ES2639830T3 - Catalizador y procedimiento para la hidroformilación de compuestos insaturados mediante catálisis SILP - Google Patents

Catalizador y procedimiento para la hidroformilación de compuestos insaturados mediante catálisis SILP Download PDF

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ES2639830T3
ES2639830T3 ES14750354.4T ES14750354T ES2639830T3 ES 2639830 T3 ES2639830 T3 ES 2639830T3 ES 14750354 T ES14750354 T ES 14750354T ES 2639830 T3 ES2639830 T3 ES 2639830T3
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hydroformylation
catalyst
procedure
unsaturated compounds
composition
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Katrin Marie DYBALLA
Robert Franke
Hanna HAHN
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Evonik Operations GmbH
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Evonik Degussa GmbH
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    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0209—Esters of carboxylic or carbonic acids
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
    • B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
    • 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
    • B01J31/1616—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts
    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • 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
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-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
    • 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
    • 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
    • B01J2531/822—Rhodium
    • 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
    • B01J31/40—Regeneration or reactivation
    • B01J31/4015—Regeneration or reactivation of catalysts containing metals
    • B01J31/4092—Regeneration or reactivation of catalysts containing metals involving a stripping step, with stripping gas or solvent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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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)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Composición que comprende: a) al menos un material soporte, que es preferentemente poroso; b) al menos un líquido iónico; c) al menos un metal, seleccionado a partir del 9º grupo del sistema periódico de los elementos; d) al menos un compuesto de la fórmula (II): **(Ver fórmula)** e) opcionalmente una o varias aminas orgánicas.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
5 con R = C6-a C20-alquilo
En la composición según la invención, el metal se selecciona preferentemente entre:
cobalto, rodio, iridio, en especial rodio.
La composición según la invención se puede producir de modo conocido mediante mezclado de los componentes. La composición según la invención se produce mediante el procedimiento descrito a continuación, o bien es
10 obtenible a partir del mismo.
El procedimiento según la invención para la producción de la composición según la invención se distingue por que presenta los pasos:
A) disposición de un precursor de al menos un compuesto de un metal del 9º grupo del sistema periódico de los elementos, ventajosamente rodio; 15 B) puesta en contacto de al menos un compuesto de un metal del 9º grupo del sistema periódico de los elementos, ventajosamente rodio, con un exceso molar de al menos un compuesto de la fórmula (II):
imagen9
pudiendo presentar el compuesto de la fórmula (II) otros componentes, que se pueden atribuir a impurezas en la
20 síntesis de (II), como por ejemplo eductos, productos de hidrólisis, oxidación no transformados de (II) u otras impurezas; al menos un líquido iónico, pudiéndose emplear preferentemente como líquido iónicos aquellos en los que el anión se selecciona a partir del grupo que comprende:
tetrafluorborato ([BF4]-), hexafluorfosfato ([PF6]-), dicianamida ([N(CN)2]-), bis(trifluormetilsulfonil)imida ([NTf2]-), tricianometida ([C(CN)3]-), tetracianoborato ([B(CN)4]-), halogenuros (Cl-, Br-, F-, I-), hexafluorantimoniato ([SbF6]-), 25 hexafluorarseniato ([AsF6]-), sulfato ([SO4]2-), tosilato ([C7H7SO3]-), triflato (CF3SO3-), nonaflato ([C4F9SO3-), tris
9
imagen10
imagen11
imagen12
imagen13
imagen14
imagen15
imagen16
imagen17
Tabla 1:
imagen18
Composición mezcla C4 2º ejemplo comparativo / %[a] Rh-(VIII) Composición mezcla C4 ejemplo según la invención / %[a] Rh-(II)
1-Buteno + isobuteno
27,6 (27,5+< 0,1) 27,4 (27,3+< 0,1)
Cis-2-buteno
16 15
Trans-2-buteno
28 25
n-butano
28,3 29,5
Iso-butano
< 0,1 < 0,1
2-metilbutano
imagen19 3
[a] Superficie por GC en % (columna firma Agilent Technologies longitud 50 m, diámetro interno 0,32 mm, grosor de película 0,5 µm, gas soporte helio; detector: FID, temperatura de evaporación 473,15 K, proporción de división 33,5:1, flujo de columna constante de helio 91,6 ml min-1 , temperatura de detector 523,15 K, gradiente de calefacción: temperatura inicial 323,15 K, tiempo de retención 15 minutos, calefacción a 473,15 K con 25 K min-1 , tiempo de retención 40 min, tiempo total por medida 61 min)
1er Ejemplo comparativo según el documento DE 10 2013217174:
En la figura 1 se muestra un experimento de catálisis para la hidroformilación de mezclas C4 (composición, vése tabla 2). Tabla 2:
imagen20
Composición mezcla C4 A 1er ejemplo comparativo / %[a] Rh-(II): 0 -2615 h Composición mezcla C4 B 1er ejemplo comparativo / %[a] Rh-(II): 2615 -3506 h
1-Buteno + isobuteno
24,9 (24,8 + < 0,1) 27 (26,9+< 0,1)
Cis-2-buteno
16 16
Trans-2-buteno
33 29
n-butano
26 27,9
Iso-butano
< 0,1 < 0,1
[a] Superficie por GC en % (columna firma Agilent Technologies longitud 50 m, diámetro interno 0,32 mm, grosor de película 0,5 µm, gas soporte helio; detector: FID, temperatura de evaporación 473,15 K, proporción de división 33,5:1, flujo de columna constante de helio 91,6 ml min-1 , temperatura de detector 523,15 K, gradiente de
18
imagen21
imagen22

