CN1204096C - 丙烯和己烯的可变制备方法 - Google Patents
丙烯和己烯的可变制备方法 Download PDFInfo
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- CN1204096C CN1204096C CNB011173947A CN01117394A CN1204096C CN 1204096 C CN1204096 C CN 1204096C CN B011173947 A CNB011173947 A CN B011173947A CN 01117394 A CN01117394 A CN 01117394A CN 1204096 C CN1204096 C CN 1204096C
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- ethene
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- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000008521 reorganization Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000005872 self-metathesis reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000010555 transalkylation reaction Methods 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
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- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/107—Alkenes with six carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/02—Alkenes
- C07C11/06—Propene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G70/00—Working-up undefined normally gaseous mixtures obtained by processes covered by groups C10G9/00, C10G11/00, C10G15/00, C10G47/00, C10G51/00
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
- C07C2523/32—Manganese, technetium or rhenium
- C07C2523/36—Rhenium
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- 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
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/42—Platinum
-
- 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
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
-
- 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
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- 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)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10013253A DE10013253A1 (de) | 2000-03-17 | 2000-03-17 | Verfahren zur flexiblen Herstellung von Propen und Hexen |
| DE10013253.7 | 2000-03-17 |
Publications (2)
| Publication Number | Publication Date |
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| CN1339426A CN1339426A (zh) | 2002-03-13 |
| CN1204096C true CN1204096C (zh) | 2005-06-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB011173947A Expired - Fee Related CN1204096C (zh) | 2000-03-17 | 2001-03-17 | 丙烯和己烯的可变制备方法 |
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| EP (1) | EP1134271B1 (enExample) |
| JP (1) | JP4749577B2 (enExample) |
| CN (1) | CN1204096C (enExample) |
| DE (2) | DE10013253A1 (enExample) |
| ES (1) | ES2345317T3 (enExample) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10039995A1 (de) * | 2000-08-11 | 2002-02-21 | Basf Ag | Verfahren zur Herstellung von Alkylarylsulfonaten |
| EP1942090B1 (en) * | 2001-01-25 | 2013-10-23 | Lummus Technology Inc. | Process for the production of hexene-1 and ethylene |
| US20050124839A1 (en) * | 2001-06-13 | 2005-06-09 | Gartside Robert J. | Catalyst and process for the metathesis of ethylene and butene to produce propylene |
| US6777582B2 (en) * | 2002-03-07 | 2004-08-17 | Abb Lummus Global Inc. | Process for producing propylene and hexene from C4 olefin streams |
| US7214841B2 (en) * | 2003-07-15 | 2007-05-08 | Abb Lummus Global Inc. | Processing C4 olefin streams for the maximum production of propylene |
| EP1678113B1 (de) * | 2003-10-21 | 2008-07-16 | Basf Se | Verfahren zur kontinuierlichen herstellung von aldehyden |
