MX374198B - Método para preparar ésteres di- o tri-carboxílicos mediante alcoxicarbonilación de dienos que tienen dobles enlaces conjugados. - Google Patents
Método para preparar ésteres di- o tri-carboxílicos mediante alcoxicarbonilación de dienos que tienen dobles enlaces conjugados.Info
- Publication number
- MX374198B MX374198B MX2017009229A MX2017009229A MX374198B MX 374198 B MX374198 B MX 374198B MX 2017009229 A MX2017009229 A MX 2017009229A MX 2017009229 A MX2017009229 A MX 2017009229A MX 374198 B MX374198 B MX 374198B
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- cycloalkyl
- aryl
- palladium
- heteroaryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 12
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 abstract 9
- 125000006707 (C3-C12) heterocycloalkyl group Chemical group 0.000 abstract 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 abstract 1
- 239000012018 catalyst precursor Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 abstract 1
- 150000001875 compounds Chemical class 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
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 abstract 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 abstract 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 abstract 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 abstract 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 abstract 1
- HNNUTDROYPGBMR-UHFFFAOYSA-L palladium(ii) iodide Chemical compound [Pd+2].[I-].[I-] HNNUTDROYPGBMR-UHFFFAOYSA-L 0.000 abstract 1
- 239000011541 reaction mixture 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
-
- 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
- B01J31/2495—Ligands comprising a phosphine-P atom and one or more further complexing phosphorus atoms covered by groups B01J31/1845 - B01J31/1885, e.g. phosphine/phosphinate or phospholyl/phosphonate 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
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/44—Adipic acid esters
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/349—1,2- or 1,4-additions in combination with further or prior reactions by the same catalyst, i.e. tandem or domino reactions, e.g. hydrogenation or further addition reactions
-
- 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)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Abstract
La invención se refiere a un método que comprende los pasos de: a) cargar inicialmente un dieno que tiene dobles enlaces conjugados; b) adicionar un ligando de fosfina y un precursor de catalizador seleccionado a partir de dicloruro de paladio, dibromuro de paladio, diyoduro de paladio, acetilacetonato de paladio (II), acetato de paladio (II), bis(dibencilidenoacetona)paladio, bis(acetonitrilo)- dicloropaladio(II), (cinnamilo)dicloruro de paladio; c) adicionar un alcohol; d) alimentar en CO; d) calentar la mezcla de reacción, con conversión del dieno a un éster di- o tri-carboxílico; en donde el ligando de fosfina es un compuesto de acuerdo a la fórmula (I) ver formula(I), donde R1, R2, R3, R4 se seleccionan de -(C1-C12)-alquilo, - (C6-C20)-arilo, -(C3-C12)-cicloalquilo, -(C3-C12)- heterocicloalquilo, -(C3-C20)-heteroarilo; R5, R6 se seleccionan de -H, -(C1-C12)-alquilo, -(C6- C20)-arilo, -(C3-C12)-cicloalquilo, -(C3-C12)- heterocicloalquilo, -(C3-C20)-heteroarilo; y R1, R2, R3, R4, R5, R6, en el caso que estos sean - (C1-C12)-alquilo, -(C6-C20)-arilo, -(C3-C12)-cicloalquilo, -(C3- C12)-heterocicloalquilo o -(C3-C20)-heteroarilo, puede estar cada uno substituido independientemente entre sí por uno o más sustituyentes seleccionado 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 |
|---|---|---|---|
| EP16180048.7A EP3272731B1 (de) | 2016-07-19 | 2016-07-19 | Verfahren zur herstellung von di- oder tricarbonsäureestern durch alkoxycarbonylierung von dienen mit konjugierten doppelbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MX2017009229A MX2017009229A (es) | 2018-11-09 |
| MX374198B true MX374198B (es) | 2025-03-05 |
Family
ID=56550712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2017009229A MX374198B (es) | 2016-07-19 | 2017-07-13 | Método para preparar ésteres di- o tri-carboxílicos mediante alcoxicarbonilación de dienos que tienen dobles enlaces conjugados. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9981903B2 (es) |
| EP (1) | EP3272731B1 (es) |
| JP (1) | JP6434092B2 (es) |
| KR (1) | KR101960175B1 (es) |
| CN (1) | CN107628953B (es) |
| AR (1) | AR109094A1 (es) |
| BR (1) | BR102017015218B1 (es) |
| CA (1) | CA2974088C (es) |
| ES (1) | ES2734383T3 (es) |
| MX (1) | MX374198B (es) |
| MY (1) | MY179702A (es) |
| SG (1) | SG10201705860PA (es) |
| TW (1) | TWI679192B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112480170B (zh) * | 2020-12-02 | 2023-03-14 | 中国海洋石油集团有限公司 | 一种双膦化合物、包含其的催化剂体系及其应用 |
| CN116178127A (zh) * | 2021-11-26 | 2023-05-30 | 中国科学院大连化学物理研究所 | 一种烯烃和水或酸性水溶液制羧酸化合物反应的方法 |
| ES2992252T3 (es) * | 2021-12-17 | 2024-12-11 | Evonik Oxeno Gmbh & Co Kg | Procedimiento para la hidroformilación de olefinas empleando Pt y DPEfos |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792620A (en) * | 1983-10-14 | 1988-12-20 | Bp Chemicals Limited | Carbonylation catalysts |
| TW524801B (en) * | 1999-03-22 | 2003-03-21 | Shell Int Research | Process for the carbonylation of conjugated dienes |
| US20060235241A1 (en) * | 2003-05-22 | 2006-10-19 | Eit Drent | Process for the carbonylation of a conuugated diene |
| WO2006084889A1 (en) * | 2005-02-11 | 2006-08-17 | Shell Internationale Research Maatschappij B.V. | Process for the preparation of a dicarboxylic acid |
| 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 |
| US9376365B2 (en) * | 2012-11-23 | 2016-06-28 | Firmenich Sa | Hydrocarbonylation or methoxycarbonylation of 1,3-diene derivatives with palladium complex |
| ES2711749T3 (es) | 2015-07-23 | 2019-05-07 | Evonik Degussa Gmbh | Ligando de fosfina y catalizadores de paladio basados en el mismo para la alcoxicarbonilación de compuestos etilénicamente insaturados |
-
2016
- 2016-07-19 ES ES16180048T patent/ES2734383T3/es active Active
- 2016-07-19 EP EP16180048.7A patent/EP3272731B1/de active Active
-
2017
- 2017-07-13 MX MX2017009229A patent/MX374198B/es active IP Right Grant
- 2017-07-14 BR BR102017015218-9A patent/BR102017015218B1/pt active IP Right Grant
- 2017-07-14 JP JP2017137960A patent/JP6434092B2/ja active Active
- 2017-07-17 SG SG10201705860PA patent/SG10201705860PA/en unknown
- 2017-07-17 US US15/651,105 patent/US9981903B2/en active Active
- 2017-07-17 MY MYPI2017702623A patent/MY179702A/en unknown
- 2017-07-17 TW TW106123839A patent/TWI679192B/zh active
- 2017-07-18 KR KR1020170090736A patent/KR101960175B1/ko active Active
- 2017-07-18 CA CA2974088A patent/CA2974088C/en active Active
- 2017-07-18 CN CN201710585530.0A patent/CN107628953B/zh active Active
- 2017-07-19 AR ARP170102011A patent/AR109094A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TW201815742A (zh) | 2018-05-01 |
| CN107628953A (zh) | 2018-01-26 |
| JP2018039783A (ja) | 2018-03-15 |
| MY179702A (en) | 2020-11-11 |
| ES2734383T3 (es) | 2019-12-05 |
| EP3272731A1 (de) | 2018-01-24 |
| US20180022687A1 (en) | 2018-01-25 |
| CN107628953B (zh) | 2020-08-11 |
| US9981903B2 (en) | 2018-05-29 |
| SG10201705860PA (en) | 2018-02-27 |
| KR20180009716A (ko) | 2018-01-29 |
| JP6434092B2 (ja) | 2018-12-05 |
| KR101960175B1 (ko) | 2019-03-19 |
| TWI679192B (zh) | 2019-12-11 |
| BR102017015218A2 (pt) | 2018-02-06 |
| CA2974088C (en) | 2022-06-21 |
| MX2017009229A (es) | 2018-11-09 |
| BR102017015218B1 (pt) | 2022-01-25 |
| EP3272731B1 (de) | 2019-05-01 |
| AR109094A1 (es) | 2018-10-31 |
| CA2974088A1 (en) | 2018-01-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX377077B (es) | Proceso para la alcoxicarbonilación de compuestos insaturados etilénicamente con ligandos de monofosfina | |
| MX2016009397A (es) | Compuestos basados en ferroceno y catalizadores de paladio basados en los mismos para la alcoxicarbonilacion de compuestos etilenicamente insaturados. | |
| MX374198B (es) | Método para preparar ésteres di- o tri-carboxílicos mediante alcoxicarbonilación de dienos que tienen dobles enlaces conjugados. | |
| MX376073B (es) | Metodos para controlar emisiones de oxido nitroso. | |
| MX2016007993A (es) | Catalizador de oxidación diésel que contiene manganeso. | |
| PH12013500954A1 (en) | Drug derivatives | |
| RU2014133060A (ru) | Курительное изделие | |
| ATE481373T1 (de) | 1,4-hydrierung von sorbol mit ru-komplexen | |
| MX2018013563A (es) | Ligandos p-quirales de fosfina y su uso para sintesis asimetrica. | |
| WO2014182670A3 (en) | Selective 1,2-hydrosilylation of terminally unsaturated 1,3-dienes using iron catalysts | |
| EP4122924A3 (en) | Compounds and the use thereof in metathesis reactions | |
| WO2007141662A3 (en) | Amidine-carboxylic acid complex, bridged polynuclear complex derived therefrom, production methods therefor, and use for preparing supported metal or metal oxide clusters | |
| MY167613A (en) | Mathod of manufacturing magnetic recording medium and magnetic recording medium | |
| WO2014200677A3 (en) | System and method for control of fuel injector spray | |
| WO2018162208A3 (en) | Particles for fluidised bed reaction methods and fluidised bed reaction methods | |
| EA201591040A1 (ru) | Способ окислительного дегидрирования н-бутенов в бутадиен | |
| MY164142A (en) | Multiple burn zones with independent circulation loops | |
| MX2017009228A (es) | Proceso para la alcoxicarbonilación de alcoholes. | |
| JP2019527805A5 (es) | ||
| JP2015027934A5 (es) | ||
| WO2012167198A3 (en) | Dirhodium catalyst compositions and synthetic processes related thereto | |
| MX2017009234A (es) | Proceso para la preparación de ésteres por medio de carbonilación de éteres. | |
| UY38264A (es) | N- (tetrazol-5-il)- y carboxamidas de n- (1,3,4-oxadiazol-2-il) arilo | |
| WO2014202792A3 (en) | Oxidation dyeing process using a composition comprising an aminobenzimidazolone oxidation base and a metal catalyst | |
| MX2015010916A (es) | Hidrogenacion selectiva de aldehidos con complejos de ligandos ru/bidentados. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HC | Change of company name or juridical status |
Owner name: DE-STA-CO EUROPE GMBH.* |
|
| FG | Grant or registration |