DE69400234T2 - Kontinuierliches Verfahren zur Isomerisierung von Olefinen mit Katalysatorregenerierung - Google Patents
Kontinuierliches Verfahren zur Isomerisierung von Olefinen mit KatalysatorregenerierungInfo
- Publication number
- DE69400234T2 DE69400234T2 DE69400234T DE69400234T DE69400234T2 DE 69400234 T2 DE69400234 T2 DE 69400234T2 DE 69400234 T DE69400234 T DE 69400234T DE 69400234 T DE69400234 T DE 69400234T DE 69400234 T2 DE69400234 T2 DE 69400234T2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- line
- steam
- reaction zone
- reactor
- 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
- 239000003054 catalyst Substances 0.000 title claims description 121
- 238000011069 regeneration method Methods 0.000 title claims description 29
- 230000008929 regeneration Effects 0.000 title claims description 27
- 238000006317 isomerization reaction Methods 0.000 title claims description 17
- 238000010924 continuous production Methods 0.000 title claims description 7
- 150000001336 alkenes Chemical class 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 25
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 18
- 239000007789 gas Substances 0.000 claims description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052719 titanium Inorganic materials 0.000 claims description 11
- 239000010936 titanium Substances 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 10
- 238000002485 combustion reaction Methods 0.000 description 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 239000000571 coke Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical class CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 4
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical class CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- WIXLCZYMZOINPV-UHFFFAOYSA-J oxalate titanium(4+) decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Ti+4].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O WIXLCZYMZOINPV-UHFFFAOYSA-J 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 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
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/06—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst using steam
-
- 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
- B01J21/20—Regeneration or reactivation
-
- 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
-
- 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
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9301389A FR2701258B1 (fr) | 1993-02-09 | 1993-02-09 | Procédé continu pour l'isomérisation des oléfines. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69400234D1 DE69400234D1 (de) | 1996-07-18 |
| DE69400234T2 true DE69400234T2 (de) | 1996-10-10 |
Family
ID=9443858
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69400234T Expired - Fee Related DE69400234T2 (de) | 1993-02-09 | 1994-01-31 | Kontinuierliches Verfahren zur Isomerisierung von Olefinen mit Katalysatorregenerierung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5686648A (OSRAM) |
| EP (1) | EP0611185B1 (OSRAM) |
| JP (1) | JPH06256230A (OSRAM) |
| KR (1) | KR100300493B1 (OSRAM) |
| CN (1) | CN1045951C (OSRAM) |
| CA (1) | CA2115341A1 (OSRAM) |
| DE (1) | DE69400234T2 (OSRAM) |
| ES (1) | ES2091098T3 (OSRAM) |
| FR (1) | FR2701258B1 (OSRAM) |
| MY (1) | MY110135A (OSRAM) |
| NO (1) | NO307701B1 (OSRAM) |
| TW (1) | TW279159B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8722557B2 (en) | 2008-12-30 | 2014-05-13 | Lyondell Chemical Technology, L.P. | Catalyst regeneration |
| WO2015077332A1 (en) * | 2013-11-20 | 2015-05-28 | Lummus Technology Inc. | Olefin double bond isomerization catalyst with high poison resistance |
| DE102013226370A1 (de) * | 2013-12-18 | 2015-06-18 | Evonik Industries Ag | Herstellung von Butadien durch oxidative Dehydrierung von n-Buten nach vorhergehender Isomerisierung |
| US9314785B1 (en) | 2014-11-13 | 2016-04-19 | Chevron U.S.A. Inc. | Ketonization process using oxidative catalyst regeneration |
| CN109851464B (zh) * | 2017-11-30 | 2021-11-19 | 中国石油化工股份有限公司 | 一种正丁烯异构化的方法及装置 |
| CN109851465B (zh) * | 2017-11-30 | 2021-11-19 | 中国石油化工股份有限公司 | 一种正丁烯异构化的方法及装置 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1252364B (de) * | 1966-02-23 | 1967-10-19 | Farbenfabriken Bayer Aktienge Seilschaft, I everkusen | Verfah ren zur Gewinnung des Kallikrem Inakti vators in kristallisierter Form |
| US3558733A (en) * | 1969-07-30 | 1971-01-26 | Phillips Petroleum Co | Olefin isomerization process with alumina of controlled water content |
| US4225419A (en) * | 1979-04-18 | 1980-09-30 | Phillips Petroleum Company | Alumina isomerization process |
| EP0032543A1 (de) * | 1980-01-10 | 1981-07-29 | Chemische Werke Hüls Ag | Verfahren zur Isomerisierung von n-Alkenen |
| FR2484400A1 (fr) * | 1980-05-13 | 1981-12-18 | Inst Francais Du Petrole | Procede d'isomerisation d'olefines |
| US5182247A (en) * | 1991-02-11 | 1993-01-26 | Texaco Inc. | Sulfated catalyst for skeletal isomerization of olefins |
| FR2695636B1 (fr) * | 1992-09-15 | 1994-12-02 | Inst Francais Du Petrole | Procédé pour l'isomérisation des oléfines. |
-
1993
- 1993-02-09 FR FR9301389A patent/FR2701258B1/fr not_active Expired - Fee Related
-
1994
- 1994-01-31 EP EP94400203A patent/EP0611185B1/fr not_active Expired - Lifetime
- 1994-01-31 ES ES94400203T patent/ES2091098T3/es not_active Expired - Lifetime
- 1994-01-31 DE DE69400234T patent/DE69400234T2/de not_active Expired - Fee Related
- 1994-02-07 NO NO940391A patent/NO307701B1/no not_active IP Right Cessation
- 1994-02-08 MY MYPI94000286A patent/MY110135A/en unknown
- 1994-02-08 KR KR1019940002380A patent/KR100300493B1/ko not_active Expired - Fee Related
- 1994-02-09 CN CN94101566A patent/CN1045951C/zh not_active Expired - Lifetime
- 1994-02-09 CA CA002115341A patent/CA2115341A1/fr not_active Abandoned
- 1994-02-09 JP JP6015571A patent/JPH06256230A/ja active Pending
- 1994-02-17 TW TW083101270A patent/TW279159B/zh active
-
1995
- 1995-06-06 US US08/487,091 patent/US5686648A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CN1045951C (zh) | 1999-10-27 |
| NO940391L (no) | 1994-08-10 |
| CN1098083A (zh) | 1995-02-01 |
| ES2091098T3 (es) | 1996-10-16 |
| KR100300493B1 (ko) | 2001-10-22 |
| KR940019656A (ko) | 1994-09-14 |
| JPH06256230A (ja) | 1994-09-13 |
| EP0611185B1 (fr) | 1996-06-12 |
| NO940391D0 (no) | 1994-02-07 |
| NO307701B1 (no) | 2000-05-15 |
| MY110135A (en) | 1998-02-28 |
| US5686648A (en) | 1997-11-11 |
| CA2115341A1 (fr) | 1994-08-10 |
| FR2701258B1 (fr) | 1995-04-28 |
| TW279159B (OSRAM) | 1996-06-21 |
| FR2701258A1 (fr) | 1994-08-12 |
| DE69400234D1 (de) | 1996-07-18 |
| EP0611185A1 (fr) | 1994-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |