WO2001062689A1 - Conversion of oxygenate to olefins with staged injection of oxygenate - Google Patents
Conversion of oxygenate to olefins with staged injection of oxygenate Download PDFInfo
- Publication number
- WO2001062689A1 WO2001062689A1 PCT/US2001/004503 US0104503W WO0162689A1 WO 2001062689 A1 WO2001062689 A1 WO 2001062689A1 US 0104503 W US0104503 W US 0104503W WO 0162689 A1 WO0162689 A1 WO 0162689A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oxygenate
- process according
- zsm
- fluidized bed
- reaction zone
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/50—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the eroionite or offretite type, e.g. zeolite T
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/65—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the ferrierite type, e.g. types ZSM-21, ZSM-35 or ZSM-38
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/82—Phosphates
- C07C2529/84—Aluminophosphates containing other elements, e.g. metals, boron
- C07C2529/85—Silicoaluminophosphates (SAPO compounds)
-
- 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
Definitions
- the present invention relates to a process for converting oxygenate, such as methanol and/or dimethylether, to olefins in a reactor over a molecular sieve catalyst such as ZSM-34 and SAPO-34 wherein oxygenate is introduced to a catalyst bed at multiple injection points along the flow axis of the reactor.
- the process is especially useful for increasing ethylene selectivity.
- Olefin manufacturing processes such as steam cracking, generally operate at low pressure, high temperature, and with diluents, such as steam, to enhance yields of light olefins which are thermodynamically favored by these conditions.
- the selectivity to ethylene can be increased to some extent by increasing reactor severity, e.g.
- stagewise injection of reagents has been used in various fixed bed processes.
- U.S. Patent Nos. 4,377,718 and 4,761 ,513 describe toluene alkylation processes wherein the alkylatjng reagent is fed at different stages between fixed beds.
- U.S. Patent No. 3,751 ,504 discloses a similar procedure, using multiple injection ports, for preparing ethylbenzene using a fixed bed catalyst reactor.
- U.S. Patent No. 5,120,890 discloses multiple reactant injection locations into separate fixed beds in a process for reducing benzene and toluene content in light gasoline streams.
- the processes and systems according to this invention use stagewise injection of oxygenate by introducing the oxygenate into a catalyst bed at plural stages along the flow axis of the reactor.
- the present invention relates to a process for converting oxygenate to an olefin-containing product, comprising: introducing oxygenate into a reactor system at plural stages along a flow axis of a reactor catalyst bed; contacting the oxygenate with an oxygenate to olefin conversion molecular sieve catalyst under oxygenate to olefin conversion conditions; and recovering an olefin-containing product which contains a higher proportion of ethylene than a product produced from a process which differs only by introducing oxygenate at a single stage along the flow axis of the reactor catalyst bed.
- oxygenates including particularly methanol
- oxygenate e.g., oxygenate selected from the group consisting of methanol and dimethylether
- a molecular sieve catalyst e.g., ZSM-5, ZSM- 34 or SAPO-34
- the conversion of oxygenate to olefin according to the present invention may occur in a reactor of any configuration. Continuous reactors, such as dense fluidized bed, riser, fast fluid-bed, or fixed bed, are suitable configurations for use in the present invention.
- the reactor is a fluidized bed flow reactor type.
- the catalyst may be used in various forms, such as a fixed bed, moving bed, fluidized bed, e.g., a dense fluid bed, in suspension in the generally gaseous reaction mixture.
- the reactor catalyst bed comprises a fluidized bed reaction zone which includes a top portion, a bottom portion, and an intermediate portion extending between the top portion and the bottom portion.
- Oxygenate is introduced at a first location at or near the bottom portion of the fluidized bed reaction zone, and at a second location in the intermediate portion of the fluidized bed reaction zone.
- Oxygenate can be introduced to the fluidized bed reaction zone at a plurality of different axial positions in the intermediate portion of the fluidized bed reaction zone.
- the catalyst employed in the present invention may comprise a shape-selective zeolite having a Constraint Index of 1-12. Details of the Constraint Index test procedures are provided in J. Catalysis 67, 218-222 (1981) and in U.S. Pat. No. 4,711 ,710 Chen et al. Preferred shape selective zeolites are exemplified by ZSM-5, ZSM-11 , ZSM-12, ZSM-23, ZSM-35, ZSM-38, ZSM-48, ZSM-57 and similar materials. ZSM-5 is described in U.S. Pat. No. 3,702,886, U.S. Reissue 29,948 and in U.S. Pat. No.
- Suitable catalysts for use in the present invention include molecular sieves of, pore size ranging from about 5.0 Angstroms to about 4.0 Angstroms, preferably from about 4.8 Angstroms to about 4.4 Angstroms.
- the small pore molecular sieve employed in the reaction is of pore size ranging between about 5.0 Angstroms and 4.0 Angstroms, preferably about 4.8 Angstroms and 4.4 Angstroms, and comprised of a crystalline framework oxide component.
- the pore apertures of the molecular sieve structure consist of from about 6- to about 10-, preferably 8-membered ring structures.
- Such materials include natural and synthetic crystalline structures with tetrahedral framework oxide components such as aluminum, silicon, phosphorus and the like.
- Such catalysts are preferably selected from the group consisting of zeolites, tetrahedral aluminophosphates (ALPOs) and tetrahedral silicoaluminophosphates (SAPOs).
- APOs tetrahedral aluminophosphates
- SAPOs tetrahedral silicoaluminophosphates
- Exemplary of small pore zeolitic catalysts are ZSM-34 described in U.S. Pat. No.
- U.S. Pat. No. 3,911 ,041 discloses a process for converting oxygenate to a reaction product containing light olefins by contact of the oxygenate with a phosphorus modified zeolite.
- a zeolite of intermediate pore size, such as ZSM-5 is modified by incorporating from about 0.78 wt. % to 4.5 wt. % phosphorus bonded to its structural framework.
- the dry ZSM-5 zeolite is contacted with a solution of a phosphorus-containing compound, e.g., PCI 3 , and heated at elevated temperature for a time sufficient to incorporate the phosphorus within the crystalline framework of the zeolite.
- a phosphorus-containing compound e.g., PCI 3
- Selectivated catalysts i.e., catalysts treated to preferentially produce a particular compound
- Such selectivated catalysts are known in this art.
- Selectivated small pore zeolitic catalysts of the type described above, e.g., ZSM-34 are particularly useful. Selectivation of such materials can be carried out by conventional methods such as phosphorus modification. Examples of selectivated small pore materials suitable for use in the present invention can be found in U.S. Patent No. 5,925,586 to Sun, which discloses treatment of molecular sieve with phosphonitriiic oligomers.
- the oxygenate-containing feed with or without optional diluent e.g., steam, water, hydrogen, nitrogen, and/or light hydrocarbon gas
- the oxygenate can be introduced via feed line 13 into the fluidized bed reaction zone 14 at plural locations.
- the oxygenate is introduced at plural locations in the fluidized bed reaction zone 14; preferably these locations include one at or near its bottom portion 18.
- the oxygenate reactant preferably is introduced in gaseous form and provides at least a portion of the gas flow necessary for maintaining the reaction zone 14 in fluidized form.
- This reactant can be introduced using any appropriate introduction device 24, including conventional devices known in the art (e.g., injector nozzles, perforated grids, pipe grids, etc.).
- oxygenate reagent introduction device or port can be provided at or around the top portion 16 of the fluidized bed, without departing from the invention.
- Oxygenate and optional diluent can be mixed together prior to introducing the materials into the bottom 18 of the fluidized bed reaction zone 14, such that these materials are introduced in a common feed stream.
- the materials can be introduced separately into the fluidized bed reaction zone 14 and contacted together after their introduction, or the materials can be first mixed together in a nozzle or other device that introduces both concurrently into the fluidized bed reaction zone 14. Any suitable mixing device and method can be used for this introduction without departing from the invention.
- the reactor vessel 12 and the reactant introduction rates are maintained under suitable conditions to support a catalytic oxygenate conversion to olefin-containing product reaction to produce the desired product.
- This reaction product preferably is produced in a gaseous form, and it may be collected and recovered from the reactor outlet stream 40 in any suitable manner, such as by condensation, compression, and subsequent fractio ⁇ ation of the hydrocarbon liquid using conventional distillation and recovery equipment. Further purification of the product can be accomplished in any suitable manner, for example, by selective hydrogenation.
