DE2117255C3 - Verfahren zur katalytischen Disproportionierung von Olefinen - Google Patents
Verfahren zur katalytischen Disproportionierung von OlefinenInfo
- Publication number
- DE2117255C3 DE2117255C3 DE2117255A DE2117255A DE2117255C3 DE 2117255 C3 DE2117255 C3 DE 2117255C3 DE 2117255 A DE2117255 A DE 2117255A DE 2117255 A DE2117255 A DE 2117255A DE 2117255 C3 DE2117255 C3 DE 2117255C3
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- olefins
- disproportionation
- carried out
- hours
- 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
- 238000000034 method Methods 0.000 title claims description 27
- 150000001336 alkenes Chemical class 0.000 title claims description 22
- 238000007323 disproportionation reaction Methods 0.000 title claims description 17
- 230000003197 catalytic effect Effects 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 50
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 29
- 239000000377 silicon dioxide Substances 0.000 claims description 12
- 229910052797 bismuth Inorganic materials 0.000 claims description 8
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 claims description 4
- VVRQVWSVLMGPRN-UHFFFAOYSA-N oxotungsten Chemical class [W]=O VVRQVWSVLMGPRN-UHFFFAOYSA-N 0.000 claims description 2
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 19
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 12
- 235000012239 silicon dioxide Nutrition 0.000 description 8
- 238000001994 activation Methods 0.000 description 7
- 230000004913 activation Effects 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 230000008929 regeneration Effects 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000002574 poison Substances 0.000 description 3
- 231100000614 poison Toxicity 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- -1 2-pemen Chemical compound 0.000 description 2
- 229910015902 Bi 2 O 3 Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- 239000010937 tungsten Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IICQZTQZQSBHBY-HWKANZROSA-N (e)-non-2-ene Chemical compound CCCCCC\C=C\C IICQZTQZQSBHBY-HWKANZROSA-N 0.000 description 1
- OTTZHAVKAVGASB-HYXAFXHYSA-N 2-Heptene Chemical compound CCCC\C=C/C OTTZHAVKAVGASB-HYXAFXHYSA-N 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N 2-heptene Natural products CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- IICQZTQZQSBHBY-UHFFFAOYSA-N 2t-nonene Natural products CCCCCCC=CC IICQZTQZQSBHBY-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 229910018871 CoO 2 Inorganic materials 0.000 description 1
- HHUIAYDQMNHELC-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O HHUIAYDQMNHELC-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910000416 bismuth oxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- TYIXMATWDRGMPF-UHFFFAOYSA-N dibismuth;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Bi+3].[Bi+3] TYIXMATWDRGMPF-UHFFFAOYSA-N 0.000 description 1
- 229940069096 dodecene Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- WZHKDGJSXCTSCK-UHFFFAOYSA-N hept-3-ene Chemical compound CCCC=CCC WZHKDGJSXCTSCK-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- YPPFWRWCZNXINO-UHFFFAOYSA-N methyl 1-hydroxy-6-phenyl-4-(trifluoromethyl)indole-2-carboxylate Chemical compound C1=C2N(O)C(C(=O)OC)=CC2=C(C(F)(F)F)C=C1C1=CC=CC=C1 YPPFWRWCZNXINO-UHFFFAOYSA-N 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical class [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
- B01J23/31—Chromium, molybdenum or tungsten combined with bismuth
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- C07C2521/08—Silica
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/12—Silica and alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2523/24—Chromium, molybdenum or tungsten
- C07C2523/31—Chromium, molybdenum or tungsten combined with bismuth
Landscapes
- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2326970 | 1970-04-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2117255A1 DE2117255A1 (de) | 1971-11-04 |
| DE2117255B2 DE2117255B2 (de) | 1973-12-13 |
| DE2117255C3 true DE2117255C3 (de) | 1974-07-18 |
Family
ID=11205483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2117255A Expired DE2117255C3 (de) | 1970-04-14 | 1971-04-08 | Verfahren zur katalytischen Disproportionierung von Olefinen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3764635A (show.php) |
| JP (1) | JPS5218164B1 (show.php) |
| BE (1) | BE765623A (show.php) |
| DE (1) | DE2117255C3 (show.php) |
| FR (1) | FR2089461A5 (show.php) |
| GB (1) | GB1306797A (show.php) |
| LU (1) | LU62979A1 (show.php) |
| NL (1) | NL155526B (show.php) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4022846A (en) * | 1971-06-25 | 1977-05-10 | Bp Chemicals International Limited | Process for producing olefins by disproportionation |
| US4490477A (en) * | 1982-07-29 | 1984-12-25 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4474897A (en) * | 1982-07-29 | 1984-10-02 | Monsanto Company | Catalyst useable in a reverse disproportionation process |
| US4419526A (en) * | 1982-07-29 | 1983-12-06 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4487849A (en) * | 1982-07-29 | 1984-12-11 | Monsanto Company | Catalyst for the reverse disproportionation process |
| US4511672A (en) * | 1982-07-29 | 1985-04-16 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4440967A (en) * | 1982-07-29 | 1984-04-03 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4439628A (en) * | 1982-07-29 | 1984-03-27 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4439626A (en) * | 1982-07-29 | 1984-03-27 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4439627A (en) * | 1982-07-29 | 1984-03-27 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4440968A (en) * | 1982-07-29 | 1984-04-03 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4448894A (en) * | 1982-07-29 | 1984-05-15 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4514519A (en) * | 1982-07-29 | 1985-04-30 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4419527A (en) * | 1982-07-29 | 1983-12-06 | Monsanto Company | Catalyst and reverse disproportionation process |
| US4539308A (en) * | 1983-10-05 | 1985-09-03 | Phillips Petroleum Company | Olefin metathesis catalyst |
| US4499328A (en) * | 1983-10-05 | 1985-02-12 | Phillips Petroleum Company | Olefin metathesis and catalyst |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2991322A (en) * | 1959-12-29 | 1961-07-04 | Shell Oil Co | Dehydrogenation in the presence of oxygen and bismuth tungstate |
| US3370103A (en) * | 1962-11-28 | 1968-02-20 | Standard Oil Co | Process for preparing diolefins |
| US3511890A (en) * | 1966-03-03 | 1970-05-12 | Phillips Petroleum Co | Olefin conversion and catalyst therefor |
| NL136583C (show.php) * | 1967-04-03 | |||
| NL135282C (show.php) * | 1967-04-03 | |||
| US3488402A (en) * | 1967-05-18 | 1970-01-06 | Sinclair Research Inc | Dehydrogenation of hydrocarbons using dehydrogenation-oxidation catalyst system |
-
1971
- 1971-04-08 DE DE2117255A patent/DE2117255C3/de not_active Expired
- 1971-04-09 FR FR7112679A patent/FR2089461A5/fr not_active Expired
- 1971-04-13 LU LU62979D patent/LU62979A1/xx unknown
- 1971-04-13 BE BE765623A patent/BE765623A/xx not_active IP Right Cessation
- 1971-04-14 NL NL7104953.A patent/NL155526B/xx not_active IP Right Cessation
- 1971-04-14 US US00134094A patent/US3764635A/en not_active Expired - Lifetime
- 1971-04-14 JP JP46023208A patent/JPS5218164B1/ja active Pending
- 1971-04-19 GB GB2669771*A patent/GB1306797A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL155526B (nl) | 1978-01-16 |
| BE765623A (fr) | 1971-08-30 |
| GB1306797A (en) | 1973-02-14 |
| NL7104953A (show.php) | 1971-10-18 |
| DE2117255B2 (de) | 1973-12-13 |
| DE2117255A1 (de) | 1971-11-04 |
| JPS5218164B1 (show.php) | 1977-05-20 |
| FR2089461A5 (show.php) | 1972-01-07 |
| LU62979A1 (show.php) | 1971-08-26 |
| US3764635A (en) | 1973-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |