CA1225658A - Production of formate salts - Google Patents
Production of formate saltsInfo
- Publication number
- CA1225658A CA1225658A CA000471921A CA471921A CA1225658A CA 1225658 A CA1225658 A CA 1225658A CA 000471921 A CA000471921 A CA 000471921A CA 471921 A CA471921 A CA 471921A CA 1225658 A CA1225658 A CA 1225658A
- Authority
- CA
- Canada
- Prior art keywords
- nitrogen atom
- tertiary nitrogen
- nitrogenous base
- rhodium
- base containing
- 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
- 150000004675 formic acid derivatives Chemical class 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 36
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 18
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052703 rhodium Inorganic materials 0.000 claims abstract description 16
- 239000010948 rhodium Substances 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 150000002903 organophosphorus compounds Chemical class 0.000 claims abstract description 5
- 150000002484 inorganic compounds Chemical class 0.000 claims abstract description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000005270 trialkylamine group Chemical group 0.000 claims description 5
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 5
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000003333 secondary alcohols Chemical class 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 26
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 27
- 239000002585 base Substances 0.000 description 14
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- -1 Trialkylammonium formates Chemical class 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 6
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 6
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000005208 trialkylammonium group Chemical group 0.000 description 2
- RVNSAAIWCWTCTJ-ZPQYLTHOSA-N (2s,3s,4r)-2-(1,2-dihydroxyethyl)pyrrolidine-3,4-diol Chemical compound OCC(O)[C@@H]1NC[C@@H](O)[C@H]1O RVNSAAIWCWTCTJ-ZPQYLTHOSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- 101150058765 BACE1 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- 101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- DYWODRJVMZCPDO-UHFFFAOYSA-N ethylammonium formate Chemical compound CC[NH3+].[O-]C=O DYWODRJVMZCPDO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848401005A GB8401005D0 (en) | 1984-01-14 | 1984-01-14 | Formate salts |
| GB8401005 | 1984-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1225658A true CA1225658A (en) | 1987-08-18 |
Family
ID=10555008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000471921A Expired CA1225658A (en) | 1984-01-14 | 1985-01-11 | Production of formate salts |
Country Status (6)
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68920933T2 (de) * | 1988-08-20 | 1995-05-24 | Bp Chem Int Ltd | Produktion von Formiat-Salzen von Stickstoffbasen. |
| DE4211141A1 (de) * | 1992-04-03 | 1993-10-07 | Basf Ag | Verfahren zur Herstellung von Ameisensäure durch thermische Spaltung von quartären Ammoniumformiaten |
| DE102004040789A1 (de) | 2004-08-23 | 2006-03-02 | Basf Ag | Verfahren zur Herstellung von Ameisensäure |
| JP4822253B2 (ja) * | 2005-08-23 | 2011-11-24 | 独立行政法人産業技術総合研究所 | 二酸化炭素と水素からギ酸塩の製造方法 |
| EP2445860B1 (de) * | 2009-06-26 | 2013-05-29 | Basf Se | Verfahren zur herstellung von ameisensäure |
| UA104324C2 (ru) | 2009-06-26 | 2014-01-27 | Басф Се | Способ получения муравьиной кислоты |
| US9945040B2 (en) | 2010-07-04 | 2018-04-17 | Dioxide Materials, Inc. | Catalyst layers and electrolyzers |
| US8956990B2 (en) | 2010-03-26 | 2015-02-17 | Dioxide Materials, Inc. | Catalyst mixtures |
| US9181625B2 (en) | 2010-03-26 | 2015-11-10 | Dioxide Materials, Inc. | Devices and processes for carbon dioxide conversion into useful fuels and chemicals |
| US9790161B2 (en) | 2010-03-26 | 2017-10-17 | Dioxide Materials, Inc | Process for the sustainable production of acrylic acid |
| US9957624B2 (en) | 2010-03-26 | 2018-05-01 | Dioxide Materials, Inc. | Electrochemical devices comprising novel catalyst mixtures |
| US9193593B2 (en) | 2010-03-26 | 2015-11-24 | Dioxide Materials, Inc. | Hydrogenation of formic acid to formaldehyde |
| US9815021B2 (en) | 2010-03-26 | 2017-11-14 | Dioxide Materials, Inc. | Electrocatalytic process for carbon dioxide conversion |
| US10173169B2 (en) | 2010-03-26 | 2019-01-08 | Dioxide Materials, Inc | Devices for electrocatalytic conversion of carbon dioxide |
| US20110237830A1 (en) * | 2010-03-26 | 2011-09-29 | Dioxide Materials Inc | Novel catalyst mixtures |
| US9566574B2 (en) | 2010-07-04 | 2017-02-14 | Dioxide Materials, Inc. | Catalyst mixtures |
| US9012345B2 (en) | 2010-03-26 | 2015-04-21 | Dioxide Materials, Inc. | Electrocatalysts for carbon dioxide conversion |
| US8791297B2 (en) | 2010-06-29 | 2014-07-29 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| CA2774151A1 (en) * | 2010-06-29 | 2012-01-05 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| US8877965B2 (en) | 2010-06-29 | 2014-11-04 | Basf Se | Process for preparing formic acid by reaction of carbon dioxide with hydrogen |
| RU2013103599A (ru) | 2010-06-29 | 2014-08-10 | Басф Се | Способ получения муравьиной кислоты в результате взаимодействия диоксида углерода с водородом |
| WO2012034991A1 (de) | 2010-09-17 | 2012-03-22 | Basf Se | Verfahren zur herstellung von formamiden |
| BR112013015395A2 (pt) | 2010-12-21 | 2016-09-20 | Basf Se | processo para preparar ácido fórmico |
| US8742171B2 (en) | 2011-06-09 | 2014-06-03 | Basf Se | Process for preparing formic acid |
| WO2012168396A1 (en) | 2011-06-09 | 2012-12-13 | Basf Se | Process for preparing formic acid |
| CN103649036A (zh) | 2011-07-07 | 2014-03-19 | 巴斯夫欧洲公司 | 通过使二氧化碳与氢气反应制备甲酸的方法 |
| DE102012014159A1 (de) | 2011-07-27 | 2013-01-31 | Basf Se | Verfahren zur Herstellung von Methylformiat |
| US20130090496A1 (en) * | 2011-10-07 | 2013-04-11 | Basf Se | Process for preparing formic acid by reacting carbon dioxide with hydrogen |
| SG11201401103YA (en) * | 2011-11-10 | 2014-08-28 | Basf Se | Process for the preparation of formic acid by reaction of carbon dioxide with hydrogen |
| EP2858970A1 (en) | 2012-06-11 | 2015-04-15 | Basf Se | Process for preparing formic acid |
| US10647652B2 (en) | 2013-02-24 | 2020-05-12 | Dioxide Materials, Inc. | Process for the sustainable production of acrylic acid |
| US10774431B2 (en) | 2014-10-21 | 2020-09-15 | Dioxide Materials, Inc. | Ion-conducting membranes |
| US10975480B2 (en) | 2015-02-03 | 2021-04-13 | Dioxide Materials, Inc. | Electrocatalytic process for carbon dioxide conversion |
| US10396329B2 (en) | 2017-05-01 | 2019-08-27 | Dioxide Materials, Inc. | Battery separator membrane and battery employing same |
| EP3936498A4 (en) * | 2019-03-08 | 2022-12-14 | Nitto Denko Corporation | PROCESS FOR THE PRODUCTION OF FORMIC ACID |
| JP7405594B2 (ja) * | 2019-03-08 | 2023-12-26 | 日東電工株式会社 | ギ酸の製造方法 |
| EP4089177A1 (en) | 2021-05-14 | 2022-11-16 | Cebal - Centro De Biotecnologia Agrícola E Agro-Alimentar Do Alentejo | Process for the production of formic acid using e. coli strains |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1019230A (en) * | 1911-02-06 | 1912-03-05 | Le Camphre Soc | Manufacture of formates. |
| US3959386A (en) * | 1974-05-13 | 1976-05-25 | Universal Oil Products Company | Production of primary compounds |
| CA1220222A (en) * | 1982-05-22 | 1987-04-07 | David J. Drury | Production of formate salts |
-
1984
- 1984-01-14 GB GB848401005A patent/GB8401005D0/en active Pending
-
1985
- 1985-01-08 DE DE8585300112T patent/DE3560412D1/de not_active Expired
- 1985-01-08 EP EP85300112A patent/EP0151510B1/en not_active Expired
- 1985-01-11 CA CA000471921A patent/CA1225658A/en not_active Expired
- 1985-01-14 JP JP60004834A patent/JPS60209260A/ja active Granted
-
1988
- 1988-04-07 US US07/180,672 patent/US4879070A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4879070A (en) | 1989-11-07 |
| GB8401005D0 (en) | 1984-02-15 |
| DE3560412D1 (en) | 1987-09-10 |
| JPS60209260A (ja) | 1985-10-21 |
| EP0151510B1 (en) | 1987-08-05 |
| EP0151510A1 (en) | 1985-08-14 |
| JPH0533694B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |