JP2013508274A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013508274A5 JP2013508274A5 JP2012534224A JP2012534224A JP2013508274A5 JP 2013508274 A5 JP2013508274 A5 JP 2013508274A5 JP 2012534224 A JP2012534224 A JP 2012534224A JP 2012534224 A JP2012534224 A JP 2012534224A JP 2013508274 A5 JP2013508274 A5 JP 2013508274A5
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- ligand
- hydroformylation
- reaction
- contacting
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 claims 12
- 239000003446 ligand Substances 0.000 claims 11
- 230000027455 binding Effects 0.000 claims 10
- 238000007037 hydroformylation reaction Methods 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 239000002184 metal Substances 0.000 claims 6
- 229910052751 metal Inorganic materials 0.000 claims 6
- 230000003197 catalytic Effects 0.000 claims 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M buffer Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000001336 alkenes Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000010574 gas phase reaction Methods 0.000 claims 2
- 150000008301 phosphite esters Chemical class 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000007853 buffer solution Substances 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 230000000977 initiatory Effects 0.000 claims 1
- 239000006193 liquid solution Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000012495 reaction gas Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
Claims (10)
- 少なくとも１種のアルデヒド生成物を製造するためのヒドロホルミル化方法であって、気相反応条件においてヒドロホルミル化触媒の存在下で一酸化炭素、水素及び１種以上のオレフィン系不飽和化合物を接触させることを含み、前記触媒が少なくとも１種のオルガノホスフィットリガンドを含むリガンドと触媒金属を含み、前記触媒が担体上に物理吸着されており、少なくとも一部の時間水蒸気が存在している方法。
- アルデヒドがいくらか形成された後に、追加量のリガンドが触媒と少なくとも１回接触する、請求項１記載の方法。
- アルデヒドがいくらか形成された後に、触媒が緩衝溶液と接触する、請求項１又は２記載の方法。
- 水の量（モル）が触媒金属の量（モル）の少なくとも約0.001倍である、請求項１〜３のいずれか１項に記載の方法。
- 前記リガンドが下式
により表されるオルガノポリホスフィットリガンドを含む、請求項１〜４のいずれか１項に記載の方法。 - 供給流体としてヒドロホルミル化反応器の排流を用いる、請求項１〜５のいずれか１項に記載の方法。
- ヒドロホルミル化反応の開始後に少なくとも１回、追加量のリガンドが反応ゾーンに供給される、請求項１〜６のいずれか１項に記載の方法。
- 少なくとも１種のアルデヒド生成物を連続製造するためのヒドロホルミル化方法であって、連続反応条件においてヒドロホルミル化反応ガス中で、触媒金属及びリガンドＡの錯体を含む触媒金属−リガンド錯体の存在下において１種以上のＣ2-4アキラルオレフィン、一酸化炭素、及び水素を接触させる工程を含み、前記金属がロジウムを含み、前記錯体が担体上に物理吸着されており、前記接触が約−２５℃超、約２００℃未満の温度において、一酸化炭素、水素及びオレフィン反応体を含む総ガス圧が約２５psia(１７２kPa)超、約２０００psia(１３７８９kPa)未満であるように行われ、少なくとも一部の時間水蒸気が存在しており、水の量が１日あたり触媒金属の当量に対して少なくとも約0.001モル当量の水である方法。
- ヒドロホルミル化による少なくとも１種のアルデヒド生成物の製造方法であって、(a)気相反応条件において反応ゾーンにおいて、ヒドロホルミル化触媒の存在下で一酸化炭素、水素及び１種以上のオレフィン系不飽和化合物を接触させること、ここで前記触媒は少なくとも１種のオルガノホスフィットリガンドを含むリガンド及び触媒金属を含む担持された触媒であり、前記触媒は担体に担持されており、反応の活性を実質的に維持するに十分な量の水蒸気が少なくとも一部の時間存在しており、以下の工程の少なくとも１つ、(b)ヒドロホルミル化反応の開始後少なくとも１回、反応ゾーンに追加量のリガンドを加えること、及び(c)担持された触媒を緩衝液と接触させること、を含む方法。
- 前記緩衝液が液体溶液であり、触媒と緩衝液を接触させる前に反応を止め、接触後に前記緩衝液が反応ゾーンから実質的に取り出され、反応が再び開始される、請求項９記載の方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25245009P | 2009-10-16 | 2009-10-16 | |
| US61/252,450 | 2009-10-16 | ||
| PCT/US2010/051576 WO2011046781A1 (en) | 2009-10-16 | 2010-10-06 | Gas phase hydroformylation process |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508274A JP2013508274A (ja) | 2013-03-07 |
| JP2013508274A5 true JP2013508274A5 (ja) | 2013-11-21 |
| JP5823967B2 JP5823967B2 (ja) | 2015-11-25 |
Family
ID=43568184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012534224A Active JP5823967B2 (ja) | 2009-10-16 | 2010-10-06 | 気相ヒドロホルミル化方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8586800B2 (ja) |
| EP (1) | EP2488539B2 (ja) |
| JP (1) | JP5823967B2 (ja) |
| CN (2) | CN107266298A (ja) |
| WO (1) | WO2011046781A1 (ja) |
| ZA (1) | ZA201202751B (ja) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013184350A1 (en) * | 2012-06-04 | 2013-12-12 | Dow Technology Investments Llc | Hydroformylation process |
| DE102013201668B4 (de) | 2013-02-01 | 2019-05-16 | Evonik Degussa Gmbh | Verfahren zur selektiven Ruthenium-katalysierten Hydroaminomethylierung von Olefinen |
| DE102013217174A1 (de) | 2013-08-28 | 2015-03-05 | Evonik Industries Ag | Zusammensetzung und deren Verwendung in Verfahren zur Hydroformylierung von ungesättigten Verbindungen |
| DE102014209533A1 (de) * | 2014-05-20 | 2015-12-17 | Evonik Degussa Gmbh | Gemische von Monophosphitligand und deren Verwendung zur Katalyse einer Hydroformylierungsreaktion |
| CN104475161B (zh) * | 2014-12-03 | 2016-09-14 | 中国石油大学(北京) | 铁磁性纳米颗粒固载铑络合物的氢甲酰化催化剂的制法 |
| EP3029045B1 (de) * | 2014-12-04 | 2018-06-13 | Evonik Degussa GmbH | Bisphosphite die eine 2,3 -Biphenol-Einheit als Zentral-Baustein aufweisen |
| EP3130399B1 (de) | 2015-08-12 | 2021-07-07 | Basf Se | Verfahren zur hydroformylierung von olefinen und/oder alkinen in der gasphase mit einem gemisch aus wasserstoff und kohlenmonoxid in gegenwart von heterogenem katalysator |
| EP3674282B1 (en) | 2017-08-24 | 2021-09-22 | Mitsubishi Chemical Corporation | Bisphosphite compound, catalyst, production method of aldehydes, and production method of alcohol |
| US10654784B2 (en) * | 2018-10-05 | 2020-05-19 | Evonik Operations Gmbh | Process for hydroformylating short-chain olefins in the gas phase |
| JP7414234B2 (ja) | 2019-12-09 | 2024-01-16 | 株式会社小林製作所 | 戸板の自開機構、およびそれを備える引き違い戸板または折戸 |
| EP4074722A1 (de) * | 2021-04-16 | 2022-10-19 | Evonik Operations GmbH | Diphosphite mit einem offenen, 3-methylierten flügelbaustein |
| CN113181966B (zh) * | 2021-04-25 | 2022-08-30 | 中国科学院兰州化学物理研究所 | 一种用于烯烃氢甲酰化反应的碳负载氮配位钴铁双金属催化剂的制备及应用 |
| CN118317834A (zh) * | 2021-12-16 | 2024-07-09 | 陶氏技术投资有限责任公司 | 化合物、包含此类化合物的过渡金属络合物加氢甲酰化催化剂前体组合物和加氢甲酰化方法 |
| WO2023114578A1 (en) * | 2021-12-16 | 2023-06-22 | Dow Technology Investments Llc | Transition metal complex hydroformylation catalyst precuror compositions comprising such compounds, and hydroformylation processes |
| CN114931961B (zh) * | 2022-06-10 | 2024-02-27 | 万华化学集团股份有限公司 | 一种氢甲酰化催化剂及其应用 |
| CN116019116B (zh) * | 2022-12-07 | 2024-01-12 | 孟州农达生化制品有限公司 | 一种农药粉剂及其使用方法 |
Family Cites Families (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3352924A (en) | 1963-01-23 | 1967-11-14 | Exxon Research Engineering Co | Carbonylation reactions |
| US3415906A (en) | 1964-05-29 | 1968-12-10 | Hooker Chemical Corp | Phosphite phospholane and phosphorinane compounds |
| US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US4487972A (en) | 1967-10-02 | 1984-12-11 | Mobil Oil Corporation | Production of oxygenated compounds |
| US3847997A (en) | 1969-06-12 | 1974-11-12 | Phillips Petroleum Co | Hydroformylation process and catalyst |
| US4098727A (en) | 1970-07-23 | 1978-07-04 | Mobil Oil Corporation | Insoluble polymers having functional groups containing chemically bonded Group VIII metal |
| US4045493A (en) | 1975-02-03 | 1977-08-30 | Standard Oil Company (Indiana) | Hydroformylation of olefins |
| US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| US4144191A (en) | 1977-06-06 | 1979-03-13 | The Dow Chemical Company | Amine-resin supported rhodium-cobalt carbonyl bimetallic clusters as novel hydroformylation catalysts |
| US4185038A (en) | 1978-07-14 | 1980-01-22 | Conoco, Inc. | Hydroformylation catalysts containing rhodium (I) or iridium (I) chemically bound directly to inorganic polymers |
| US4386013A (en) | 1981-08-24 | 1983-05-31 | Occidental Research Corporation | Hydroformylation process utilizing novel catalyst |
| US4361711A (en) | 1981-12-18 | 1982-11-30 | The Standard Oil Company | Alcohols from olefins and synthesis gas |
| US4504684A (en) | 1982-01-06 | 1985-03-12 | The Standard Oil Company | Metal coordination polymers as hydroformylation and hydrogenation catalysts |
| GB8334359D0 (en) | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
| US4599206A (en) | 1984-02-17 | 1986-07-08 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4567302A (en) | 1984-07-20 | 1986-01-28 | Angus Chemical | Polymeric quaternary ammonium salts possessing antimicrobial activity and methods for preparation and use thereof |
| US4737588A (en) | 1984-12-28 | 1988-04-12 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4748261A (en) | 1985-09-05 | 1988-05-31 | Union Carbide Corporation | Bis-phosphite compounds |
| US4885401A (en) | 1985-09-05 | 1989-12-05 | Union Carbide Corporation | Bis-phosphite compounds |
| US4668651A (en) | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| US4774361A (en) | 1986-05-20 | 1988-09-27 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
| US5113022A (en) | 1988-08-05 | 1992-05-12 | Union Carbide Chemicals & Plastics Technology Corporation | Ionic phosphites used in homogeneous transition metal catalyzed processes |
| US4861918A (en) * | 1988-08-12 | 1989-08-29 | Union Carbide Corporation | Reactivation of hydroformylation catalysts |
| US5277532A (en) | 1989-07-31 | 1994-01-11 | Cefin S.P.A. | Mechanical acceleration device in can welding machines |
| KR910006419B1 (ko) | 1989-09-25 | 1991-08-24 | 한국과학기술원 | 옥소 반응용 폴리스티렌 담지 로듐 촉매의 제조방법 |
| DE4026406A1 (de) | 1990-08-21 | 1992-02-27 | Basf Ag | Rhodiumhydroformylierungskatalysatoren mit bis-phosphit-liganden |
| US5179055A (en) | 1990-09-24 | 1993-01-12 | New York University | Cationic rhodium bis(dioxaphosphorus heterocycle) complexes and their use in the branched product regioselective hydroformylation of olefins |
| US5183943A (en) | 1991-03-18 | 1993-02-02 | Union Carbide Chemicals & Plastics Technology Corporation | Reactivation of hydroformylation catalysts |
| TW213465B (ja) | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| US5409877A (en) | 1991-08-22 | 1995-04-25 | Director-General Of Agency Of Industrial Science And Technology | Catalyst for producing aldehyde and alcohol from olefin, carbon monoxide and hydrogen |
| DE4204808A1 (de) | 1992-02-18 | 1993-08-19 | Basf Ag | Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern |
| CN1029774C (zh) * | 1992-06-19 | 1995-09-20 | 联合碳化化学品及塑料有限公司 | 铑络合物加氢甲酰化催化剂以及该催化剂的前体组合物 |
| US5312996A (en) | 1992-06-29 | 1994-05-17 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process for producing 1,6-hexanedials |
| US5288918A (en) * | 1992-09-29 | 1994-02-22 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation process |
| US5364950A (en) | 1992-09-29 | 1994-11-15 | Union Carbide Chimicals & Plastics Technology Corporation | Process for stabilizing phosphite ligands in hydroformylation reaction mixtures |
| US5789625A (en) * | 1995-12-06 | 1998-08-04 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5767321A (en) | 1995-12-06 | 1998-06-16 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| AU719941B2 (en) | 1995-12-06 | 2000-05-18 | Union Carbide Chemicals & Plastics Technology Corporation | Improved metal-ligand complex catalyzed processes |
| US5741942A (en) | 1996-11-26 | 1998-04-21 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5874640A (en) | 1996-11-26 | 1999-02-23 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5892119A (en) | 1996-11-26 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5789333A (en) | 1997-03-05 | 1998-08-04 | Iowa State University Research Foundation, Inc. | Catalyst system comprising a first catalyst system tethered to a supported catalyst |
| US6121184A (en) | 1997-07-29 | 2000-09-19 | E. I. Du Pont De Nemours And Company | Supported bis(phosphorus) ligands |
| US6229052B1 (en) * | 1998-05-29 | 2001-05-08 | E. I. Du Pont De Nemours And Company | Hydroformylation of olefins using supported bis(phosphorus) ligands |
| US6090987A (en) | 1998-07-06 | 2000-07-18 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| WO2001014060A2 (en) | 1999-08-25 | 2001-03-01 | Massachusetts Institute Of Technology | Surface-confined catalytic compositions |
| US6420611B1 (en) * | 1999-09-20 | 2002-07-16 | E. I. Du Pont De Nemours And Company | Composition comprising polymeric phosphite |
| US6380421B1 (en) | 1999-09-20 | 2002-04-30 | E. I. Du Pont De Nemours And Company | Multidentate phosphite ligands, catalytic compositions containing such ligands and catalytic processes utilizing such catalytic compositions |
| US6515161B1 (en) * | 1999-09-20 | 2003-02-04 | E. I. Du Pont De Nemours And Company | Hydroformylation process utilizing multidentate phosphite ligands |
| US6294700B1 (en) | 2000-03-15 | 2001-09-25 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6307110B1 (en) | 2000-03-15 | 2001-10-23 | Union Carbide Chemicals & Plastics Technology Corporation | Separation processes |
| US6362354B1 (en) | 2000-11-17 | 2002-03-26 | E. I. Du Pont De Nemours And Company | Phosphonite ligands, catalyst compositions and hydroformylation process utilizing same |
| US6437192B1 (en) | 2000-11-17 | 2002-08-20 | E. I. Du Pont De Nmeours And Company | Hydroformylation of conjugated dienes to alkenals using phosphonite ligands |
| DE10220799A1 (de) * | 2002-05-10 | 2003-12-11 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von C13-Alkoholgemischen |
| DE10251262A1 (de) * | 2002-11-04 | 2004-05-13 | Basf Ag | Verfahren zur Herstellung von Aldehyden aus Alkanen |
-
2010
- 2010-10-06 WO PCT/US2010/051576 patent/WO2011046781A1/en active Application Filing
- 2010-10-06 US US13/499,317 patent/US8586800B2/en active Active
- 2010-10-06 CN CN201710599890.6A patent/CN107266298A/zh active Pending
- 2010-10-06 CN CN2010800468045A patent/CN102574878A/zh active Pending
- 2010-10-06 JP JP2012534224A patent/JP5823967B2/ja active Active
- 2010-10-06 EP EP10765548.2A patent/EP2488539B2/en active Active
-
2012
- 2012-04-16 ZA ZA2012/02751A patent/ZA201202751B/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2013508274A5 (ja) | ||
| Sindhu et al. | Recent developments and applications of the Cadiot–Chodkiewicz reaction | |
| JP7085544B2 (ja) | ヒドロホルミル化触媒溶液を処理する方法 | |
| JP5496188B2 (ja) | ヒドロホルミル化によりｃ４−含有炭化水素流から１−ブテンを分離する方法 | |
| KR930003936B1 (ko) | 알데히드의 제조공정 | |
| JP2012522048A5 (ja) | ||
| TW201235100A (en) | Use of supported ionic liquid phase (SILP) catalyst systems in the hydroformylation of olefin-containing mixtures to aldehyde mixtures with a high content of aldehydes unbranched in the 2 position | |
| RU2011143929A (ru) | Способ гидроформилирования с помощью двойного открыто-концевого бисфосфитного лиганда | |
| CN109311793B (zh) | 用于生产醛的催化剂和方法 | |
| JP2013521246A5 (ja) | ||
| JP2021536469A (ja) | 含酸素化合物生成のための移動ヒドロホルミル化 | |
| TWI414506B (zh) | 藉由氫化二聚合作用製備雙烯類之方法 | |
| JP2019534151A (ja) | 失活ヒドロホルミル化触媒溶液を再生する方法 | |
| JP2014502254A5 (ja) | ||
| JP7291142B2 (ja) | １－アシルオキシ－２－メチル－２－プロペンの製造方法 | |
| RU2352552C1 (ru) | Катализатор гидроформилирования олефинов c2-c20, способ его получения (варианты) и способ получения альдегидов c3-c21 | |
| EP0001937B1 (en) | Process for the hydrocarbonylation of methanol to ethanol in the presence of an inert liquid | |
| Horiguchi et al. | Palladium/Phosphite or Phosphate Catalyzed Oxidative Coupling of Arylboronic Acids with Alkynes to Produce 1, 4‐Diaryl‐1, 3‐butadienes | |
| JP7447116B2 (ja) | ヒドロホルミル化プロセス | |
| JPS582932B2 (ja) | ブチルアルデヒドの製造法 | |
| TW202016062A (zh) | １，３－二醯氧基－２－亞甲基丙烷之製造方法 | |
| JP2012517339A5 (ja) | ||
| JP2006306815A (ja) | アルデヒドの製造方法 | |
| TW200418785A (en) | Process for preparing aldehydes by hydroformylation of olefinically unsaturated compounds, catalyzed by unmodified complexes of metals of groups 8 to 10 of the PTE in the presence of cyclic carbonic esters | |
| JPH092979A (ja) | 遷移金属錯体をベースとする触媒組成物によるオレフィンの二重結合の移動方法 |