- Unreacted feeds can be recycled to the fluidized bed reaction zone 14. It is generally not necessary to completely purify the recycled oxygenate, although this can be done, if desired. Any dimethylether product formed can also be recycled back to the reactor for conversion to olefinic products.
- an oxygenated feed e.g., methanol, suitably with added optional diluent
- a fixed, i moving, or fluidized bed, or beds, of the above catalyst at reaction conditions, typically and preferably within the ranges given below:
- the fluidized beds used in the present invention can be relatively dense, such as turbulent sub-transport fluid beds with an operating bed density of about 200 to 700 kg/m 3 , preferably about 300 to 500 kg/m 3 .
- the use of these dense beds increases the catalyst concentration at the area of oxygenate injection.
- a suitable alternate fluid bed design is termed a fast fluid bed. This is typically characterized by a bed density that is lower than that prevailing in a dense fluid bed. Superficial gas velocities are typically greater than 1.5 m/second.
- the fluidized bed in a fast fluid bed is less defined than that in a dense fluid bed.
- FIGURE is collected from the hydrocarbon liquid and can be further processed, e.g., by condensation, compression and fractionation, as described above.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Oxygen, Ozone, And Oxides In General (AREA)
Abstract
Description
Claims
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE60102800T DE60102800T2 (en) | 2000-02-22 | 2001-02-13 | IMPLEMENTATION OF OXYGEN COMPOUNDS TO OLEFINS WITH PRESENT INJECTION OF THE OXYGEN COMPOUND |
AT01914365T ATE264283T1 (en) | 2000-02-22 | 2001-02-13 | CONVERSION OF OXYGEN COMPOUNDS TO OLEFINS WITH STAGED INJECTION OF THE OXYGEN COMPOUND |
CA002398387A CA2398387A1 (en) | 2000-02-22 | 2001-02-13 | Conversion of oxygenate to olefins with staged injection of oxygenate |
EP01914365A EP1257515B1 (en) | 2000-02-22 | 2001-02-13 | Conversion of oxygenate to olefins with staged injection of oxygenate |
MXPA02008196A MXPA02008196A (en) | 2000-02-22 | 2001-02-13 | Conversion of oxygenate to olefins with staged injection of oxygenate. |
AU39759/01A AU780007B2 (en) | 2000-02-22 | 2001-02-13 | Conversion of oxygenate to olefins with staged injection of oxygenate |
NO20023910A NO20023910D0 (en) | 2000-02-22 | 2002-08-16 | Conversion of oxygenate to olefins with stepwise injection of oxygenate |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/507,838 | 2000-02-22 | ||
US09/507,838 US7232936B1 (en) | 2000-02-22 | 2000-02-22 | Conversion of oxygenate to olefins with staged injection of oxygenate |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001062689A1 true WO2001062689A1 (en) | 2001-08-30 |
Family
ID=24020340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2001/004503 WO2001062689A1 (en) | 2000-02-22 | 2001-02-13 | Conversion of oxygenate to olefins with staged injection of oxygenate |
Country Status (12)
Country | Link |
---|---|
US (1) | US7232936B1 (en) |
EP (1) | EP1257515B1 (en) |
CN (1) | CN1190395C (en) |
AT (1) | ATE264283T1 (en) |
AU (1) | AU780007B2 (en) |
CA (1) | CA2398387A1 (en) |
DE (1) | DE60102800T2 (en) |
ES (1) | ES2218398T3 (en) |
MX (1) | MXPA02008196A (en) |
NO (1) | NO20023910D0 (en) |
WO (1) | WO2001062689A1 (en) |
ZA (1) | ZA200206527B (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7084319B2 (en) | 2003-12-05 | 2006-08-01 | Exxonmobil Chemical Patents Inc. | Catalyst fluidization in oxygenate to olefin reaction systems |
US7232936B1 (en) | 2000-02-22 | 2007-06-19 | Exxonmobil Chemical Patents Inc. | Conversion of oxygenate to olefins with staged injection of oxygenate |
