (sv) |
| AT (1) | AT356638B (sv) |
| AU (1) | AU518170B2 (sv) |
| BE (1) | BE865812A (sv) |
| BG (1) | BG28568A3 (sv) |
| BR (1) | BR7802216A (sv) |
| CA (1) | CA1112662A (sv) |
| CH (1) | CH633516A5 (sv) |
| CS (1) | CS207595B2 (sv) |
| DD (1) | DD135719A5 (sv) |
| DE (1) | DE2814708C2 (sv) |
| DK (1) | DK153978A (sv) |
| EG (1) | EG13299A (sv) |
| ES (1) | ES469431A1 (sv) |
| FR (1) | FR2386513A1 (sv) |
| GB (1) | GB1583336A (sv) |
| GR (1) | GR63768B (sv) |
| HU (1) | HU180935B (sv) |
| IE (1) | IE46767B1 (sv) |
| IL (1) | IL54417A (sv) |
| IN (1) | IN148036B (sv) |
| IT (1) | IT1078033B (sv) |
| LU (1) | LU79397A1 (sv) |
| MW (1) | MW1178A1 (sv) |
| MX (1) | MX147280A (sv) |
| NL (1) | NL7803646A (sv) |
| NO (1) | NO781207L (sv) |
| PL (1) | PL118175B1 (sv) |
| PT (1) | PT67875B (sv) |
| RO (1) | RO75614A (sv) |
| SE (1) | SE7803853L (sv) |
| SU (1) | SU831070A3 (sv) |
| TR (1) | TR19773A (sv) |
| YU (1) | YU81278A (sv) |
| ZA (1) | ZA781866B (sv) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4614832A (en) * | 1979-12-17 | 1986-09-30 | Chevron Research Company | Dialkyl oxalates from carbon monoxide and an alcohol |
| JPS5867647A (ja) * | 1981-10-15 | 1983-04-22 | Ube Ind Ltd | マロン酸ジエステルの製造法 |
| US4523029A (en) * | 1982-06-15 | 1985-06-11 | Chevron Research Company | Oxidative carbonylation of alcohols to produce dialkyl oxalates |
| US4454342A (en) * | 1982-07-13 | 1984-06-12 | Atlantic Richfield Company | Preparation of dialkyl oxalates using a heterogeneous Pd-V-P catalyst for the oxidative carbonylation of alcohols |
| US4447638A (en) * | 1982-08-02 | 1984-05-08 | Atlantic Richfield Company | Preparation of dialkyl oxalates by the oxidative carbonylation of alcohols with a heterogeneous Pd-V-P-Ti containing catalyst system |
| US4451666A (en) * | 1982-08-06 | 1984-05-29 | Atlantic Richfield Company | Synthesis of oxalate esters by the oxidative carbonylation of alcohols with a heterogeneous manganese promoted Pd-V-P catalyst |
| US4447639A (en) * | 1982-08-06 | 1984-05-08 | Atlantic Richfield Company | Oxidative carbonylation of alcohols to dialkyl oxalates using a heterogeneous iron promoted Pd-V-P catalyst |
| DE3342291A1 (de) * | 1983-11-23 | 1985-05-30 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von oxalsaeurediestern |
| US4552976A (en) * | 1984-08-27 | 1985-11-12 | Texaco Inc. | Process for oxidative dicarbonylation of butadiene |
| US4554374A (en) * | 1984-08-27 | 1985-11-19 | Texaco Inc. | Process for dicarbonylation of simple olefins |
| DE3513255A1 (de) * | 1985-04-13 | 1986-10-23 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung von oxalsaeurediestern |
| US4629807A (en) * | 1986-02-06 | 1986-12-16 | Texaco Inc. | Selective synthesis of aliphatic dicarboxylic acid esters using palladium-phosphine or palladium-arsine catalysts |
| RU2493238C1 (ru) * | 2012-09-26 | 2013-09-20 | Государственное унитарное предприятие "Институт нефтехимпереработки Республики Башкортостан" (ГУП "ИНХП РБ") | Способ получения эфирной присадки к глубоко гидроочищенному дизельному топливу |
