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 PDF

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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
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alkyl
cycloalkyl
heteroaryl
aryl
compound
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ES16180058T
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English (en)
Inventor
Xiangjie Fang
Kaiwu Dong
Helfreid Neumann
Ralf Jackstell
Matthias Beller
Dirk Fridag
Dieter Hess
Katrin Marie Dyballa
Frank Geilen
Robert Franke
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Evonik Operations GmbH
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Evonik Degussa GmbH
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    • 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

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  • 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.
ES16180058T 2016-07-19 2016-07-19 Procedimiento para la alcoxicarbonilación de olefinas en un medio con baja concentración de ácidos de Brønsted Active ES2722052T3 (es)

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

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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) MX2017009235A (es)
MY (1) MY175178A (es)
SG (1) SG10201705858UA (es)
TW (1) TWI691482B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3502085B1 (de) 2017-12-21 2020-03-11 Evonik Operations GmbH Verfahren zur direkten umsetzung von alkenen zu carbonsäuren
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
WO2023117754A1 (de) 2021-12-23 2023-06-29 Röhm Gmbh Verfahren zur herstellung von alkylmethacrylaten mit verbesserter ausbeute und verminderten emissionen flüchtiger organischer verbindungen

Family Cites Families (6)

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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
MY172677A (en) 2015-07-23 2019-12-10 Evonik Operations Gmbh Benzene-based diphosphine ligands for alkoxycarbonylation

Also Published As

Publication number Publication date
TWI691482B (zh) 2020-04-21
JP6571135B2 (ja) 2019-09-04
US20180022686A1 (en) 2018-01-25
CA2973694A1 (en) 2018-01-19
CN107628952A (zh) 2018-01-26
JP2018058818A (ja) 2018-04-12
TW201815741A (zh) 2018-05-01
SG10201705858UA (en) 2018-02-27
KR102039377B1 (ko) 2019-11-04
KR20180009714A (ko) 2018-01-29
EP3272733A1 (de) 2018-01-24
EP3272733B1 (de) 2019-01-02
MX2017009235A (es) 2018-09-10
US10562838B2 (en) 2020-02-18
MY175178A (en) 2020-06-12
CA2973694C (en) 2022-09-27

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