WO2009065848A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefinic product |
WO2009065855A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefin |
WO2009065876A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefinic product |
US7619127B2 (en) * | 2003-12-23 | 2009-11-17 | Exxonmobil Chemical Patents Inc. | Method of operating a riser reactor |
US7744746B2 (en) | 2006-03-31 | 2010-06-29 | Exxonmobil Research And Engineering Company | FCC catalyst stripper configuration |
WO2010072730A1 (en) | 2008-12-22 | 2010-07-01 | Shell Internationale Research Maatschappij B.V. | A riser reactor system and a process for the preparation of an olefinic product |
US7799118B2 (en) | 2006-03-31 | 2010-09-21 | Exxonmobil Chemical Patents Inc. | Product recovery in gas-solids reactors |
US8049054B2 (en) | 2006-05-19 | 2011-11-01 | Shell Oil Company | Process for the preparation of C5 and/or C6 olefin |
US8083815B2 (en) | 2008-12-22 | 2011-12-27 | Shell Oil Company | Process to prepare methanol and/or dimethylether |
US8168842B2 (en) | 2006-05-19 | 2012-05-01 | Shell Oil Company | Process for the alkylation of a cycloalkene |
WO2013004111A1 (en) * | 2011-07-07 | 2013-01-10 | 南京大学 | Integrated system technique for coupling fixed bed and jet fluidized bed to separator unit |
KR20190062545A (en) * | 2016-10-19 | 2019-06-05 | 달리안 인스티튜트 오브 케미컬 피직스, 차이니즈 아카데미 오브 사이언시즈 | Process for producing propylene, C4 hydrocarbons and apparatus therefor |
KR20190062546A (en) * | 2016-10-19 | 2019-06-05 | 달리안 인스티튜트 오브 케미컬 피직스, 차이니즈 아카데미 오브 사이언시즈 | Process and apparatus for producing propylene and C4 hydrocarbons |
KR20190068585A (en) * | 2016-10-19 | 2019-06-18 | 달리안 인스티튜트 오브 케미컬 피직스, 차이니즈 아카데미 오브 사이언시즈 | Turbulent fluidized bed reactor, apparatus and method for producing propylene and C4 hydrocarbons from oxygen-containing compounds |
KR20190068584A (en) * | 2016-10-19 | 2019-06-18 | 달리안 인스티튜트 오브 케미컬 피직스, 차이니즈 아카데미 오브 사이언시즈 | Fast fluidized bed reactor, apparatus and method for producing propylene and C4 hydrocarbons from oxygen-containing compounds |
Families Citing this family (12)
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US8415518B2 (en) * | 2006-08-03 | 2013-04-09 | Exxonmobil Chemical Patents Inc. | Production of light olefins |
CN101239870B (en) * | 2007-02-07 | 2011-08-17 | 中国石油化工股份有限公司 | Process for converting methanol or ethanol to preparing low-carbon olefins |
CN101157593B (en) * | 2007-03-07 | 2010-09-22 | 中国科学院大连化学物理研究所 | Method for producing light olefins by methanol or/and dimethyl ether |
CN102464557B (en) * | 2010-11-17 | 2014-03-26 | 中国石油化工股份有限公司 | Method for preparing dimethylbenzene from oxygen-containing compound and methylbenzene |
CN102875291B (en) * | 2011-07-12 | 2014-11-26 | 中国石油化工股份有限公司 | Method for producing low-carbon olefins from methanol |
TWI495511B (en) * | 2011-07-27 | 2015-08-11 | Exxonmobil Chem Patents Inc | Fluid bed reactor with staged baffles |
CN105324355B (en) * | 2013-03-29 | 2019-02-15 | 环球油品公司 | For improving the dynamic (dynamical) reactor multichannel grid of catalyst flow |
CN107434755B (en) * | 2016-05-27 | 2020-02-04 | 中国科学院大连化学物理研究所 | Preparation method of low-carbon olefin |
CN107961745B (en) * | 2016-10-19 | 2021-12-14 | 中国科学院大连化学物理研究所 | Turbulent fluidized bed reactor, device and method for preparing propylene and C4 hydrocarbons from oxygen-containing compounds |
CN108786671B (en) | 2017-04-27 | 2021-04-23 | 中国科学院大连化学物理研究所 | Fluidized bed device and method for preparing p-xylene and co-producing low-carbon olefin by methanol and/or dimethyl ether and benzene |
US10556214B2 (en) | 2017-12-20 | 2020-02-11 | Uop Llc | Apparatuses for mixing of staged methanol injection |
CN113387762A (en) * | 2020-03-13 | 2021-09-14 | 中国石油化工股份有限公司 | Process for converting methanol in a fluidized bed reactor with required temperature control |
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-
2000
- 2000-02-22 US US09/507,838 patent/US7232936B1/en not_active Expired - Lifetime
-
2001
- 2001-02-13 ES ES01914365T patent/ES2218398T3/en not_active Expired - Lifetime
- 2001-02-13 AU AU39759/01A patent/AU780007B2/en not_active Ceased
- 2001-02-13 WO PCT/US2001/004503 patent/WO2001062689A1/en active IP Right Grant
- 2001-02-13 AT AT01914365T patent/ATE264283T1/en not_active IP Right Cessation
- 2001-02-13 DE DE60102800T patent/DE60102800T2/en not_active Expired - Fee Related
- 2001-02-13 MX MXPA02008196A patent/MXPA02008196A/en not_active Application Discontinuation
- 2001-02-13 CA CA002398387A patent/CA2398387A1/en not_active Abandoned
- 2001-02-13 CN CNB018054099A patent/CN1190395C/en not_active Expired - Lifetime
- 2001-02-13 EP EP01914365A patent/EP1257515B1/en not_active Expired - Lifetime
-
2002
- 2002-08-15 ZA ZA200206527A patent/ZA200206527B/en unknown
- 2002-08-16 NO NO20023910A patent/NO20023910D0/en not_active Application Discontinuation
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Cited By (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7232936B1 (en) | 2000-02-22 | 2007-06-19 | Exxonmobil Chemical Patents Inc. | Conversion of oxygenate to olefins with staged injection of oxygenate |
US7084319B2 (en) | 2003-12-05 | 2006-08-01 | Exxonmobil Chemical Patents Inc. | Catalyst fluidization in oxygenate to olefin reaction systems |
US7619127B2 (en) * | 2003-12-23 | 2009-11-17 | Exxonmobil Chemical Patents Inc. | Method of operating a riser reactor |
US7935857B2 (en) | 2006-03-31 | 2011-05-03 | Exxonmobil Chemical Patents Inc. | Product recovery in gas-solids reactors |
US7799118B2 (en) | 2006-03-31 | 2010-09-21 | Exxonmobil Chemical Patents Inc. | Product recovery in gas-solids reactors |
US7744746B2 (en) | 2006-03-31 | 2010-06-29 | Exxonmobil Research And Engineering Company | FCC catalyst stripper configuration |
US8168842B2 (en) | 2006-05-19 | 2012-05-01 | Shell Oil Company | Process for the alkylation of a cycloalkene |
US8049054B2 (en) | 2006-05-19 | 2011-11-01 | Shell Oil Company | Process for the preparation of C5 and/or C6 olefin |
US8822749B2 (en) | 2007-11-19 | 2014-09-02 | Shell Oil Company | Process for the preparation of an olefinic product |
AU2008327926B2 (en) * | 2007-11-19 | 2011-07-14 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefin |
US8884090B2 (en) | 2007-11-19 | 2014-11-11 | Shell Oil Company | Process for the preparation of an olefin |
WO2009065855A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefin |
AU2008327945B2 (en) * | 2007-11-19 | 2011-08-11 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefinic product |
WO2009065851A1 (en) * | 2007-11-19 | 2009-05-28 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of an olefin |
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EP1257515B1 (en) | 2004-04-14 |
DE60102800T2 (en) | 2005-03-31 |
EP1257515A1 (en) | 2002-11-20 |
AU3975901A (en) | 2001-09-03 |
DE60102800D1 (en) | 2004-05-19 |
CN1404463A (en) | 2003-03-19 |
ES2218398T3 (en) | 2004-11-16 |
CN1190395C (en) | 2005-02-23 |
NO20023910L (en) | 2002-08-16 |
AU780007B2 (en) | 2005-02-24 |
NO20023910D0 (en) | 2002-08-16 |
CA2398387A1 (en) | 2001-08-30 |
ATE264283T1 (en) | 2004-04-15 |
ZA200206527B (en) | 2003-04-24 |
US7232936B1 (en) | 2007-06-19 |
MXPA02008196A (en) | 2003-05-23 |
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