JP2013515063A5 - - Google Patents
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- Publication number
- JP2013515063A5 JP2013515063A5 JP2012546047A JP2012546047A JP2013515063A5 JP 2013515063 A5 JP2013515063 A5 JP 2013515063A5 JP 2012546047 A JP2012546047 A JP 2012546047A JP 2012546047 A JP2012546047 A JP 2012546047A JP 2013515063 A5 JP2013515063 A5 JP 2013515063A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction zone
- olefinically unsaturated
- unsaturated compound
- catalyst
- ratio
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000003446 ligand Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000007037 hydroformylation reaction Methods 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 2
- RMLOZYVMENRVSS-UHFFFAOYSA-N formaldehyde;rhodium Chemical compound [Rh].O=C RMLOZYVMENRVSS-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28914909P | 2009-12-22 | 2009-12-22 | |
| US61/289,149 | 2009-12-22 | ||
| PCT/US2010/060523 WO2011087696A1 (en) | 2009-12-22 | 2010-12-15 | Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the olefin partial pressure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013515063A JP2013515063A (ja) | 2013-05-02 |
| JP2013515063A5 true JP2013515063A5 (enExample) | 2014-02-06 |
| JP5912084B2 JP5912084B2 (ja) | 2016-04-27 |
Family
ID=43778450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012546047A Active JP5912084B2 (ja) | 2009-12-22 | 2010-12-15 | オレフィン分圧の制御による、混合リガンドヒドロホルミル化プロセスにおけるノルマル：イソアルデヒド比の制御 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8664451B2 (enExample) |
| EP (2) | EP2581362B1 (enExample) |
| JP (1) | JP5912084B2 (enExample) |
| CN (2) | CN102741209B (enExample) |
| TW (1) | TWI518064B (enExample) |
| WO (1) | WO2011087696A1 (enExample) |
| ZA (1) | ZA201204576B (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2942343B1 (en) * | 2009-12-22 | 2019-09-04 | Dow Technology Investments LLC | Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process |
| CN102741209B (zh) † | 2009-12-22 | 2014-12-03 | 陶氏技术投资有限责任公司 | 通过控制烯烃分压来控制混合配体加氢甲酰化工艺中的正构∶异构醛比率 |
| BR112015003762B1 (pt) * | 2012-08-29 | 2021-04-13 | Dow Technology Investments Llc | Processo para a formação de um catalisador de hidroformilação |
| DE102014209533A1 (de) | 2014-05-20 | 2015-12-17 | Evonik Degussa Gmbh | Gemische von Monophosphitligand und deren Verwendung zur Katalyse einer Hydroformylierungsreaktion |
| DE102015202722A1 (de) | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Verfahren zur katalytischen Herstellung von Aldehyden aus Olefinen unter Einsatz von Monophosphit-Gemischen |
| DE102014209536A1 (de) | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Herstellung qualitativ hochwertiger Oxo-Alkohole aus unsteten Rohstoffquellen |
| RU2562971C1 (ru) * | 2014-10-10 | 2015-09-10 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") | Способ непрерывного гидроформилирования олефинов с3-с21 в альдегиды |
| RU2584952C1 (ru) * | 2015-03-26 | 2016-05-20 | Общество с ограниченной ответственностью "Объединенный центр исследований и разработок" (ООО "РН-ЦИР") | Гидрид-карбонильный полифосфитный комплекс родия со смешанными фосфорорганическими лигандами для катализа процесса гидроформилирования олефинов |
| KR102092803B1 (ko) * | 2016-01-13 | 2020-03-24 | 주식회사 엘지화학 | 인계 리간드를 포함하는 촉매 조성물을 이용한 하이드로포밀화 방법 |
| RU2751511C9 (ru) * | 2016-02-11 | 2021-08-18 | Дау Текнолоджи Инвестментс Ллк | Способы превращения олефинов в спирты, простые эфиры или их комбинации |
| KR102131788B1 (ko) | 2017-05-29 | 2020-07-09 | 주식회사 엘지화학 | 히드로포밀화 반응용 촉매 조성물 및 이를 이용한 알데히드 제조방법 |
| CN109311002B (zh) * | 2017-05-29 | 2021-12-10 | Lg化学株式会社 | 用于加氢甲酰化反应的催化剂组合物和使用其制备醛的方法 |
| BR112020022070B1 (pt) | 2018-05-30 | 2023-09-26 | Dow Technology Investments Llc | Método para controlar um processo de hidroformilação para produzir aldeídos |
| CN120271422A (zh) | 2018-05-30 | 2025-07-08 | 陶氏技术投资有限责任公司 | 在加氢甲酰化过程中减缓催化剂失活和/或减缓四膦配位体使用的方法 |
| MY207749A (en) | 2018-05-30 | 2025-03-16 | Dow Technology Investments Llc | Catalyst composition comprising the combination of a monophopsphine, a tetraphosphine ligand and a hydroformylation process using it |
| WO2021126421A1 (en) | 2019-12-19 | 2021-06-24 | Dow Technology Investments Llc | Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms |
| JP7707517B2 (ja) * | 2020-06-02 | 2025-07-15 | 三菱ケミカル株式会社 | アルデヒドの製造方法 |
| MX2023010493A (es) * | 2021-03-31 | 2023-09-18 | Dow Technology Investments Llc | Procesos de hidroformilacion. |
| CN113402367A (zh) * | 2021-06-16 | 2021-09-17 | 上海华谊（集团）公司 | 连续氢甲酰化反应中调节正异比的方法 |
| GB202213997D0 (en) * | 2022-09-26 | 2022-11-09 | Johnson Matthey Davy Technologies Ltd | Parallel zone hydroformylation reaction |
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| 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 |
| 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 |
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| GB8334359D0 (en) | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
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| US4835299A (en) | 1987-03-31 | 1989-05-30 | Union Carbide Corporation | Process for purifying tertiary organophosphites |
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| US4873213A (en) * | 1988-08-12 | 1989-10-10 | Puckette Thomas A | Low pressure rhodium catalyzed hydroformylation of olefins |
| US5114473A (en) | 1988-08-25 | 1992-05-19 | Union Carbide Chemicals And Plastics Technology Corporation | Transition metal recovery |
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| KR100596365B1 (ko) | 2004-06-12 | 2006-07-03 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| KR100547587B1 (ko) | 2004-06-12 | 2006-01-31 | 주식회사 엘지화학 | 인을 포함하는 촉매 조성물 및 이를 이용한히드로포르밀화 방법 |
| CA2575122C (en) | 2004-08-02 | 2013-06-25 | Union Carbide Chemicals & Plastics Technology Corporation | Stabilization of a hydroformylation process |
| DE102004055832A1 (de) * | 2004-11-19 | 2006-06-01 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von Aldehyden |
| ZA200804818B (en) † | 2005-12-15 | 2009-11-25 | Penn State Res Found | Tetraphosphorus ligands for catalytic hydroformylation and related reactions |
| US7586010B2 (en) * | 2006-12-21 | 2009-09-08 | Eastman Chemical Company | Phosphonite-containing catalysts for hydroformylation processes |
| MY146608A (en) | 2007-03-20 | 2012-09-14 | Dow Technology Investments Llc | Hydroformylation process with improved control over product isomers |
| JP5298119B2 (ja) * | 2007-04-09 | 2013-09-25 | エルジー・ケム・リミテッド | ホスファイト配位子を含む触媒組成物およびこれを用いたヒドロホルミル化方法 |
| CN101293818B (zh) | 2007-04-28 | 2010-07-07 | 中国石油化工股份有限公司 | 混合丁烯氢甲酰化的两段反应方法 |
| CN101565353B (zh) | 2008-04-25 | 2013-01-02 | 中国石油化工股份有限公司 | 一种2-丙基庚醇的制备方法 |
| CN102741209B (zh) † | 2009-12-22 | 2014-12-03 | 陶氏技术投资有限责任公司 | 通过控制烯烃分压来控制混合配体加氢甲酰化工艺中的正构∶异构醛比率 |
| EP2942343B1 (en) † | 2009-12-22 | 2019-09-04 | Dow Technology Investments LLC | Controlling the normal : iso aldehyde ratio in a mixed ligand hydroformylation process |
| EP2722325B2 (en) † | 2009-12-22 | 2019-01-16 | Dow Technology Investments LLC | Controlling the normal:iso aldehyde ratio in a mixed ligand hydroformylation process by controlling the syngas partial pressure |
-
2010
- 2010-12-15 CN CN201080062976.1A patent/CN102741209B/zh active Active
- 2010-12-15 US US13/517,419 patent/US8664451B2/en active Active
- 2010-12-15 CN CN201410199317.2A patent/CN103951550B/zh active Active
- 2010-12-15 JP JP2012546047A patent/JP5912084B2/ja active Active
- 2010-12-15 EP EP13150016.7A patent/EP2581362B1/en active Active
- 2010-12-15 WO PCT/US2010/060523 patent/WO2011087696A1/en not_active Ceased
- 2010-12-15 EP EP10795186.5A patent/EP2516371B2/en active Active
- 2010-12-21 TW TW099144935A patent/TWI518064B/zh active
-
2012
- 2012-06-20 ZA ZA2012/04576A patent/ZA201204576B/en unknown
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