CA2411070C - Process for operating the epoxidation of ethylene with supported silver catalysts - Google Patents
Process for operating the epoxidation of ethylene with supported silver catalysts Download PDFInfo
- Publication number
- CA2411070C CA2411070C CA2411070A CA2411070A CA2411070C CA 2411070 C CA2411070 C CA 2411070C CA 2411070 A CA2411070 A CA 2411070A CA 2411070 A CA2411070 A CA 2411070A CA 2411070 C CA2411070 C CA 2411070C
- Authority
- CA
- Canada
- Prior art keywords
- ethylene
- catalyst
- ethylene oxide
- concentration
- operation phase
- 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 - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 140
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 239000005977 Ethylene Substances 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 50
- 230000008569 process Effects 0.000 title claims abstract description 46
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 19
- 239000004332 silver Substances 0.000 title claims abstract description 19
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000006735 epoxidation reaction Methods 0.000 title description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 73
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 45
- 239000001301 oxygen Substances 0.000 claims abstract description 45
- 239000012071 phase Substances 0.000 claims abstract description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 19
- 239000011541 reaction mixture Substances 0.000 claims abstract description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 14
- 230000003647 oxidation Effects 0.000 claims abstract description 13
- 230000001186 cumulative effect Effects 0.000 claims abstract description 12
- 239000012808 vapor phase Substances 0.000 claims abstract description 7
- 239000007789 gas Substances 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 26
- 229910052702 rhenium Inorganic materials 0.000 claims description 17
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 230000001737 promoting effect Effects 0.000 claims description 6
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 4
- 229960003750 ethyl chloride Drugs 0.000 claims description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052776 Thorium Inorganic materials 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 239000010937 tungsten Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- 239000001569 carbon dioxide Substances 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 11
- -1 1,2-ethanediol ethers Chemical class 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000011261 inert gas Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012495 reaction gas Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000000180 1,2-diols Chemical class 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000013022 venting Methods 0.000 description 2
- RGZSQWQPBWRIAQ-HUUCEWRRSA-N (2r)-6-methyl-2-[(1s)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol Chemical compound CC(C)=CCC[C@@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-HUUCEWRRSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003716 rejuvenation Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/66—Silver or gold
- B01J23/68—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/688—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with manganese, technetium or rhenium
-
- 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
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
-
- 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
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Epoxy Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59152500A | 2000-06-09 | 2000-06-09 | |
| US09/591,525 | 2000-06-09 | ||
| US09/735,360 | 2000-12-12 | ||
| US09/735,360 US6372925B1 (en) | 2000-06-09 | 2000-12-12 | Process for operating the epoxidation of ethylene |
| PCT/US2001/018097 WO2001096324A2 (en) | 2000-06-09 | 2001-06-05 | Process for operating the epoxidation of ethylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2411070A1 CA2411070A1 (en) | 2001-12-20 |
| CA2411070C true CA2411070C (en) | 2010-08-10 |
Family
ID=27081174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2411070A Expired - Lifetime CA2411070C (en) | 2000-06-09 | 2001-06-05 | Process for operating the epoxidation of ethylene with supported silver catalysts |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US6372925B1 (OSRAM) |
| EP (1) | EP1292587B1 (OSRAM) |
| JP (1) | JP5097325B2 (OSRAM) |
| KR (1) | KR100827473B1 (OSRAM) |
| CN (1) | CN1217941C (OSRAM) |
| AT (1) | ATE342259T1 (OSRAM) |
| AU (1) | AU2001266704A1 (OSRAM) |
| BR (1) | BR0111475B1 (OSRAM) |
| CA (1) | CA2411070C (OSRAM) |
| DE (1) | DE60123788T2 (OSRAM) |
| ES (1) | ES2269421T3 (OSRAM) |
| GC (1) | GC0000430A (OSRAM) |
| IN (1) | IN2002DE01165A (OSRAM) |
| MX (1) | MXPA02012036A (OSRAM) |
| MY (1) | MY128386A (OSRAM) |
| RU (1) | RU2263670C2 (OSRAM) |
| TW (1) | TWI230707B (OSRAM) |
| WO (1) | WO2001096324A2 (OSRAM) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6372925B1 (en) * | 2000-06-09 | 2002-04-16 | Shell Oil Company | Process for operating the epoxidation of ethylene |
| US7193094B2 (en) * | 2001-11-20 | 2007-03-20 | Shell Oil Company | Process and systems for the epoxidation of an olefin |
| WO2004002971A1 (en) * | 2002-06-28 | 2004-01-08 | Shell Internationale Research Maatschappij B.V. | A method for the start-up of an epoxidation process, a catalyst and a process for the epoxidation of an olefin |
| WO2004002972A2 (en) * | 2002-06-28 | 2004-01-08 | Shell Internationale Research Maatschappij B.V. | A method for the start-up of an epoxidation process and a process for the epoxidation of an olefin |
| BR0312244B1 (pt) * | 2002-06-28 | 2013-06-25 | mÉtodo para melhorar a seletividade de um catalisador e um processo para a epoxidaÇço de uma olefina | |
| US20040110973A1 (en) * | 2002-10-28 | 2004-06-10 | Marek Matusz | Olefin oxide catalysts |
| MY136774A (en) * | 2003-02-28 | 2008-11-28 | Shell Int Research | Method of improving the operation of a manufacturing process |
| MY153179A (en) * | 2003-02-28 | 2015-01-29 | Shell Int Research | A method of manufacturing ethylene oxide |
| MY146505A (en) * | 2003-02-28 | 2012-08-15 | Shell Int Research | A method of manufacturing ethylene oxide |
| TWI346574B (en) | 2003-03-31 | 2011-08-11 | Shell Int Research | A catalyst composition, a process for preparing the catalyst composition and a use of the catalyst composition |
| JP2006522138A (ja) * | 2003-04-01 | 2006-09-28 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | オレフィンのエポキシ化方法とその方法において使用される触媒 |
| US7348444B2 (en) * | 2003-04-07 | 2008-03-25 | Shell Oil Company | Process for the production of an olefin oxide |
| US6858560B2 (en) | 2003-04-23 | 2005-02-22 | Scientific Design Co., Inc. | Ethylene oxide catalyst |
| MX260863B (es) | 2003-05-07 | 2008-09-26 | Shell Int Research | Catalizadores que contienen plata, su elaboracion y uso de los mismos. |
| US20040225138A1 (en) * | 2003-05-07 | 2004-11-11 | Mcallister Paul Michael | Reactor system and process for the manufacture of ethylene oxide |
| US8148555B2 (en) * | 2003-06-26 | 2012-04-03 | Shell Oil Company | Method for improving the selectivity of a catalyst and a process for the epoxidation of an olefin |
| TW200602123A (en) * | 2004-04-01 | 2006-01-16 | Shell Int Research | Process for preparing a catalyst, the catalyst, and a use of the catalyst |
| US8536083B2 (en) | 2004-09-01 | 2013-09-17 | Shell Oil Company | Olefin epoxidation process, a catalyst for use in the process, a carrier for use in preparing the catalyst, and a process for preparing the carrier |
| EP2617488A3 (en) | 2004-09-01 | 2014-01-22 | Shell Internationale Research Maatschappij B.V. | Process for preparing a catalyst for use in an olefin epoxidation process and epoxidation process using the catalyst |
| RU2007115405A (ru) * | 2004-09-24 | 2008-10-27 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (NL) | Способ выбора формированных частиц, способ сборки системы, способ реагирования газообразного сырья в такой системе, компьютерный программный продукт и компьютерная система |
| CN101160298B (zh) * | 2005-02-25 | 2011-06-22 | 住友化学株式会社 | 环氧烷烃的制备方法 |
| WO2006102189A1 (en) * | 2005-03-22 | 2006-09-28 | Shell Internationale Research Maatschappij B.V. | A reactor system and process for the manufacture of ethylene oxide |
| BRPI0611676B1 (pt) | 2005-06-07 | 2015-08-11 | Shell Int Research | Catalisador, processo para a preparação do catalisador, e processo para a produção de um óxido de olefina, um 1,2- diol, e um 1,2-diol éter e uma alcanolamina |
| US7750170B2 (en) | 2005-12-22 | 2010-07-06 | Shell Oil Company | Process for mixing an oxidant having explosive potential with a hydrocarbon |
| TW200734317A (en) * | 2005-12-22 | 2007-09-16 | Shell Int Research | A process for the preparation of an olefin oxide or a chemical derivable from an olefin oxide |
| US7459589B2 (en) | 2005-12-22 | 2008-12-02 | Shell Oil Company | Process for the preparation of an alkylene glycol |
| TW200738332A (en) * | 2006-02-03 | 2007-10-16 | Shell Int Research | A process for treating a catalyst, the catalyst, and use of the catalyst |
| BRPI0707608A2 (pt) * | 2006-02-10 | 2011-05-10 | Shell Int Research | processo para preparar um catalisador, o catalisador, e um processo para a produÇço de àxido de olefina, 1,2-diol,1,2-diol Éter, ou alcanolamina |
| US7553795B2 (en) * | 2006-03-21 | 2009-06-30 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Activation of high selectivity ethylene oxide catalyst |
| US20090270640A1 (en) * | 2006-04-21 | 2009-10-29 | Basf Aktiengesellschaft | Method for production of ethylene oxide in a microchannel reactor |
| US8097557B2 (en) * | 2006-08-08 | 2012-01-17 | Sd Lizenverwertungsgesellschaft Mbh & Co. Kg | Two-stage calcination for catalyst production |
| MX2009002309A (es) * | 2006-09-01 | 2009-03-20 | Dow Global Technologies Inc | Control mejorado y optimizacion de proceso para hacer oxido de etileno. |
| US7977274B2 (en) * | 2006-09-29 | 2011-07-12 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Catalyst with bimodal pore size distribution and the use thereof |
| AR066468A1 (es) * | 2007-05-09 | 2009-08-19 | Shell Int Research | Un catalizador de epoxidacion, un proceso para preparar el mismo, y un proceso para producir un oxido de olefina , un 1,2- diol, un 1,2 - diol eter, un 1,2- carbonato, o una alcanolamina |
| JP5889528B2 (ja) * | 2007-05-09 | 2016-03-22 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | エポキシ化触媒、触媒を調製するための方法および酸化オレフィン、１，２−ジオール、１，２−ジオールエーテル、１，２−カーボネートまたはアルカノールアミンを製造する方法。 |
| EP2155708B1 (en) | 2007-05-09 | 2018-02-21 | Shell Internationale Research Maatschappij B.V. | A process for the production of an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate, or an alkanolamine |
| WO2008144396A2 (en) * | 2007-05-18 | 2008-11-27 | Shell Oil Company | A reactor system, and a process for preparing an olefin oxide, a 1,2-diol, a 1,2-diol ether, a 1,2-carbonate and an alkanolamine |
| US9144765B2 (en) | 2007-05-18 | 2015-09-29 | Shell Oil Company | Reactor system, an absorbent and a process for reacting a feed |
| CA2686852A1 (en) | 2007-05-18 | 2008-11-27 | Shell Internationale Research Maatschappij B.V. | A reactor system, an absorbent and a process for reacting a feed |
| US8290626B2 (en) * | 2007-09-10 | 2012-10-16 | SD Lizenzverwertungsgesellschadt mbH & Co KG | Chemical process optimization method that considers chemical process plant safety |
| US7803957B2 (en) * | 2007-09-11 | 2010-09-28 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Ethylene oxide production using fixed moderator concentration |
| DE102008011767B4 (de) | 2008-02-28 | 2012-07-26 | Basf Se | Verfahren zur Herstellung von olefinisch ungesättigten Carbonylverbindungen durch oxidative Dehydrierung von Alkoholen |
| DE102008014910A1 (de) | 2008-03-19 | 2009-09-24 | Basf Se | Verwendung eines geträgerten edelmetallhaltigen Katalysators zur oxidativen Dehydrierung |
| US7763096B2 (en) * | 2008-05-06 | 2010-07-27 | Sd Lizenzverwertungsgesellschaft Mbh & Co. Kg | Recovery of rhenium |
| KR101629037B1 (ko) | 2008-05-07 | 2016-06-09 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 에폭시화 방법의 스타트업 방법, 산화에틸렌, 1,2-디올, 1,2-디올 에테르, 1,2-카보네이트 또는 알칸올아민의 생산방법 |
| CN102066348B (zh) * | 2008-05-07 | 2013-09-25 | 国际壳牌研究有限公司 | 环氧烷、1，2-二醇、1，2-二醇醚、1，2-碳酸酯或链烷醇胺的制备方法 |
| JP2011520895A (ja) | 2008-05-15 | 2011-07-21 | シエル・インターナシヨナル・リサーチ・マートスハツペイ・ベー・ヴエー | アルキレンカーボネートおよび／またはアルキレングリコールの調製のための方法 |
| CN102066352B (zh) * | 2008-05-15 | 2014-03-19 | 国际壳牌研究有限公司 | 制备亚烷基碳酸酯和亚烷基二醇的方法 |
| DE102008025835A1 (de) * | 2008-05-29 | 2009-12-03 | Bayer Technology Services Gmbh | Verfahren zur Herstellung von Ethylenoxid |
| WO2009150208A1 (en) * | 2008-06-13 | 2009-12-17 | Shell Internationale Research Maatschappij B.V. | Method for measuring the selectivity of a process for the production of ethylene oxide |
| US8933254B2 (en) * | 2008-07-14 | 2015-01-13 | Basf Se | Process for making ethylene oxide |
| CA2730550A1 (en) * | 2008-07-14 | 2010-01-21 | Velocys Inc. | Process for making ethylene oxide using microchannel process technology |
| US8349765B2 (en) | 2008-07-18 | 2013-01-08 | Scientific Design Company, Inc. | Mullite-containing carrier for ethylene oxide catalysts |
| US8524927B2 (en) | 2009-07-13 | 2013-09-03 | Velocys, Inc. | Process for making ethylene oxide using microchannel process technology |
| RU2547146C2 (ru) * | 2009-11-10 | 2015-04-10 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Способ получения этиленоксида |
| JP2012522061A (ja) | 2009-12-28 | 2012-09-20 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | アルキレンオキサイドの製造における銀触媒上への塩化銀の生成の制御方法 |
| WO2012050819A1 (en) | 2010-09-29 | 2012-04-19 | Shell Oil Company | Improved eo process control |
| US8742146B2 (en) | 2010-12-08 | 2014-06-03 | Shell Oil Company | Process for improving the selectivity of an EO catalyst |
| US8742147B2 (en) | 2010-12-08 | 2014-06-03 | Shell Oil Company | Process for improving the selectivity of an EO catalyst |
| US8884037B2 (en) | 2010-12-10 | 2014-11-11 | Dow Technology Investments Llc | Method of reducing the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst |
| EP2651908B1 (en) * | 2010-12-15 | 2016-02-24 | Dow Technology Investments LLC | Method of starting-up a process of producing an alkylene oxide using a high-efficiency catalyst |
| CN102558099B (zh) * | 2010-12-29 | 2014-11-12 | 中国石油化工股份有限公司 | 由乙烯生产环氧乙烷的方法 |
| KR102027597B1 (ko) | 2011-04-29 | 2019-10-01 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | Ｅｏ 촉매의 선택성 개선 방법 |
| US9181207B2 (en) | 2011-12-09 | 2015-11-10 | Dow Technology Investments Llc | Method of reducing or maintaining the value of an alkylene oxide production parameter in a process of making an alkylene oxide using a high efficiency catalyst |
| FR3001968B1 (fr) * | 2013-02-12 | 2015-02-27 | IFP Energies Nouvelles | Procede de production d'oxyde d'ethylene a partir d'un flux d'ethanol thermo-mecaniquement integre |
| CN104888855B (zh) * | 2015-04-03 | 2017-03-01 | 江南大学 | 一种用于烯烃环氧化反应的乙酰丙酮氧钼固体催化剂及其制备方法 |
| KR20230027318A (ko) * | 2016-08-09 | 2023-02-27 | 사이언티픽 디자인 컴파니 인코포레이티드 | 글리콜 에테르 제조 방법 |
| KR102449657B1 (ko) | 2016-12-02 | 2022-09-29 | 쉘 인터내셔날 리써취 마트샤피지 비.브이. | 에틸렌 에폭시화 촉매를 컨디셔닝하는 방법 및 에틸렌 옥사이드의 생산을 위한 관련된 방법 |
| US11059017B2 (en) | 2017-09-15 | 2021-07-13 | MultiPhase Solutions, Inc. | Halogen selective detection gas chromatography for the on-line analysis and control of selective oxidation chemical production processes |
| TWI801461B (zh) * | 2017-12-08 | 2023-05-11 | 荷蘭商蜆殼國際研究所 | 用於製備碳酸伸乙酯及乙二醇之製程 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1191983A (en) | 1968-04-11 | 1970-05-13 | Sir Soc Italiana Resine Spa | Preparation of Ethylene Oxide |
| US3960775A (en) | 1969-08-26 | 1976-06-01 | Snam Progetti S.P.A. | Catalyst for the production of ethylene oxide |
| GB1319004A (en) * | 1971-07-13 | 1973-05-31 | Nippon Catalytic Chem Ind | Process for preparing ethylene oxide |
| IT972792B (it) * | 1972-12-22 | 1974-05-31 | Sir Soc Italiana Resine Spa | Procedimento per la preparazione di glicoli eteri |
| DE2605991A1 (de) * | 1976-02-14 | 1977-08-25 | Hoechst Ag | Verfahren zur erhoehung der selektivitaet bei der herstellung von aethylenoxid |
| US4400559A (en) * | 1982-06-14 | 1983-08-23 | The Halcon Sd Group, Inc. | Process for preparing ethylene glycol |
| IL84232A (en) * | 1986-10-31 | 1992-06-21 | Shell Int Research | Catalyst and process for the catalytic production of ethylene oxide |
| DE68925767T2 (de) | 1988-08-30 | 1996-08-14 | Union Carbide Corp | Katalysatoren für die Herstellung von Ethylenoxid und Verfahren zur deren Herstellung |
| CA1337722C (en) * | 1989-04-18 | 1995-12-12 | Madan Mohan Bhasin | Alkylene oxide catalysts having enhanced activity and/or stability |
| US5177225A (en) | 1990-07-09 | 1993-01-05 | The Boc Group, Inc. | Process for the production of alkylene oxide |
| US5155242A (en) * | 1991-12-05 | 1992-10-13 | Shell Oil Company | Process for starting-up an ethylene oxide reactor |
| DE59303461D1 (de) * | 1992-02-20 | 1996-09-26 | Basf Ag | Verfahren zur Herstellung von Ethylenoxid |
| CA2078480A1 (en) * | 1992-04-20 | 1993-10-21 | Bennie Albert Horrell Jr. | Improved process for ethylene epoxidation |
| US5262551A (en) | 1992-04-20 | 1993-11-16 | Texaco Chemical Company | Process for ethylene expoxidation |
| US5447897A (en) * | 1993-05-17 | 1995-09-05 | Shell Oil Company | Ethylene oxide catalyst and process |
| WO1995005896A1 (en) * | 1993-08-23 | 1995-03-02 | Shell Internationale Research Maatschappij B.V. | Ethylene oxide catalyst |
| US5380697A (en) * | 1993-09-08 | 1995-01-10 | Shell Oil Company | Ethylene oxide catalyst and process |
| JP3403476B2 (ja) * | 1993-12-28 | 2003-05-06 | 株式会社日本触媒 | エチレンオキシドの製造方法 |
| US5545603A (en) | 1994-11-01 | 1996-08-13 | Shell Oil Company | Ethylene oxide catalyst and process |
| DE19843697A1 (de) * | 1998-09-23 | 2000-03-30 | Basf Ag | Verfahren zur Herstellung von hochreinem Monoethylenglykol |
| US6372925B1 (en) * | 2000-06-09 | 2002-04-16 | Shell Oil Company | Process for operating the epoxidation of ethylene |
-
2000
- 2000-12-12 US US09/735,360 patent/US6372925B1/en not_active Expired - Lifetime
-
2001
- 2001-06-05 JP JP2002510467A patent/JP5097325B2/ja not_active Expired - Lifetime
- 2001-06-05 CA CA2411070A patent/CA2411070C/en not_active Expired - Lifetime
- 2001-06-05 ES ES01944278T patent/ES2269421T3/es not_active Expired - Lifetime
- 2001-06-05 CN CN01811606XA patent/CN1217941C/zh not_active Expired - Lifetime
- 2001-06-05 WO PCT/US2001/018097 patent/WO2001096324A2/en not_active Ceased
- 2001-06-05 EP EP01944278A patent/EP1292587B1/en not_active Revoked
- 2001-06-05 AT AT01944278T patent/ATE342259T1/de not_active IP Right Cessation
- 2001-06-05 KR KR1020027016739A patent/KR100827473B1/ko not_active Expired - Lifetime
- 2001-06-05 RU RU2002135677/04A patent/RU2263670C2/ru not_active IP Right Cessation
- 2001-06-05 BR BRPI0111475-1A patent/BR0111475B1/pt not_active IP Right Cessation
- 2001-06-05 MX MXPA02012036A patent/MXPA02012036A/es active IP Right Grant
- 2001-06-05 US US10/297,522 patent/US6717001B2/en not_active Expired - Lifetime
- 2001-06-05 AU AU2001266704A patent/AU2001266704A1/en not_active Abandoned
- 2001-06-05 DE DE60123788T patent/DE60123788T2/de not_active Expired - Lifetime
- 2001-06-06 GC GCP20011416 patent/GC0000430A/xx active
- 2001-06-07 MY MYPI20012666A patent/MY128386A/en unknown
- 2001-06-08 TW TW090113981A patent/TWI230707B/zh not_active IP Right Cessation
-
2002
- 2002-11-27 IN IN1165DE2002 patent/IN2002DE01165A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6372925B1 (en) | 2002-04-16 |
| EP1292587B1 (en) | 2006-10-11 |
| WO2001096324A2 (en) | 2001-12-20 |
| MXPA02012036A (es) | 2003-06-06 |
| CN1437590A (zh) | 2003-08-20 |
| IN2002DE01165A (OSRAM) | 2008-09-26 |
| WO2001096324A3 (en) | 2002-03-28 |
| RU2263670C2 (ru) | 2005-11-10 |
| MX231687B (OSRAM) | 2005-10-28 |
| US20030139633A1 (en) | 2003-07-24 |
| JP2004503548A (ja) | 2004-02-05 |
| CA2411070A1 (en) | 2001-12-20 |
| KR20030034090A (ko) | 2003-05-01 |
| AU2001266704A1 (en) | 2001-12-24 |
| DE60123788D1 (de) | 2006-11-23 |
| TWI230707B (en) | 2005-04-11 |
| US6717001B2 (en) | 2004-04-06 |
| ATE342259T1 (de) | 2006-11-15 |
| EP1292587A2 (en) | 2003-03-19 |
| CN1217941C (zh) | 2005-09-07 |
| KR100827473B1 (ko) | 2008-05-06 |
| GC0000430A (en) | 2007-09-30 |
| MY128386A (en) | 2007-01-31 |
| DE60123788T2 (de) | 2007-09-06 |
| BR0111475B1 (pt) | 2012-04-17 |
| BR0111475A (pt) | 2003-03-25 |
| JP5097325B2 (ja) | 2012-12-12 |
| ES2269421T3 (es) | 2007-04-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2411070C (en) | Process for operating the epoxidation of ethylene with supported silver catalysts | |
| CA2525520C (en) | Process for the production of an olefin oxide using oxygen and a silver-containing catalyst | |
| EP1613428B1 (en) | An olefin epoxidation process and a catalyst for use in the process | |
| EP1517751B2 (en) | A method for improving the selectivity of a catalyst and a process for the epoxidation of an olefin | |
| US7657332B2 (en) | Process and systems for the epoxidation of an olefin | |
| CA2467574C (en) | A process and systems for the epoxidation of an ethylene with oxygen comprising a two phase temperature profile | |
| CN102421766B (zh) | 提高铼助催化的环氧化催化剂的效率的方法以及使用它们的环氧化方法 | |
| KR101098051B1 (ko) | 에폭시화 방법의 개시방법, 올레핀 에폭시화 촉매 및 방법 | |
| JP5507444B2 (ja) | 酸化オレフィン、１，２−ジオール、１，２−ジオールエーテル、１，２−カーボネートまたはアルカノールアミンの製造方法 | |
| CA2517360C (en) | Production of ethylene oxide from ethylene and oxygen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20210607 |