ES2560112T3 - Procedimiento para la preparación de compuestos de carbonilo olefínicamente insaturados mediante deshidrogenación oxidativa de alcoholes - Google Patents
Procedimiento para la preparación de compuestos de carbonilo olefínicamente insaturados mediante deshidrogenación oxidativa de alcoholes Download PDFInfo
- Publication number
- ES2560112T3 ES2560112T3 ES09715510.5T ES09715510T ES2560112T3 ES 2560112 T3 ES2560112 T3 ES 2560112T3 ES 09715510 T ES09715510 T ES 09715510T ES 2560112 T3 ES2560112 T3 ES 2560112T3
- Authority
- ES
- Spain
- Prior art keywords
- olefinically unsaturated
- alcohols
- preparation
- unsaturated carbonyl
- carbonyl compounds
- 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.)
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- 150000001298 alcohols Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001728 carbonyl compounds Chemical class 0.000 title 1
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 title 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910000323 aluminium silicate Inorganic materials 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 229960001545 hydrotalcite Drugs 0.000 claims 1
- 229910001701 hydrotalcite Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229910000510 noble metal Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Procedimiento para la preparación de compuestos de carbonilo olefínicamente insaturados de fórmula general I**Fórmula** en la que R1 es hidrógeno cuando R2 representa un resto de fórmula II**Fórmula** o R1 y R2 juntos significan un resto de fórmula general III**Fórmula** en la que R3, R4, R5 y R6 en cada caso representan independientemente entre sí hidrógeno, un grupo alquilo C1 - C18, un grupo cicloalquilo C5 - C18 dado el caso sustituido, o un grupo arilo C6 - C18 dado el caso sustituido y los átomos de anillo de los grupos cicloalquilo y arilo pueden estar sustituidos parcialmente por heteroátomos, seleccionados por N, O y S, mediante reacción de alcoholes de fórmula general IV**Fórmula** en la que R1, R2 y R3 tienen el significado mencionado anteriormente, mediante deshidrogenación oxidativa en atmósfera que contiene oxígeno en un catalizador que contiene oro, caracterizado porque como catalizador que contiene oro se usa un catalizador soportado que contiene oro o una mezcla de oro y metales nobles seleccionados de Cu, Ag, Pd, Pt, Rh, Ru, W o Os, la reacción se realiza a temperaturas en el intervalo de 50 ºC a 240 ºC y en presencia de aire, peróxido de hidrógeno o un gas o una mezcla de gases con un contenido de oxígeno en el intervalo del 7 % al 30 % en volumen como atmósfera que contiene oxígeno, en donde como material de soporte se usa óxido de aluminio, un aluminosilicato o una hidrotalcita o sus mezclas.
Description
Claims (1)
-
imagen1 carbonilo olefínicamente insaturados de fórmula general I en presencia de aire, peróxido de hidrógeno o un gas o una mezcla de gases con un contenido de oxígeno del 7 % al 30 % en volumen a temperaturas en el intervalo de 50 ºC a 240 ºC, usándose como material de soporte óxido de aluminio, un aluminosilicato o una hidrotalcita o sus mezclas.7
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102008011767A DE102008011767B4 (de) | 2008-02-28 | 2008-02-28 | Verfahren zur Herstellung von olefinisch ungesättigten Carbonylverbindungen durch oxidative Dehydrierung von Alkoholen |
| DE102008011767 | 2008-02-28 | ||
| PCT/EP2009/052383 WO2009106621A1 (de) | 2008-02-28 | 2009-02-27 | Verfahren zur herstellung von olefinisch ungesättigten carbonylverbindungen durch oxidative dehydrierung von alkoholen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2560112T3 true ES2560112T3 (es) | 2016-02-17 |
Family
ID=40810276
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09715609T Active ES2371324T3 (es) | 2008-02-28 | 2009-02-27 | Procedimiento para la isomerización de alcoholes olefínicamente insaturados. |
| ES09715510.5T Active ES2560112T3 (es) | 2008-02-28 | 2009-02-27 | Procedimiento para la preparación de compuestos de carbonilo olefínicamente insaturados mediante deshidrogenación oxidativa de alcoholes |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09715609T Active ES2371324T3 (es) | 2008-02-28 | 2009-02-27 | Procedimiento para la isomerización de alcoholes olefínicamente insaturados. |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US8410315B2 (es) |
| EP (2) | EP2257513B1 (es) |
| JP (2) | JP5470277B2 (es) |
| CN (2) | CN101959837B (es) |
| AT (1) | ATE520636T1 (es) |
| CA (2) | CA2715655A1 (es) |
| DE (1) | DE102008011767B4 (es) |
| ES (2) | ES2371324T3 (es) |
| MX (2) | MX2010009123A (es) |
| WO (2) | WO2009106621A1 (es) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010076182A1 (de) | 2008-12-30 | 2010-07-08 | Basf Se | Verfahren zur herstellung von ketonen durch umsetzung von 1,1-disubstituierten olefinen mit n2o |
| CN102470346B (zh) * | 2009-07-02 | 2015-07-08 | 巴斯夫欧洲公司 | 用于氧化脱氢或环氧化的负载型含贵金属催化剂 |
| EP2597081A1 (en) | 2011-11-25 | 2013-05-29 | Basf Se | Process for preparing 3-substituted 2-alkenals, in particular prenal |
| JP6103583B2 (ja) * | 2012-03-13 | 2017-03-29 | 国立大学法人北陸先端科学技術大学院大学 | 金及びパラジウムを含む高分子保護ナノ粒子担持ハイドロタルサイト触媒、並びにその製造方法及び使用 |
| JP6345189B2 (ja) * | 2013-01-23 | 2018-06-20 | フイルメニツヒ ソシエテ アノニムFirmenich Sa | 4−メチルペント−3−エン−1−オール誘導体の製造方法 |
| CN103861633B (zh) * | 2014-02-24 | 2015-11-25 | 万华化学集团股份有限公司 | 一种非均相催化剂及其制备方法及利用该催化剂制备3-甲基-2-丁烯-1-醇的方法 |
| JP6532055B2 (ja) * | 2015-03-30 | 2019-06-19 | 国立大学法人北陸先端科学技術大学院大学 | 金属粒子担持触媒、触媒組成物、および、ヒドロキシ脂肪酸の製造方法 |
| CN105111044B (zh) * | 2015-08-17 | 2018-02-16 | 山东成泰化工有限公司 | 由丁烯醇合成异戊烯醇的方法 |
| CN106588550B (zh) * | 2015-10-14 | 2019-12-31 | 中国石油化工股份有限公司 | 一种提高2-甲基-2-丁烯含量的方法 |
| CN105541544A (zh) * | 2015-12-16 | 2016-05-04 | 绍兴明业化纤有限公司 | 一种3-甲基-3-丁烯-1-醇的生产方法 |
| US10414707B2 (en) | 2016-03-15 | 2019-09-17 | Basf Se | Process for producing prenol and prenal from isoprenol |
| CN109422633B (zh) * | 2017-08-28 | 2021-11-19 | 中国科学院大连化学物理研究所 | 一种金催化剂催化氧化异戊烯醇制异戊烯醛的方法 |
| CN109422632B (zh) * | 2017-08-28 | 2021-11-09 | 中国科学院大连化学物理研究所 | 一种催化氧化异戊烯醇制异戊烯醛的方法 |
| CN107812531B (zh) * | 2017-10-19 | 2020-06-16 | 万华化学集团股份有限公司 | 一种烯属不饱和醇制备烯属不饱和醛的催化剂、其制备方法及其用途 |
| CN107952459B (zh) * | 2017-12-07 | 2020-08-28 | 万华化学集团股份有限公司 | 大环烯酮的合成方法、及一种催化剂和它的应用 |
| CN110368937B (zh) * | 2019-08-09 | 2022-02-22 | 中触媒新材料股份有限公司 | 一种3-甲基-2-丁烯-1-醇合成异戊烯醛的方法 |
| EP4526283A1 (en) | 2022-05-20 | 2025-03-26 | Basf Se | Purification of an ethylenically unsaturated alcohol stream, preparation of an ethylenically unsaturated aldehyde, in particular prenal, and com- pounds derived therefrom |
| WO2024246272A1 (en) * | 2023-06-02 | 2024-12-05 | Basf Se | Processes for the preparation of citral and interrelated products |
| WO2025108976A2 (en) | 2023-11-20 | 2025-05-30 | Basf Se | Process for isomerizing an ethylenically unsaturated alcohol |
| WO2025114332A1 (en) | 2023-11-27 | 2025-06-05 | Basf Se | Process for isomerizing an ethylenically unsaturated alcohol in a cascade of reactors |
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-
2008
- 2008-02-28 DE DE102008011767A patent/DE102008011767B4/de active Active
-
2009
- 2009-02-27 EP EP09715609A patent/EP2257513B1/de active Active
- 2009-02-27 MX MX2010009123A patent/MX2010009123A/es not_active Application Discontinuation
- 2009-02-27 US US12/920,139 patent/US8410315B2/en active Active
- 2009-02-27 CA CA2715655A patent/CA2715655A1/en not_active Abandoned
- 2009-02-27 ES ES09715609T patent/ES2371324T3/es active Active
- 2009-02-27 CA CA2716267A patent/CA2716267A1/en not_active Abandoned
- 2009-02-27 AT AT09715609T patent/ATE520636T1/de active
- 2009-02-27 EP EP09715510.5A patent/EP2257514B1/de active Active
- 2009-02-27 WO PCT/EP2009/052383 patent/WO2009106621A1/de not_active Ceased
- 2009-02-27 WO PCT/EP2009/052384 patent/WO2009106622A1/de not_active Ceased
- 2009-02-27 JP JP2010548125A patent/JP5470277B2/ja active Active
- 2009-02-27 US US12/920,150 patent/US8263813B2/en active Active
- 2009-02-27 MX MX2010009196A patent/MX2010009196A/es not_active Application Discontinuation
- 2009-02-27 ES ES09715510.5T patent/ES2560112T3/es active Active
- 2009-02-27 CN CN200980106821.0A patent/CN101959837B/zh active Active
- 2009-02-27 CN CN200980106914.3A patent/CN101965325B/zh active Active
- 2009-02-27 JP JP2010548126A patent/JP5571003B2/ja active Active
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2012
- 2012-09-10 US US13/608,577 patent/US8563785B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2257513A1 (de) | 2010-12-08 |
| US20110004032A1 (en) | 2011-01-06 |
| WO2009106621A1 (de) | 2009-09-03 |
| US8563785B2 (en) | 2013-10-22 |
| US8410315B2 (en) | 2013-04-02 |
| ATE520636T1 (de) | 2011-09-15 |
| WO2009106621A8 (de) | 2010-09-16 |
| CA2715655A1 (en) | 2009-09-03 |
| EP2257514B1 (de) | 2015-10-28 |
| JP2011513283A (ja) | 2011-04-28 |
| JP5571003B2 (ja) | 2014-08-13 |
| US8263813B2 (en) | 2012-09-11 |
| DE102008011767B4 (de) | 2012-07-26 |
| CN101965325B (zh) | 2013-08-21 |
| CN101959837A (zh) | 2011-01-26 |
| EP2257514A1 (de) | 2010-12-08 |
| MX2010009196A (es) | 2010-09-10 |
| WO2009106622A1 (de) | 2009-09-03 |
| US20110004025A1 (en) | 2011-01-06 |
| US20130006021A1 (en) | 2013-01-03 |
| ES2371324T3 (es) | 2011-12-29 |
| CN101965325A (zh) | 2011-02-02 |
| EP2257513B1 (de) | 2011-08-17 |
| CN101959837B (zh) | 2014-05-21 |
| DE102008011767A1 (de) | 2009-09-10 |
| JP2011513284A (ja) | 2011-04-28 |
| JP5470277B2 (ja) | 2014-04-16 |
| MX2010009123A (es) | 2010-10-25 |
| CA2716267A1 (en) | 2009-09-03 |
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