CA1215963A - Isomerisation d'alcenes a l'aide d'un catalyseur a base de a1.sub.20.sub.3 - Google Patents
Isomerisation d'alcenes a l'aide d'un catalyseur a base de a1.sub.20.sub.3Info
- Publication number
- CA1215963A CA1215963A CA000437322A CA437322A CA1215963A CA 1215963 A CA1215963 A CA 1215963A CA 000437322 A CA000437322 A CA 000437322A CA 437322 A CA437322 A CA 437322A CA 1215963 A CA1215963 A CA 1215963A
- Authority
- CA
- Canada
- Prior art keywords
- butene
- mole
- range
- process according
- stream
- 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
- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims description 44
- 150000001336 alkenes Chemical class 0.000 claims abstract description 50
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 239000011734 sodium Substances 0.000 claims abstract description 21
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 20
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 20
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 44
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 15
- 239000012808 vapor phase Substances 0.000 claims description 12
- 150000001993 dienes Chemical class 0.000 claims description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 15
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims 15
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000008929 regeneration Effects 0.000 description 8
- 238000011069 regeneration method Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004939 coking Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- 229910000619 316 stainless steel Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910003828 SiH3 Inorganic materials 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- -1 n-butene Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/2705—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with metal oxides
-
- 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
- B01J21/12—Silica and alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/2213—Catalytic processes not covered by C07C5/23 - C07C5/31 with metal oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2772—Catalytic processes with metal oxides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44086282A | 1982-11-12 | 1982-11-12 | |
| US440,862 | 1982-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215963A true CA1215963A (fr) | 1986-12-30 |
Family
ID=23750484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000437322A Expired CA1215963A (fr) | 1982-11-12 | 1983-09-22 | Isomerisation d'alcenes a l'aide d'un catalyseur a base de a1.sub.20.sub.3 |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS59102437A (fr) |
| CA (1) | CA1215963A (fr) |
| DE (1) | DE3340958A1 (fr) |
| FR (1) | FR2536066B1 (fr) |
| GB (1) | GB2129701B (fr) |
| IT (1) | IT1170559B (fr) |
| NL (1) | NL191582C (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4677095A (en) * | 1985-01-31 | 1987-06-30 | Engelhard Corporation | Stabilized alumina catalyst support coatings |
| AT400951B (de) * | 1991-11-05 | 1996-05-28 | Oemv Ag | Verfahren zur katalytischen umwandlung von vier bis fünf kohlenstoffatomen aufweisenden verbindungen sowie verfahren zur herstellung eines katalysators zur durchführung des verfahrens |
| US6407302B1 (en) * | 1999-11-04 | 2002-06-18 | Bp Corporation North America Inc. | Isomerization process of a mixture containing vinyl and vinylidene olefins |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB670992A (en) * | 1949-05-30 | 1952-04-30 | Morag Lauchlan Allan | Improvements in and relating to the isomerisation of unsaturated hydrocarbons |
| GB1023647A (en) * | 1962-10-02 | 1966-03-23 | Air Prod & Chem | Catalyst preparation |
