DE69602302T2 - Integriertes Epoxidationsverfahren - Google Patents
Integriertes EpoxidationsverfahrenInfo
- Publication number
- DE69602302T2 DE69602302T2 DE69602302T DE69602302T DE69602302T2 DE 69602302 T2 DE69602302 T2 DE 69602302T2 DE 69602302 T DE69602302 T DE 69602302T DE 69602302 T DE69602302 T DE 69602302T DE 69602302 T2 DE69602302 T2 DE 69602302T2
- Authority
- DE
- Germany
- Prior art keywords
- stream
- methanol
- hydrogen peroxide
- alcohol
- process according
- 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 - Fee Related
Links
- 238000006735 epoxidation reaction Methods 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 180
- 150000003333 secondary alcohols Chemical class 0.000 claims abstract description 51
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 47
- 230000003647 oxidation Effects 0.000 claims abstract description 45
- 150000002576 ketones Chemical class 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- 150000001336 alkenes Chemical class 0.000 claims abstract description 33
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000010936 titanium Substances 0.000 claims abstract description 28
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 27
- 239000003085 diluting agent Substances 0.000 claims abstract description 22
- 238000000926 separation method Methods 0.000 claims abstract description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 129
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 150000002924 oxiranes Chemical class 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 17
- 238000004821 distillation Methods 0.000 claims description 15
- 238000005984 hydrogenation reaction Methods 0.000 claims description 15
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910021536 Zeolite Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 239000000011 acetone peroxide Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000006227 byproduct Substances 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- -1 aliphatic ketone peroxide Chemical class 0.000 description 7
- 230000001590 oxidative effect Effects 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 238000004508 fractional distillation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/404,657 US5693834A (en) | 1995-03-15 | 1995-03-15 | Integrated process for epoxidation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69602302D1 DE69602302D1 (de) | 1999-06-10 |
| DE69602302T2 true DE69602302T2 (de) | 1999-10-14 |
Family
ID=23600502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69602302T Expired - Fee Related DE69602302T2 (de) | 1995-03-15 | 1996-03-11 | Integriertes Epoxidationsverfahren |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5693834A (enExample) |
| EP (1) | EP0732327B1 (enExample) |
| JP (1) | JPH08245604A (enExample) |
| KR (1) | KR100385627B1 (enExample) |
| CN (1) | CN1138039A (enExample) |
| AT (1) | ATE179705T1 (enExample) |
| CA (1) | CA2170557A1 (enExample) |
| DE (1) | DE69602302T2 (enExample) |
| ES (1) | ES2133898T3 (enExample) |
| IN (1) | IN187024B (enExample) |
| RU (1) | RU2168504C2 (enExample) |
| SG (1) | SG43937A1 (enExample) |
| TW (1) | TW333530B (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19623611A1 (de) * | 1996-06-13 | 1997-12-18 | Basf Ag | Verfahren zur Herstellung von Epoxiden aus Olefinen und Wasserstoffperoxid |
| BE1010716A3 (fr) * | 1996-10-25 | 1998-12-01 | Solvay | Procede de regeneration de catalyseurs de type silicalite au titane. |
| US6024840A (en) * | 1997-08-08 | 2000-02-15 | Arco Chemical Technology, L.P. | Propylene oxide purification |
| US5863391A (en) * | 1997-08-15 | 1999-01-26 | Arco Chemical Technology, L.P. | Purification of a methanol stream |
| US5849938A (en) * | 1997-09-02 | 1998-12-15 | Arco Chemical Technology, L.P. | Separation of methanol and propylene oxide from a reaction mixture |
| DE69806155T2 (de) * | 1998-03-26 | 2003-02-06 | Repsol Quimica S.A., Madrid | Verfahren zur epoxidierung von olefinen mit wasserstoffperoxid |
| EP1074548B1 (en) * | 1999-08-06 | 2006-01-11 | Repsol Quimica S.A. | A method for continuous production of propylene oxide and other alkene oxides |
| US6337412B1 (en) * | 2000-04-25 | 2002-01-08 | Chemical Research & Licensing Company | Three stage propylene oxide process |
| DE10032885A1 (de) * | 2000-07-06 | 2002-01-17 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| DE10032884A1 (de) * | 2000-07-06 | 2002-01-24 | Basf Ag | Verfahren zur Herstellung von Propylenoxid |
| EP1359148A1 (en) * | 2002-05-02 | 2003-11-05 | Degussa AG | Process for the epoxidation of olefins |
| KR101363833B1 (ko) * | 2005-12-27 | 2014-02-14 | 바스프 에스이 | 프로펜의 에폭시화 방법 |
| KR100907713B1 (ko) * | 2007-09-28 | 2009-07-14 | 영 수 문 | 정수장치 |
| WO2009041751A1 (en) * | 2007-09-28 | 2009-04-02 | Young-Soo Moon | Device for purifying water |
| JP5593686B2 (ja) * | 2009-11-30 | 2014-09-24 | 東ソー株式会社 | エポキシ化合物及びケトン化合物の同時製造方法 |
| JP5655470B2 (ja) * | 2010-09-29 | 2015-01-21 | 東ソー株式会社 | エポキシ化合物の製造方法 |
| JP5655476B2 (ja) * | 2010-09-30 | 2015-01-21 | 東ソー株式会社 | エポキシ化合物の製造方法 |
| JP5655483B2 (ja) * | 2010-10-06 | 2015-01-21 | 東ソー株式会社 | エポキシ化合物の製造法 |
| CN109529927A (zh) * | 2019-01-06 | 2019-03-29 | 福州大学 | 一种丙烯气相环氧化催化剂及其制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953362A (en) * | 1975-04-30 | 1976-04-27 | Olin Corporation | Molybdenum salt catalysts and methods of preparing them |
| US4009122A (en) * | 1975-06-23 | 1977-02-22 | Olin Corporation | Novel glycol soluble molybdenum catalysts and method of preparation |
| US4157346A (en) * | 1976-10-21 | 1979-06-05 | Olin Corporation | Catalytic epoxidation of alkylene compounds |
| IT1152299B (it) * | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'espossidazione di composti olefinici |
| SU1171458A1 (ru) * | 1983-02-14 | 1985-08-07 | Днепропетровский Ордена Трудового Красного Знамени Государственный Университет Им.300-Летия Воссоединения Украины С Россией | Способ получени эпоксициклододекадиена-5,9 |
| DE3780476T2 (de) * | 1986-01-28 | 1992-12-17 | Enichem Sintesi | Verfahren zur epoxydation von olefinischen verbindungen. |
| IT1250756B (it) * | 1991-08-02 | 1995-04-21 | Eniricerche Spa | Procedimento per la produzione di ossidi olefinici |
| EP0549013B1 (en) * | 1991-11-26 | 1996-07-17 | ENIRICERCHE S.p.A. | Process for oxidizing organic compounds with hydrogen peroxide produced in an anthraquinone redox process |
| US5262550A (en) * | 1992-04-30 | 1993-11-16 | Arco Chemical Technology, L.P. | Epoxidation process using titanium-rich silicalite catalysts |
| US5214168A (en) * | 1992-04-30 | 1993-05-25 | Arco Chemical Technology, L.P. | Integrated process for epoxide production |
| US5354875A (en) * | 1993-12-23 | 1994-10-11 | Uop | Epoxidation of olefins using a titania-supported titanosilicate |
| US5374747A (en) * | 1993-12-23 | 1994-12-20 | Arco Chemical Technology, L.P. | Epoxidation process and catalyst therefore |
| US5412122A (en) * | 1993-12-23 | 1995-05-02 | Arco Chemical Technology, L.P. | Epoxidation process |
| US5384418A (en) * | 1994-01-25 | 1995-01-24 | Arco Chemical Technology, L.P. | Integrated process for epoxide production |
-
1995
- 1995-03-15 US US08/404,657 patent/US5693834A/en not_active Expired - Fee Related
-
1996
- 1996-02-26 IN IN335CA1996 patent/IN187024B/en unknown
- 1996-02-27 SG SG1996006128A patent/SG43937A1/en unknown
- 1996-02-28 CA CA002170557A patent/CA2170557A1/en not_active Abandoned
- 1996-03-01 JP JP8068912A patent/JPH08245604A/ja not_active Ceased
- 1996-03-11 DE DE69602302T patent/DE69602302T2/de not_active Expired - Fee Related
- 1996-03-11 ES ES96301645T patent/ES2133898T3/es not_active Expired - Lifetime
- 1996-03-11 AT AT96301645T patent/ATE179705T1/de not_active IP Right Cessation
- 1996-03-11 EP EP96301645A patent/EP0732327B1/en not_active Expired - Lifetime
- 1996-03-12 KR KR1019960006472A patent/KR100385627B1/ko not_active Expired - Fee Related
- 1996-03-14 RU RU96104554/04A patent/RU2168504C2/ru active
- 1996-03-15 CN CN96103129A patent/CN1138039A/zh active Pending
- 1996-03-15 TW TW085103118A patent/TW333530B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| ES2133898T3 (es) | 1999-09-16 |
| TW333530B (en) | 1998-06-11 |
| US5693834A (en) | 1997-12-02 |
| EP0732327B1 (en) | 1999-05-06 |
| CN1138039A (zh) | 1996-12-18 |
| ATE179705T1 (de) | 1999-05-15 |
| RU2168504C2 (ru) | 2001-06-10 |
| DE69602302D1 (de) | 1999-06-10 |
| EP0732327A1 (en) | 1996-09-18 |
| JPH08245604A (ja) | 1996-09-24 |
| SG43937A1 (en) | 1997-11-14 |
| CA2170557A1 (en) | 1996-09-16 |
| KR100385627B1 (ko) | 2003-08-21 |
| KR960034191A (ko) | 1996-10-22 |
| IN187024B (enExample) | 2001-12-29 |
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