CA2822796C - Procede de metathese d'olefines et catalyseur contenant des liaisons tungstene-fluor - Google Patents
Procede de metathese d'olefines et catalyseur contenant des liaisons tungstene-fluor Download PDFInfo
- Publication number
- CA2822796C CA2822796C CA2822796A CA2822796A CA2822796C CA 2822796 C CA2822796 C CA 2822796C CA 2822796 A CA2822796 A CA 2822796A CA 2822796 A CA2822796 A CA 2822796A CA 2822796 C CA2822796 C CA 2822796C
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- olefin
- support
- tungsten
- compound
- 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
- 238000000034 method Methods 0.000 title claims abstract description 104
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- 239000003054 catalyst Substances 0.000 title claims abstract description 85
- 238000005865 alkene metathesis reaction Methods 0.000 title claims description 51
- 150000001336 alkenes Chemical class 0.000 claims abstract description 94
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 72
- -1 tungsten metal compound Chemical class 0.000 claims abstract description 42
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 40
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 39
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000005977 Ethylene Substances 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000010937 tungsten Substances 0.000 claims abstract description 33
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 31
- 238000005649 metathesis reaction Methods 0.000 claims abstract description 28
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 53
- 229930195733 hydrocarbon Natural products 0.000 claims description 49
- 150000002430 hydrocarbons Chemical class 0.000 claims description 49
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 11
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 9
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 229910052751 metal Inorganic materials 0.000 claims description 5
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 9
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
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- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
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- 229910052731 fluorine Inorganic materials 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- 230000003197 catalytic effect Effects 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
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- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012025 fluorinating agent Substances 0.000 description 2
- 239000003502 gasoline Substances 0.000 description 2
- 239000003349 gelling agent Substances 0.000 description 2
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- 229910052809 inorganic oxide Inorganic materials 0.000 description 2
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- 150000002513 isocyanates Chemical class 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- 238000000197 pyrolysis Methods 0.000 description 1
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- 238000004064 recycling Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/122—Metal aryl or alkyl compounds
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
- B01J37/03—Precipitation; Co-precipitation
- B01J37/031—Precipitation
- B01J37/035—Precipitation on carriers
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/60—Complexes comprising metals of Group VI (VIA or VIB) as the central metal
- B01J2531/66—Tungsten
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- 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
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock
-
- 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
- Y02P30/00—Technologies relating to oil refining and petrochemical industry
- Y02P30/40—Ethylene production
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201061427884P | 2010-12-29 | 2010-12-29 | |
US201061427893P | 2010-12-29 | 2010-12-29 | |
US61/427,893 | 2010-12-29 | ||
US61/427,884 | 2010-12-29 | ||
US13/156,860 US8935891B2 (en) | 2011-06-09 | 2011-06-09 | Olefin metathesis catalyst containing tungsten fluorine bonds |
US13/156,918 US20120316374A1 (en) | 2011-06-09 | 2011-06-09 | Olefin metathesis process using a catalyst containing tungsten fluorine bonds |
US13/156,860 | 2011-06-09 | ||
US13/156,918 | 2011-06-09 | ||
PCT/US2011/066065 WO2012092014A2 (fr) | 2010-12-29 | 2011-12-20 | Procédé de métathèse d'oléfines et catalyseur contenant des liaisons tungstène-fluor |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2822796A1 CA2822796A1 (fr) | 2012-07-05 |
CA2822796C true CA2822796C (fr) | 2016-05-31 |
Family
ID=46383808
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2822796A Expired - Fee Related CA2822796C (fr) | 2010-12-29 | 2011-12-20 | Procede de metathese d'olefines et catalyseur contenant des liaisons tungstene-fluor |
Country Status (8)
Country | Link |
---|---|
EP (1) | EP2658648A4 (fr) |
JP (1) | JP5662587B2 (fr) |
CN (1) | CN103269791B (fr) |
CA (1) | CA2822796C (fr) |
MX (1) | MX2013007351A (fr) |
SG (1) | SG191375A1 (fr) |
TW (1) | TWI458551B (fr) |
WO (1) | WO2012092014A2 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201506684D0 (en) * | 2015-04-20 | 2015-06-03 | Isis Innovation | Tungsten catalysts |
JP7051873B2 (ja) | 2017-01-05 | 2022-04-11 | サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ | 廃棄プラスチックのプロピレンおよびクメンへの変換 |
WO2018127813A1 (fr) * | 2017-01-05 | 2018-07-12 | Sabic Global Technologies, B.V. | Conversion de déchets plastiques en propylène et cumène |
KR102296488B1 (ko) | 2020-04-06 | 2021-09-01 | 한국생산기술연구원 | 로봇 그리퍼 모듈 |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3923920A (en) * | 1971-03-29 | 1975-12-02 | Phillips Petroleum Co | Olefin disproportionation catalyst and process for using same |
EP0084437A1 (fr) * | 1982-01-13 | 1983-07-27 | BP Chemicals Limited | Dismutation d'oléfines fonctionalisées |
EP0129474B1 (fr) * | 1983-06-15 | 1986-04-23 | Societe Nationale Elf Aquitaine | Catalyseur perfectionné pour la métathèse d'oléfines |
FR2547513B1 (fr) * | 1983-06-15 | 1986-03-21 | Elf Aquitaine | Catalyseur perfectionne pour la metathese d'olefines |
FR2577216B1 (fr) * | 1985-02-12 | 1987-09-11 | Elf Aquitaine | Perfectionnement a la metathese d'olefines avec un catalyseur a base d'un complexe de tungstene |
FI86298C (fi) * | 1990-12-05 | 1992-08-10 | Neste Oy | Metatesprocess foer olefiner och katalysator foer tillaempning av denna. |
US5639900A (en) * | 1993-12-29 | 1997-06-17 | Metton America, Inc. | Thermally activated olefin metathesis catalyst precursor |
BE1008339A3 (nl) * | 1994-05-03 | 1996-04-02 | Dsm Nv | Heterogene metathesekatalysator. |
US5914433A (en) | 1997-07-22 | 1999-06-22 | Uop Lll | Process for producing polymer grade olefins |
US20050124839A1 (en) * | 2001-06-13 | 2005-06-09 | Gartside Robert J. | Catalyst and process for the metathesis of ethylene and butene to produce propylene |
US6867341B1 (en) | 2002-09-17 | 2005-03-15 | Uop Llc | Catalytic naphtha cracking catalyst and process |
US7074976B2 (en) * | 2003-08-19 | 2006-07-11 | Equistar Chemicals, Lp | Propylene production |
US7268265B1 (en) | 2004-06-30 | 2007-09-11 | Uop Llc | Apparatus and process for light olefin recovery |
CN101304963A (zh) * | 2005-11-14 | 2008-11-12 | 三井化学株式会社 | 含有来源于生物有机体的碳的丙烯的制造方法 |
US7459593B1 (en) * | 2005-11-18 | 2008-12-02 | Uop Llc | Metathesis unit pretreatment process with formation of octene |
EP3281931A1 (fr) * | 2006-10-13 | 2018-02-14 | Elevance Renewable Sciences, Inc. | Procédés de production de composés organiques par métathèse |
US7586018B2 (en) | 2006-12-21 | 2009-09-08 | Uop Llc | Oxygenate conversion to olefins with dimerization and metathesis |
-
2011
- 2011-12-20 MX MX2013007351A patent/MX2013007351A/es not_active Application Discontinuation
- 2011-12-20 JP JP2013547539A patent/JP5662587B2/ja active Active
- 2011-12-20 CN CN201180061787.7A patent/CN103269791B/zh not_active Expired - Fee Related
- 2011-12-20 SG SG2013049598A patent/SG191375A1/en unknown
- 2011-12-20 WO PCT/US2011/066065 patent/WO2012092014A2/fr active Application Filing
- 2011-12-20 EP EP11853350.4A patent/EP2658648A4/fr not_active Withdrawn
- 2011-12-20 CA CA2822796A patent/CA2822796C/fr not_active Expired - Fee Related
- 2011-12-26 TW TW100148707A patent/TWI458551B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
TWI458551B (zh) | 2014-11-01 |
JP2014511256A (ja) | 2014-05-15 |
EP2658648A2 (fr) | 2013-11-06 |
TW201233441A (en) | 2012-08-16 |
WO2012092014A3 (fr) | 2013-01-17 |
CA2822796A1 (fr) | 2012-07-05 |
MX2013007351A (es) | 2013-08-01 |
SG191375A1 (en) | 2013-08-30 |
CN103269791B (zh) | 2015-09-30 |
JP5662587B2 (ja) | 2015-02-04 |
EP2658648A4 (fr) | 2015-03-25 |
WO2012092014A2 (fr) | 2012-07-05 |
CN103269791A (zh) | 2013-08-28 |
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