| US3558733A (en) * | 1969-07-30 | 1971-01-26 | Phillips Petroleum Co | Olefin isomerization process with alumina of controlled water content |
| IT1001614B (it) * | 1973-10-31 | 1976-04-30 | Snam Progetti | Procedimento per preparare materia li aventi proprieta meccaniche e termiche migliorate e materiali ottenuti |
| IT1017878B (it) * | 1974-08-02 | 1977-08-10 | Snam Progetti | Processo per la isomerizzazione di alcheni |
| AR204423A1 (es) * | 1974-09-19 | 1976-02-06 | Snam Progetti | Procedimiento para preparar alumina con propiedades mecanicas mejoradas y alumina asi obtenida |
| IT1025882B (it) * | 1974-11-21 | 1978-08-30 | Snam Progetti | Processo per la preparazione dieteri |
| US4225419A (en) * | 1979-04-18 | 1980-09-30 | Phillips Petroleum Company | Alumina isomerization process |
| FR2484400A1 (fr) * | 1980-05-13 | 1981-12-18 | Inst Francais Du Petrole | Procede d'isomerisation d'olefines |
-
1983
- 1983-09-22 CA CA000437322A patent/CA1215963A/fr not_active Expired
- 1983-09-30 GB GB08326271A patent/GB2129701B/en not_active Expired
- 1983-11-02 IT IT49261/83A patent/IT1170559B/it active
- 1983-11-07 NL NL8303824A patent/NL191582C/xx not_active IP Right Cessation
- 1983-11-08 FR FR8317751A patent/FR2536066B1/fr not_active Expired
- 1983-11-11 DE DE19833340958 patent/DE3340958A1/de active Granted
- 1983-11-11 JP JP58212287A patent/JPS59102437A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT8349261A0 (it) | 1983-11-02 |
| IT1170559B (it) | 1987-06-03 |
| GB2129701A (en) | 1984-05-23 |
| DE3340958C2 (fr) | 1992-11-19 |
| NL191582B (nl) | 1995-06-01 |
| NL191582C (nl) | 1995-10-03 |
| NL8303824A (nl) | 1984-06-01 |
| FR2536066B1 (fr) | 1986-10-24 |
| JPS59102437A (ja) | 1984-06-13 |
| FR2536066A1 (fr) | 1984-05-18 |
| GB8326271D0 (en) | 1983-11-02 |
| GB2129701B (en) | 1986-10-08 |
| DE3340958A1 (de) | 1984-05-17 |
| JPH0472809B2 (fr) | 1992-11-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0511013B1 (fr) | Fabrication d'oléfines | |
| EP0192059B1 (fr) | Procédé pour la déshydro-isomérisation d'hydrocarbures | |
| US3686334A (en) | Direct hydration of ethylene to ethanol | |
| EP0109059A1 (fr) | Procédé pour convertir des oléfines ayant de 4 à 12 atomes de carbone en propène | |
| US8049054B2 (en) | Process for the preparation of C5 and/or C6 olefin | |
| US5628880A (en) | Etherification--hydrogenation process | |
| EP0064046A1 (fr) | Alkylation de composés aromatiques avec des catalyseurs de type silicalite, en présence de vapeur d'eau | |
| EP0090569B1 (fr) | Procédé pour l'oligomérisation d'isobutène | |
| US4038337A (en) | Process for isomerizing alkenes | |
| EP0091662B1 (fr) | Catalyseurs et procédé pour la déshydratation de 2-alcohols | |
| CA1215963A (fr) | Isomerisation d'alcenes a l'aide d'un catalyseur a base de a1.sub.20.sub.3 | |
| GB2121431A (en) | Isomerisation of butene-1 to butene-2 in isobutylene | |
| AU2007253402B2 (en) | Process for the preparation of propylene from a hydrocarbon feed | |
| US5043523A (en) | Al2 O3 alkene isomerization process and catalyst | |
| US11174207B2 (en) | Process for the isomerization of olefins | |
| US2395274A (en) | Isomerization process | |
| US4774376A (en) | Production of liquid products from aliphatic hydrocarbons | |
| FI81778B (fi) | Reglering av vaermebalansen i katalytisk dehydrogenering av isobutan. | |
| RU2027693C1 (ru) | Способ окислительного дегидрирования изоамиленов | |
| US4291181A (en) | Indenes from tetrahydroindenes | |
| US4436949A (en) | Olefin conversion process | |
| US4367362A (en) | Process for the isomerization of N-alkenes | |
| CA1274549A (fr) | Traitement catalytique | |
| CA2451122C (fr) | Procede d'isomerisation d'une olefine vinylidene | |
| EP0758635B1 (fr) | Procédé pour l'isomérisation des oléfines |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |