ES2722052T3 - Procedimiento para la alcoxicarbonilación de olefinas en un medio con baja concentración de ácidos de Brønsted - Google Patents
Procedimiento para la alcoxicarbonilación de olefinas en un medio con baja concentración de ácidos de Brønsted Download PDFInfo
- Publication number
- ES2722052T3 ES2722052T3 ES16180058T ES16180058T ES2722052T3 ES 2722052 T3 ES2722052 T3 ES 2722052T3 ES 16180058 T ES16180058 T ES 16180058T ES 16180058 T ES16180058 T ES 16180058T ES 2722052 T3 ES2722052 T3 ES 2722052T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- cycloalkyl
- heteroaryl
- aryl
- compound
- 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.)
- Active
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000001336 alkenes Chemical class 0.000 title 1
- 238000007083 alkoxycarbonylation reaction Methods 0.000 title 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000003446 ligand Substances 0.000 abstract 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 4
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000004437 phosphorous atom Chemical group 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
- C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
- B01J27/13—Platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Procedimiento a) disposición de un compuesto con insaturación etilénica; b) adición de un complejo ligando-metal que comprende Pd y un ligando fosfina bidentado, o adición de un ligando fosfina bidentado, que comprende Pd; c) adición de un alcohol; d) alimentación de CO; e) calentamiento de la mezcla de reacción, haciéndose reaccionar el compuesto con insaturación etilénica para dar un éster, añadiéndose a la mezcla de reacción menos de un 0,1 % en moles, referido a la cantidad de sustancia del compuesto con insaturación etilénica, de ácidos de Brønsted con una fortaleza de ácido de pKs <= 3, caracterizado por que el ligando fosfina está sustituido con al menos un resto heteroarilo en al menos un átomo de fósforo; seleccionándose el ligando fosfina bidentado a partir de un compuesto según una de las (I) y (II) **(Ver fórmulas)** seleccionándose R1, R2, R3, R4, R1', R2', R3', R4', independientemente entre sí en cada caso, a partir de -(C1-C12)- alquilo, -(C3-C12)-cicloalquilo, -(C3-C12)-heterocicloalquilo, -(C6-C20)-arilo, -(C3-C20)-heteroarilo; representando al menos uno de los restos R1, R2, R3, R4, o bien al menos uno de los restos R1', R2', R3', R4' un resto - (C3-C20)-heteroarilo; y estando sustituidos R1, R2, R3, R4, R1', R2', R3', R4', si éstos representan -(C1-C12)-alquilo, -(C3-C12)-cicloalquilo, -(C3- C12)-heterocicloalquilo, -(C6-C20)-arilo, o -(C3-C20)-heteroarilo, independientemente entre sí en cada caso, con uno o varios sustituyentes seleccionados a partir de -(C1-C12)- alquilo, -(C3-C12)-cicloalquilo, -(C3-C12)-heterocicloalquilo, -O-(C1-C12)-alquilo, -O-(C1-C12)-alquil-(C6-C20)-arilo, -O-(C3- C12)-cicloalquilo, -S-(C1-C12)-alquilo, -S-(C3-C12)-cicloalquilo,-COO-(C1-C12)-alquilo, -COO-(C3-C12)-cicloalquilo, - CONH-(C1-C12)-alquilo, -CONH-(C3-C12)-cicloalquilo, -CO-(C1-C12)-alquilo, -CO-(C3-C12)-cicloalquilo, -N-[(C1-C12)- alquilo]2, -(C6-C20)-arilo, -(C6-C20)-aril-(C1-C12)-alquilo, -(C6-C20)-aril-O-(C1-C12)-alquilo, -(C3-C20)-heteroarilo, -(C3- C20)-heteroaril-(C1-C12)-alquilo, -(C3-C20)-heteroaril-O-(C1-C12)-alquilo, -COOH, -OH, -SO3H, -NH2, halógeno.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16180058.6A EP3272733B1 (de) | 2016-07-19 | 2016-07-19 | Verfahren zur alkoxycarbonylierung von olefinen in einem medium mit geringer brønstedsäurenkonzentration |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2722052T3 true ES2722052T3 (es) | 2019-08-07 |
Family
ID=56497603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES16180058T Active ES2722052T3 (es) | 2016-07-19 | 2016-07-19 | Procedimiento para la alcoxicarbonilación de olefinas en un medio con baja concentración de ácidos de Brønsted |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10562838B2 (es) |
| EP (1) | EP3272733B1 (es) |
| JP (1) | JP6571135B2 (es) |
| KR (1) | KR102039377B1 (es) |
| CN (1) | CN107628952A (es) |
| CA (1) | CA2973694C (es) |
| ES (1) | ES2722052T3 (es) |
| MX (1) | MX377075B (es) |
| MY (1) | MY175178A (es) |
| SG (1) | SG10201705858UA (es) |
| TW (1) | TWI691482B (es) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2787299T3 (es) | 2017-12-21 | 2020-10-15 | Evonik Degussa Gmbh | Proceso para la conversión directa de alquenos en ácidos carboxílicos |
| US11440863B2 (en) * | 2019-06-12 | 2022-09-13 | Evonik Operations Gmbh | Process for preparing an alcohol from hydrocarbons |
| PL3842411T3 (pl) * | 2019-12-17 | 2023-10-02 | Evonik Operations Gmbh | Ester trimetylowy kwasu 3,3',3''-(cykloheksano-1,2,4-triylo)tripropionowego |
| EP4001256A1 (de) * | 2020-11-24 | 2022-05-25 | Evonik Operations GmbH | Verfahren zur alkoxycarbonylierung von ethylenisch ungesättigter verbindungen unter einsatz von benzolbasierte diphosphinliganden und aluminiumtriflat |
| CN115772195A (zh) * | 2021-09-06 | 2023-03-10 | 惠州凯特立斯科技有限公司 | 基于吡啶的膦配体化合物及其应用 |
| CN116003467A (zh) * | 2021-10-21 | 2023-04-25 | 惠州凯特立斯科技有限公司 | 一种新型三膦化合物及其合成方法与应用 |
| JP7474310B2 (ja) * | 2021-12-17 | 2024-04-24 | エボニック オクセノ ゲーエムベーハー ウント コー． カーゲー | Ｐｔとキサントフォスを用いるオレフィンのヒドロホルミル化方法 |
| WO2023117754A1 (de) | 2021-12-23 | 2023-06-29 | Röhm Gmbh | Verfahren zur herstellung von alkylmethacrylaten mit verbesserter ausbeute und verminderten emissionen flüchtiger organischer verbindungen |
| CN115819461B (zh) * | 2022-11-02 | 2024-06-07 | 黄河三角洲京博化工研究院有限公司 | 一种双齿膦配体及其制备方法 |
| WO2025237424A1 (zh) * | 2024-05-17 | 2025-11-20 | 中国科学院上海有机化学研究所 | 一种长碳烯烃氢酯化合成长碳脂肪酸酯的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2034971A1 (en) * | 1990-02-05 | 1991-08-06 | Eit Drent | Carbonylation catalyst system |
| BE1007422A3 (nl) | 1993-08-23 | 1995-06-13 | Dsm Nv | Werkwijze voor de bereiding van een mengsel van penteenzure alkylesters. |
| GB9717059D0 (en) | 1997-08-13 | 1997-10-15 | Ici Plc | Method of manufacturing phosphine compound |
| EP0967015B1 (de) * | 1998-06-19 | 2005-01-12 | Degussa AG | Verwendung von Ferrocenylliganden zur katalytischen enantioselektiven Hydrierung |
| GB201000078D0 (en) * | 2010-01-05 | 2010-02-17 | Lucite Int Uk Ltd | Process for the carbonylation of ethylenically unsaturated compounds, novel carbonylation ligands and catalyst systems incorporatng such ligands |
| EP3121179B1 (de) | 2015-07-23 | 2018-10-17 | Evonik Degussa GmbH | Ferrocenbasierte verbindungen und darauf basierende palladium-katalysatoren für die alkoxycarbonylierung ethylenisch ungesättigter verbindungen |
-
2016
- 2016-07-19 EP EP16180058.6A patent/EP3272733B1/de active Active
- 2016-07-19 ES ES16180058T patent/ES2722052T3/es active Active
-
2017
- 2017-07-13 MX MX2017009235A patent/MX377075B/es active IP Right Grant
- 2017-07-14 MY MYPI2017702587A patent/MY175178A/en unknown
- 2017-07-14 CA CA2973694A patent/CA2973694C/en active Active
- 2017-07-14 JP JP2017137958A patent/JP6571135B2/ja active Active
- 2017-07-17 SG SG10201705858UA patent/SG10201705858UA/en unknown
- 2017-07-17 US US15/651,042 patent/US10562838B2/en active Active
- 2017-07-17 TW TW106123834A patent/TWI691482B/zh active
- 2017-07-18 KR KR1020170090732A patent/KR102039377B1/ko active Active
- 2017-07-18 CN CN201710585090.9A patent/CN107628952A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| MX2017009235A (es) | 2018-09-10 |
| CA2973694C (en) | 2022-09-27 |
| EP3272733A1 (de) | 2018-01-24 |
| MX377075B (es) | 2025-03-07 |
| KR102039377B1 (ko) | 2019-11-04 |
| US20180022686A1 (en) | 2018-01-25 |
| US10562838B2 (en) | 2020-02-18 |
| SG10201705858UA (en) | 2018-02-27 |
| TWI691482B (zh) | 2020-04-21 |
| TW201815741A (zh) | 2018-05-01 |
| KR20180009714A (ko) | 2018-01-29 |
| JP2018058818A (ja) | 2018-04-12 |
| JP6571135B2 (ja) | 2019-09-04 |
| CA2973694A1 (en) | 2018-01-19 |
| MY175178A (en) | 2020-06-12 |
| EP3272733B1 (de) | 2019-01-02 |
| CN107628952A (zh) | 2018-01-26 |
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