| DE102004009805A1 (de) * | 2004-02-28 | 2005-09-15 | Basf Ag | Trägerkatalysator definierter Porenverteilung im Bereich der Mesoporen |
| FR2872509B1 (fr) * | 2004-07-02 | 2006-09-22 | Cpe Lyon Fcr | Procede de metathese de composes comportant une double liaison olefinique, notamment d'olefines |
| FR2872510B1 (fr) * | 2004-07-02 | 2006-09-08 | Cpe Lyon Fcr | Procede de transformation d'ethylene en propylene |
| DE102004049940A1 (de) | 2004-10-13 | 2006-04-20 | Basf Ag | Verfahren zur Herstellung eines C4-Olefin-Gemisches durch Selektivhydrierung und Metatheseverfahren zur Verwendung dieses Stroms |
| JP4736392B2 (ja) * | 2004-10-14 | 2011-07-27 | 三菱化学株式会社 | アルデヒドの製造方法 |
| US20060129013A1 (en) * | 2004-12-09 | 2006-06-15 | Abazajian Armen N | Specific functionalization and scission of linear hydrocarbon chains |
| DE102005009596A1 (de) * | 2005-02-28 | 2006-08-31 | Basf Ag | Verfahren zur Metathese umfassend die Reinigung der Ausgangsstoffe |
| DE102005009665A1 (de) * | 2005-02-28 | 2006-08-31 | Basf Ag | Verfahren zur Herstellung von Propen aus 2-Buten- und Isobuten-reichen Feedströmen |
| CN101172926B (zh) * | 2006-11-02 | 2010-12-22 | 中国石油化工股份有限公司 | 丙烯的增产方法 |
| US20080154077A1 (en) * | 2006-12-21 | 2008-06-26 | Bozzano Andrea G | Oxygenate conversion to olefins with metathesis |
| US7528290B2 (en) * | 2006-12-28 | 2009-05-05 | Uop Llc | Apparatuses and methods for separating butene-1 from a mixed C4 feed |
| JP5255325B2 (ja) * | 2008-05-21 | 2013-08-07 | 旭化成ケミカルズ株式会社 | 粗プロパン及び／又は粗プロピレンの精製方法並びに精製装置 |
| CA2733890C (en) | 2008-08-12 | 2013-10-01 | Lummus Technology Inc. | Integrated propylene production |
| JP5816088B2 (ja) | 2008-09-04 | 2015-11-18 | ラムス テクノロジー インク | オレフィン異性化およびメタセシス触媒 |
| US7982086B2 (en) * | 2009-02-03 | 2011-07-19 | Catalytic Distillation Technologies | Deisobutenizer |
| US8258357B2 (en) * | 2009-03-25 | 2012-09-04 | Lummus Technology Inc. | Production of propylene from butane |
| US8586813B2 (en) | 2009-07-21 | 2013-11-19 | Lummus Technology Inc. | Catalyst for metathesis of ethylene and 2-butene and/or double bond isomerization |
| US8440871B2 (en) * | 2010-03-30 | 2013-05-14 | Uop Llc | Tetramer production apparatus and process relating thereto |
| US8722950B2 (en) | 2010-04-26 | 2014-05-13 | Saudi Basic Industries Corporation | Process for producing propylene and aromatics from butenes by metathesis and aromatization |
| DE102011001587B4 (de) * | 2010-08-05 | 2016-12-29 | Flagsol Gmbh | Verfahren zum Aufbereiten eines Wärmeträgermediums eines solarthermischen Kraftwerks |
| US8674155B2 (en) * | 2010-12-22 | 2014-03-18 | Kellogg Brown & Root, Llc | Systems and methods for processing hydrocarbons |
| WO2013034689A1 (en) * | 2011-09-07 | 2013-03-14 | Shell Internationale Research Maatschappij B.V. | Process for preparing ethylene and/or propylene and an iso-olefin-depleted olefinic product |
| GB201116801D0 (en) | 2011-09-29 | 2011-11-09 | Johnson Matthey Plc | Purification process |
| JP6366587B2 (ja) | 2012-09-14 | 2018-08-01 | ラマス テクノロジー インコーポレイテッド | ほとんど又は全くエチレンを用いないメタセシスを介するプロピレン |
| CN103772095B (zh) * | 2012-10-25 | 2015-09-09 | 中国石油化工股份有限公司 | 丁烯歧化制己烯的方法 |
| MX2015013670A (es) | 2013-03-28 | 2016-02-18 | Procter & Gamble | Composiciones de limpieza que contiene una polieteramina. |
| CN104437525B (zh) * | 2013-09-24 | 2017-01-04 | 中国石油化工股份有限公司 | 歧化催化剂 |
| US9701913B2 (en) * | 2013-12-17 | 2017-07-11 | Uop Llc | Fluid catalytic cracking process including adsorption of hydrogen and a catalyst for the process |
| EP3122849B1 (en) | 2014-03-27 | 2021-07-21 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
| US20150275143A1 (en) | 2014-03-27 | 2015-10-01 | The Procter & Gamble Company | Cleaning compositions containing a polyetheramine |
| EP3152288A1 (en) | 2014-06-06 | 2017-04-12 | The Procter & Gamble Company | Detergent composition comprising polyalkyleneimine polymers |
| WO2016032993A1 (en) | 2014-08-27 | 2016-03-03 | The Procter & Gamble Company | Detergent composition comprising a cationic polymer |
| WO2016032995A1 (en) | 2014-08-27 | 2016-03-03 | The Procter & Gamble Company | Method of treating a fabric |
| WO2016032992A1 (en) | 2014-08-27 | 2016-03-03 | The Procter & Gamble Company | Detergent composition comprising a cationic polymer |
| EP3186349B1 (en) | 2014-08-27 | 2019-09-25 | The Procter and Gamble Company | Detergent composition comprising a cationic polymer |
| JP6430632B2 (ja) | 2014-09-25 | 2018-11-28 | ザ プロクター アンド ギャンブル カンパニー | ポリエーテルアミンを含有する布地ケア組成物 |
| JP6533589B2 (ja) * | 2014-10-28 | 2019-06-19 | エスエムエイチ カンパニー，リミテッド | 混合金属酸化物−ゼオライト担体上のメタセシス触媒およびそれを使用するためのプロセス |
| EP3317236B1 (en) | 2015-07-02 | 2019-09-18 | Saudi Arabian Oil Company | Methods for producing propylene |
| CN109364983A (zh) | 2015-07-02 | 2019-02-22 | 沙特阿拉伯石油公司 | 用于丙烯生产的双重催化剂体系 |
| EP3317237B1 (en) | 2015-07-02 | 2024-09-25 | Saudi Arabian Oil Company | Systems and methods for producing propylene |
| US10329225B2 (en) | 2017-01-20 | 2019-06-25 | Saudi Arabian Oil Company | Dual catalyst processes and systems for propylene production |
| US10934231B2 (en) | 2017-01-20 | 2021-03-02 | Saudi Arabian Oil Company | Multiple-stage catalyst systems and processes for propene production |
| US10550048B2 (en) | 2017-01-20 | 2020-02-04 | Saudi Arabian Oil Company | Multiple-stage catalyst system for self-metathesis with controlled isomerization and cracking |
| WO2019220257A1 (en) * | 2018-05-18 | 2019-11-21 | Sabic Global Technologies B.V. | Method of producing a fuel additive with a hydration unit |
| US10961171B2 (en) | 2018-10-10 | 2021-03-30 | Saudi Arabian Oil Company | Catalysts systems that include metal co-catalysts for the production of propylene |
| US11242299B2 (en) | 2018-10-10 | 2022-02-08 | Saudi Arabian Oil Company | Catalyst systems that include metal oxide co-catalysts for the production of propylene |
| KR102804988B1 (ko) | 2019-03-08 | 2025-05-12 | 사빅 글로벌 테크놀러지스 비.브이. | 연료 첨가제의 제조 방법 |
| US11517892B2 (en) | 2019-12-03 | 2022-12-06 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US11311869B2 (en) | 2019-12-03 | 2022-04-26 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US11339332B2 (en) | 2020-01-29 | 2022-05-24 | Saudi Arabian Oil Company | Systems and processes integrating fluidized catalytic cracking with metathesis for producing olefins |
| US11572516B2 (en) | 2020-03-26 | 2023-02-07 | Saudi Arabian Oil Company | Systems and processes integrating steam cracking with dual catalyst metathesis for producing olefins |
| CN115427378A (zh) | 2020-04-22 | 2022-12-02 | 利安德化学技术有限公司 | 由丁烯生产专用丙烯 |
| EP4214182A1 (en) | 2020-09-15 | 2023-07-26 | Lyondell Chemical Technology, L.P. | Process for converting raffinate butenes to propylene |
| US11679378B2 (en) | 2021-02-25 | 2023-06-20 | Saudi Arabian Oil Company | Methods of producing isomerization catalysts |
| US20240343708A1 (en) | 2021-08-10 | 2024-10-17 | Nippon Shokubai Co., Ltd. | Polyalkylene-oxide-containing compound |
| US11845705B2 (en) | 2021-08-17 | 2023-12-19 | Saudi Arabian Oil Company | Processes integrating hydrocarbon cracking with metathesis for producing propene |
| WO2023022828A1 (en) * | 2021-08-20 | 2023-02-23 | Exxonmobil Chemical Patents Inc. | Metathesis of c4/c5 to propylene and 1-hexene |
| WO2025083637A1 (en) * | 2023-10-18 | 2025-04-24 | Sabic Global Technologies B.V. | Systems and methods for butene metathesis to produce propene and hex-1-ene |
| WO2025114973A1 (en) * | 2023-11-30 | 2025-06-05 | Sabic Global Technologies B.V. | Systems and methods for metathesis of mixed butene and butane feedstocks and recovery and recycle of reactive compounds |
| WO2025141045A1 (en) * | 2023-12-27 | 2025-07-03 | Sabic Global Technologies B.V. | Systems and methods for the production of propene with ethene being substantially absent as a co-feed |
| WO2025141047A1 (en) * | 2023-12-28 | 2025-07-03 | Sabic Global Technologies B.V. | Systems and methods for the production of propene using metathesis reactions |
| WO2025146438A1 (en) * | 2024-01-02 | 2025-07-10 | Sabic Global Technologies B.V. | Systems and methods of producing olefins products using alternate upstream and downstream separation processes at low-temperature metathesis conditions |
Family Cites Families (8)
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| EP0304515B1 (en) * | 1983-03-10 | 1991-12-04 | The Dow Chemical Company | A process for the disproportionation of alkenes |
| US5057638A (en) | 1990-06-22 | 1991-10-15 | Chevron Research And Technology Company | Process for making 1-hexene from 1-butene |
| FR2733978B1 (fr) | 1995-05-11 | 1997-06-13 | Inst Francais Du Petrole | Procede et installation pour la conversion de coupes c4 et c5 olefiniques en ether et en propylene |
| EP0832867B1 (de) * | 1996-09-27 | 2000-01-05 | Basf Aktiengesellschaft | Verfahren zur Herstellung von Propen |
| DE19746040A1 (de) * | 1997-10-17 | 1999-04-22 | Basf Ag | Verfahren zur Herstellung von Propen |
| DE19805716A1 (de) * | 1998-02-12 | 1999-08-19 | Basf Ag | Verfahren zur Herstellung von Propen und gegebenenfalls 1-Buten |
| DE19813720A1 (de) * | 1998-03-27 | 1999-09-30 | Basf Ag | Verfahren zur Herstellung von Olefinen |
| DE19932060A1 (de) | 1999-07-12 | 2001-01-18 | Basf Ag | Verfahren zur Herstellung von C¶5¶-/C¶6¶-Olefinen |
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2000
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2001
- 2001-03-12 US US09/803,147 patent/US6580009B2/en not_active Expired - Lifetime
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- 2001-03-13 ES ES01105437T patent/ES2345317T3/es not_active Expired - Lifetime
- 2001-03-14 JP JP2001072595A patent/JP4749577B2/ja not_active Expired - Fee Related
- 2001-03-17 CN CNB011173947A patent/CN1204096C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1134271A2 (de) | 2001-09-19 |
| EP1134271B1 (de) | 2010-05-19 |
| DE50115484D1 (de) | 2010-07-01 |
| ES2345317T3 (es) | 2010-09-21 |
| DE10013253A1 (de) | 2001-09-20 |
| JP4749577B2 (ja) | 2011-08-17 |
| US6580009B2 (en) | 2003-06-17 |
| CN1339426A (zh) | 2002-03-13 |
| EP1134271A3 (de) | 2003-03-12 |
| JP2001302562A (ja) | 2001-10-31 |
| US20020002317A1 (en) | 2002-01-03 |
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