CS270208B2 - Method of aldehydes production by means of olefins' hydroformylation - Google Patents
Method of aldehydes production by means of olefins' hydroformylation Download PDFInfo
- Publication number
- CS270208B2 CS270208B2 CS86264A CS26486A CS270208B2 CS 270208 B2 CS270208 B2 CS 270208B2 CS 86264 A CS86264 A CS 86264A CS 26486 A CS26486 A CS 26486A CS 270208 B2 CS270208 B2 CS 270208B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- reactor
- hydroformylation
- primary
- rhodium
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 154
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 88
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 71
- 150000001299 aldehydes Chemical class 0.000 title description 72
- 238000004519 manufacturing process Methods 0.000 title description 9
- 230000008569 process Effects 0.000 claims abstract description 146
- 239000007788 liquid Substances 0.000 claims abstract description 56
- 239000003054 catalyst Substances 0.000 claims description 90
- 239000007789 gas Substances 0.000 claims description 86
- 239000000047 product Substances 0.000 claims description 58
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 42
- 238000004064 recycling Methods 0.000 claims description 42
- 229910052703 rhodium Inorganic materials 0.000 claims description 42
- 239000010948 rhodium Substances 0.000 claims description 42
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 42
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 41
- 239000003446 ligand Substances 0.000 claims description 41
- 239000006227 byproduct Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 238000009835 boiling Methods 0.000 claims description 21
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 239000011574 phosphorus Substances 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 13
- 230000005494 condensation Effects 0.000 claims description 13
- FSHNFAOXXJLGJE-UHFFFAOYSA-N [Rh].[P] Chemical compound [Rh].[P] FSHNFAOXXJLGJE-UHFFFAOYSA-N 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 239000007859 condensation product Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 5
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 8
- 230000006872 improvement Effects 0.000 abstract description 4
- 235000019256 formaldehyde Nutrition 0.000 abstract description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 39
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 34
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 34
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 23
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 238000010926 purge Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- -1 rhodium-phosphorus compound Chemical class 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000002912 waste gas Substances 0.000 description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-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
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000680714 Rhodine Species 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Saccharide Compounds (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/690,912 US4593127A (en) | 1985-01-11 | 1985-01-11 | Hydroformylation process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS26486A2 CS26486A2 (en) | 1989-10-13 |
| CS270208B2 true CS270208B2 (en) | 1990-06-13 |
Family
ID=24774467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS86264A CS270208B2 (en) | 1985-01-11 | 1986-01-13 | Method of aldehydes production by means of olefins' hydroformylation |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4593127A (de) |
| EP (1) | EP0188246B2 (de) |
| JP (1) | JPS61218546A (de) |
| KR (1) | KR900008107B1 (de) |
| CN (1) | CN1008089B (de) |
| AT (1) | ATE73752T1 (de) |
| AU (1) | AU594034B2 (de) |
| CA (1) | CA1258871A (de) |
| CS (1) | CS270208B2 (de) |
| DE (1) | DE3684335D1 (de) |
| DK (1) | DK11486A (de) |
| ES (1) | ES8701710A1 (de) |
| FI (1) | FI88915C (de) |
| IN (1) | IN166934B (de) |
| YU (1) | YU46163B (de) |
| ZA (1) | ZA86222B (de) |
Families Citing this family (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716250A (en) * | 1986-07-10 | 1987-12-29 | Union Carbide Corporation | Hydroformylation using low volatile/organic soluble phosphine ligands |
| US4871879A (en) * | 1987-10-27 | 1989-10-03 | Hoechst Celanese Corporation | Rhodium recovery from hydroformylation reaction product |
| US5059710A (en) * | 1988-08-05 | 1991-10-22 | Union Carbide Chemicals And Plastics Technology Corporation | Ionic phosphites and their use in homogeneous transition metal catalyzed processes |
| US5113022A (en) * | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| US4947003A (en) * | 1988-11-28 | 1990-08-07 | Virginia Tech Intellectual Properties, Inc. | Process for the hydroformulation of olefinically unsaturated organic reactants using a supported aqueous phase catalyst |
| US5001274A (en) * | 1989-06-23 | 1991-03-19 | Union Carbide Chemicals And Plastics Company Inc. | Hydroformylation process |
| JP2893902B2 (ja) * | 1989-10-19 | 1999-05-24 | 三菱化学株式会社 | オレフィンのヒドロホルミル化法 |
| US5087763A (en) * | 1990-11-09 | 1992-02-11 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| DE4210026A1 (de) * | 1992-03-27 | 1993-09-30 | Hoechst Ag | Decylalkoholgemische, daraus erhältliche Phthalsäureester und ihre Verwendung als Weichmacher |
| GB9312225D0 (en) * | 1993-06-14 | 1993-07-28 | Exxon Chemical Patents Inc | Process and apparatus |
| US5410091A (en) * | 1994-06-02 | 1995-04-25 | Quimica Oxal C.A. | Rhodium catalyzed oxo process in tubular reactor |
| US5600017A (en) * | 1995-01-18 | 1997-02-04 | Exxon Research And Engineering Company | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide hydrogen ethylene and acetylene-(LAW072) |
| US5675041A (en) * | 1995-01-18 | 1997-10-07 | Exxon Research & Engineering Company | Direct hydroformylation of a multi-component synthesis gas containing carbon monoxide, hydrogen, ethylene, and acetylene |
| ZA96178B (en) * | 1995-01-18 | 1997-06-30 | Exxon Chemical Patents Inc | Organic compounds and processes for their manufacture |
| DE19530698A1 (de) * | 1995-08-21 | 1997-02-27 | Basf Ag | Verfahren zur Aufarbeitung eines flüssigen Hydroformylierungsaustrags |
| DE19836807A1 (de) | 1998-08-14 | 2000-02-17 | Basf Ag | Verfahren zur Herstellung von Aldehyden und/oder Alkoholen oder Aminen |
| JP3921853B2 (ja) * | 1998-12-10 | 2007-05-30 | 三菱化学株式会社 | アルデヒド類及びアルコール類の製造方法 |
| DE10108475A1 (de) * | 2001-02-22 | 2002-09-12 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| BRPI0411948B1 (pt) * | 2003-07-03 | 2014-03-25 | Dow Technology Investments Llc | Método para minimizar a produção de um ou mais produtos de degradação de ligantes de íons fosfônio e processo para minimizar a formação de um ou mais produtos de degradação de ligantes de íons fosfônio |
| WO2005058787A1 (en) * | 2003-12-18 | 2005-06-30 | Exxonmobil Chemical Patents Inc. | Improvements in or relating to hydroformylation |
| US7586017B2 (en) | 2003-12-18 | 2009-09-08 | Exxonmobil Chemical Patents Inc. | Hydrogenation |
| US20050209469A1 (en) * | 2004-03-22 | 2005-09-22 | Shutt John R | Converting propylene in an oxygenate-contaminated propylene stream to non-polymerization derivative products |
| IN2007CN00473A (de) | 2004-08-02 | 2007-08-24 | Union Carbide Chem Plastic | |
| BRPI0808297B1 (pt) * | 2007-03-20 | 2017-02-07 | Dow Technology Investments Llc | processo de hidroformilação |
| DE102009016651B4 (de) * | 2009-04-07 | 2011-11-17 | Oxea Gmbh | Verfahren zur Herstellung von Aldehyden |
| US8741173B2 (en) | 2010-10-05 | 2014-06-03 | Dow Technology Investments Llc | Hydroformylation process |
| KR101890961B1 (ko) | 2010-11-12 | 2018-08-22 | 바스프 에스이 | 물 첨가에 의한 히드로포르밀화 방법에서의 오손의 완화 |
| SA112330271B1 (ar) | 2011-04-18 | 2015-02-09 | داو تكنولوجى انفستمنتس ال ال سى | تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء |
| CN102826972B (zh) * | 2011-06-17 | 2015-05-13 | 中国石油化工股份有限公司 | 一种烯烃氢甲酰化反应制备醛的方法 |
| CN102826973B (zh) * | 2011-06-17 | 2015-08-19 | 中国石油化工股份有限公司 | 一种低碳烯烃氢甲酰化制备醛的方法 |
| CA2858351C (en) | 2011-12-20 | 2016-11-22 | Dow Technology Investments Llc | A hydroformylation process |
| JP2013181004A (ja) * | 2012-03-02 | 2013-09-12 | Jnc Corp | オキソ反応触媒寿命改良法 |
| CN104144901B (zh) | 2012-03-07 | 2017-03-01 | 巴斯夫欧洲公司 | C3‑c20醛氢化和蒸馏中的热集成方法 |
| US8889917B2 (en) | 2012-04-12 | 2014-11-18 | Basf Se | Method of supplementing the catalyst in continuous hydroformylation |
| PL2836474T3 (pl) | 2012-04-12 | 2018-06-29 | Basf Se | Sposób uzupełniania katalizatora podczas ciągłego hydroformylowania |
| CN104379258B (zh) | 2012-06-04 | 2017-05-03 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| IN2015DN02639A (de) | 2012-09-25 | 2015-09-18 | Dow Technology Investments Llc | |
| JP6174711B2 (ja) | 2012-12-06 | 2017-08-02 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ヒドロホルミル化方法 |
| US9340480B2 (en) | 2013-04-30 | 2016-05-17 | Oxea Corporation | Aldehyde production process with multi-stage condensation |
| CN104248860A (zh) | 2013-06-27 | 2014-12-31 | 陶氏技术投资有限责任公司 | 热管理方法 |
| CN103520944A (zh) * | 2013-07-30 | 2014-01-22 | 天津渤海化工有限责任公司天津碱厂 | 一种贵金属催化剂循环母液的冷却方法 |
| DE102013225883A1 (de) | 2013-12-13 | 2015-06-18 | Evonik Industries Ag | Zweistufige Hydroformylierung mit Kreisgas- und SILP-Technologie |
| EP3083542A1 (de) | 2013-12-19 | 2016-10-26 | Dow Technology Investments LLC | Hydroformylierungsverfahren |
| CN104725170B (zh) * | 2013-12-19 | 2019-08-23 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
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| US12649805B2 (en) | 2019-11-07 | 2026-06-09 | Eastman Chemical Company | Recycle content poly(vinyl acetal) |
| CN114728869B (zh) | 2019-11-07 | 2024-07-12 | 伊士曼化工公司 | 回收成分丙醇 |
| US11976017B2 (en) | 2019-12-19 | 2024-05-07 | Dow Technology Investments Llc | Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms |
| WO2021211517A1 (en) | 2020-04-13 | 2021-10-21 | Eastman Chemical Company | Liquefying and dehalogenating waste plastics |
| WO2022031436A1 (en) | 2020-08-04 | 2022-02-10 | Eastman Chemical Company | Propionic acid process |
| US12195674B2 (en) | 2021-09-21 | 2025-01-14 | Eastman Chemical Company | Using spent caustic solution from pygas treatment to neutralize halogens from liquified waste plastic |
| CN121039090A (zh) | 2023-05-04 | 2025-11-28 | 陶氏技术投资有限责任公司 | 加氢甲酰化方法 |
| WO2026106685A1 (en) | 2024-11-13 | 2026-05-21 | Dow Technology Investments Llc | Hydroformylation process |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3271458A (en) * | 1962-11-23 | 1966-09-06 | Exxon Research Engineering Co | Cooling and catalyst recycle in oxo synthesis |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| GB1387657A (en) * | 1972-08-25 | 1975-03-19 | Davy Powergas Ltd | Hydroformylation process |
| US4148830A (en) * | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| US4247486A (en) * | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| US4298541A (en) * | 1979-02-12 | 1981-11-03 | Exxon Research & Engineering Co. | Trihydrocarbyl silyl-substituted alkyl diaryl phosphine transition metal complexes and their use as homogeneous catalysts |
| JPS55501178A (de) * | 1979-02-12 | 1980-12-25 | ||
| DE2965158D1 (en) * | 1979-03-21 | 1983-05-11 | Davy Mckee London | Hydroformylation process |
| DE16285T1 (de) * | 1979-03-21 | 1983-04-28 | Davy Mckee (London) Ltd., London | Verfahren zur herstellung von aldehyden durch hydroformylierung von alkenen. |
| US4267383A (en) * | 1979-05-04 | 1981-05-12 | Celanese Corporation | Hydrocarbonylation |
| US4283562A (en) * | 1979-10-26 | 1981-08-11 | Union Carbide Corporation | Hydroformylation process using stable rhodium catalyst |
| DE3102281C2 (de) * | 1980-02-02 | 1982-12-23 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Hydroformylierung von Propylen |
| JPS5828857A (ja) * | 1981-08-12 | 1983-02-19 | Toshiba Corp | 半導体装置 |
| US4400548A (en) * | 1981-08-17 | 1983-08-23 | Union Carbide Corporation | Hydroformylation process using bisphosphine monooxide ligands |
| DE3361212D1 (en) * | 1982-06-11 | 1985-12-19 | Davy Mckee London | Hydroformylation process |
| EP0096986B1 (de) * | 1982-06-11 | 1987-04-22 | DAVY McKEE (LONDON) LIMITED | Hydroformylierungsverfahren |
| EP0096988B1 (de) * | 1982-06-11 | 1987-07-08 | DAVY McKEE (LONDON) LIMITED | Hydroformylierungsverfahren |
| DE3245883A1 (de) * | 1982-12-11 | 1984-06-14 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur hydroformylierung von olefinen |
-
1985
- 1985-01-11 US US06/690,912 patent/US4593127A/en not_active Expired - Lifetime
-
1986
- 1986-01-09 CA CA000499305A patent/CA1258871A/en not_active Expired
- 1986-01-10 AU AU52229/86A patent/AU594034B2/en not_active Ceased
- 1986-01-10 EP EP86100278A patent/EP0188246B2/de not_active Expired - Lifetime
- 1986-01-10 CN CN86101063A patent/CN1008089B/zh not_active Expired
- 1986-01-10 AT AT86100278T patent/ATE73752T1/de not_active IP Right Cessation
- 1986-01-10 YU YU2686A patent/YU46163B/sh unknown
- 1986-01-10 ZA ZA86222A patent/ZA86222B/xx unknown
- 1986-01-10 KR KR1019860000159A patent/KR900008107B1/ko not_active Expired
- 1986-01-10 FI FI860125A patent/FI88915C/fi not_active IP Right Cessation
- 1986-01-10 DE DE8686100278T patent/DE3684335D1/de not_active Expired - Lifetime
- 1986-01-10 DK DK11486A patent/DK11486A/da not_active Application Discontinuation
- 1986-01-10 ES ES550785A patent/ES8701710A1/es not_active Expired
- 1986-01-11 JP JP61004098A patent/JPS61218546A/ja active Pending
- 1986-01-13 CS CS86264A patent/CS270208B2/cs unknown
- 1986-01-22 IN IN39/MAS/86A patent/IN166934B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI860125L (fi) | 1986-07-12 |
| EP0188246A2 (de) | 1986-07-23 |
| FI860125A0 (fi) | 1986-01-10 |
| CA1258871A (en) | 1989-08-29 |
| AU5222986A (en) | 1986-07-17 |
| FI88915B (fi) | 1993-04-15 |
| US4593127A (en) | 1986-06-03 |
| EP0188246B2 (de) | 1996-04-17 |
| FI88915C (fi) | 1993-07-26 |
| EP0188246B1 (de) | 1992-03-18 |
| EP0188246A3 (en) | 1987-05-27 |
| ES550785A0 (es) | 1986-12-01 |
| ZA86222B (en) | 1986-08-27 |
| ES8701710A1 (es) | 1986-12-01 |
| JPS61218546A (ja) | 1986-09-29 |
| YU46163B (sh) | 1993-05-28 |
| CN86101063A (zh) | 1986-08-20 |
| DK11486A (da) | 1986-07-12 |
| AU594034B2 (en) | 1990-03-01 |
| YU2686A (en) | 1988-02-29 |
| CS26486A2 (en) | 1989-10-13 |
| CN1008089B (zh) | 1990-05-23 |
| ATE73752T1 (de) | 1992-04-15 |
| KR900008107B1 (ko) | 1990-10-31 |
| IN166934B (de) | 1990-08-11 |
| DE3684335D1 (en) | 1992-04-23 |
| KR860005772A (ko) | 1986-08-13 |
| DK11486D0 (da) | 1986-01-10 |
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