| WO2015184677A1 (zh) * | 2014-06-05 | 2015-12-10 | 上海戊正工程技术有限公司 | 工业合成气高压羰化生产草酸二甲酯并加氢制乙二醇的工艺和装置系统 |
| CN105330542A (zh) * | 2014-07-03 | 2016-02-17 | 中国石油化工股份有限公司 | 草酸二甲酯的生产方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3994960A (en) * | 1974-04-05 | 1976-11-30 | Ube Industries, Ltd. | Process for preparing dialkyl oxalates |
| US4005128A (en) * | 1975-04-02 | 1977-01-25 | Atlantic Richfield Company | Process for the preparation of oxalate esters |
| US4005129A (en) * | 1975-06-04 | 1977-01-25 | Atlantic Richfield Company | Process for the oxidative carbonylation of alcohols and method for the reoxidation of reduced copper salts produced by the oxidation carbonylation |
| JPS5315313A (en) * | 1976-07-27 | 1978-02-13 | Ube Ind Ltd | Production of oxalic acid diesters |
-
1977
- 1977-04-07 IT IT22209/77A patent/IT1078033B/it active
-
1978
- 1978-03-31 ZA ZA00781866A patent/ZA781866B/xx unknown
- 1978-04-03 GR GR55868A patent/GR63768B/el unknown
- 1978-04-03 IL IL54417A patent/IL54417A/xx unknown
- 1978-04-04 EG EG238/78A patent/EG13299A/xx active
- 1978-04-04 BG BG7839284A patent/BG28568A3/xx unknown
- 1978-04-05 AU AU34792/78A patent/AU518170B2/en not_active Expired
- 1978-04-05 DE DE2814708A patent/DE2814708C2/de not_active Expired
- 1978-04-05 TR TR19773A patent/TR19773A/xx unknown
- 1978-04-05 NO NO781207A patent/NO781207L/no unknown
- 1978-04-05 IN IN372/CAL/78A patent/IN148036B/en unknown
- 1978-04-05 SE SE7803853A patent/SE7803853L/sv unknown
- 1978-04-05 NL NL7803646A patent/NL7803646A/xx not_active Application Discontinuation
- 1978-04-05 AR AR271700A patent/AR222793A1/es active
- 1978-04-06 AT AT243378A patent/AT356638B/de not_active IP Right Cessation
- 1978-04-06 FR FR7810270A patent/FR2386513A1/fr active Granted
- 1978-04-06 US US05/894,139 patent/US4230881A/en not_active Expired - Lifetime
- 1978-04-06 CS CS782250A patent/CS207595B2/cs unknown
- 1978-04-06 MX MX173031A patent/MX147280A/es unknown
- 1978-04-06 CH CH373478A patent/CH633516A5/it not_active IP Right Cessation
- 1978-04-06 GB GB13590/78A patent/GB1583336A/en not_active Expired
- 1978-04-06 HU HU78SA3105A patent/HU180935B/hu unknown
- 1978-04-06 CA CA300,624A patent/CA1112662A/en not_active Expired
- 1978-04-06 PT PT67875A patent/PT67875B/pt unknown
- 1978-04-06 DK DK153978A patent/DK153978A/da not_active IP Right Cessation
- 1978-04-07 LU LU79397A patent/LU79397A1/xx unknown
- 1978-04-07 JP JP4043678A patent/JPS53124215A/ja active Pending
- 1978-04-07 RO RO7893746A patent/RO75614A/ro unknown
- 1978-04-07 BE BE186660A patent/BE865812A/xx not_active IP Right Cessation
- 1978-04-07 DD DD78204657A patent/DD135719A5/xx unknown
- 1978-04-07 PL PL1978205895A patent/PL118175B1/pl unknown
- 1978-04-07 IE IE692/78A patent/IE46767B1/en unknown
- 1978-04-07 BR BR7802216A patent/BR7802216A/pt unknown
- 1978-04-07 MW MW11/78A patent/MW1178A1/xx unknown
- 1978-04-07 SU SU782603198A patent/SU831070A3/ru active
- 1978-04-07 ES ES469431A patent/ES469431A1/es not_active Expired
- 1978-04-15 YU YU00812/78A patent/YU81278A/xx unknown
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