Claims (1)

  1. imagen1
    imagen2
    imagen3
    imagen4
    imagen5
    imagen6
ES14750354.4T 2013-08-28 2014-08-08 Catalizador y procedimiento para la hidroformilación de compuestos insaturados mediante catálisis SILP Active ES2639830T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE102013217166 2013-08-28
DE102013217166.8A DE102013217166A1 (de) 2013-08-28 2013-08-28 Verfahren zur Hydroformylierung von ungesättigten Verbindungen durch SILP-Katalyse
PCT/EP2014/067072 WO2015028284A1 (de) 2013-08-28 2014-08-08 Katalysator und verfahren zur hydroformylierung von ungesättigten verbindungen durch silp-katalyse

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ES2639830T3 true ES2639830T3 (es) 2017-10-30

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DE (1) DE102013217166A1 (es)
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DE102013217174A1 (de) 2013-08-28 2015-03-05 Evonik Industries Ag Zusammensetzung und deren Verwendung in Verfahren zur Hydroformylierung von ungesättigten Verbindungen
EP3632889B1 (de) 2018-10-05 2022-11-02 Evonik Operations GmbH Verfahren zur hydroformylierung von c2- bis c5-olefinen ohne zwischengeschaltete stofftrennung
ES2976199T3 (es) 2018-10-05 2024-07-26 Evonik Oxeno Gmbh & Co Kg Procedimiento para la hidroformilación de olefinas de cadena corta en la corriente de reciclaje de una hidroformilación en fase líquida
US10647650B2 (en) * 2018-10-05 2020-05-12 Evonik Operations Gmbh Process for hydroformylating short-chain olefins using a heterogenized catalyst system without ionic liquid
WO2020070052A1 (de) 2018-10-05 2020-04-09 Evonik Operations Gmbh Verfahren zur hydroformylierung von kurzkettigen olefinen in der gasphase
EP3632888B1 (de) 2018-10-05 2021-04-14 Evonik Operations GmbH Verfahren zur in-situ herstellung eines hydroformylierungskatalysatorsystems, welches heterogenisiert auf einem support vorliegt
ES2969859T3 (es) 2018-10-05 2024-05-23 Evonik Oxeno Gmbh & Co Kg Procedimiento para la hidroformilación de olefinas de cadena corta en corrientes de gas de escape ricas en alcanos
US10654784B2 (en) * 2018-10-05 2020-05-19 Evonik Operations Gmbh Process for hydroformylating short-chain olefins in the gas phase
CN112679327B (zh) * 2021-01-12 2022-01-04 四川大学 一种烯烃两相氢甲酰化制备醛类化合物的方法
EP4091712B1 (de) 2021-05-18 2024-05-15 Evonik Oxeno GmbH & Co. KG Verfahren zur regenerierung eines katalysators für die hydroformylierung von olefinen in der gasphase
WO2024017514A1 (de) 2022-07-19 2024-01-25 Evonik Oxeno Gmbh & Co. Kg Verfahren zur hydroformylierung von kurzkettigen olefinen in der gasphase
WO2024017513A1 (de) 2022-07-19 2024-01-25 Evonik Oxeno Gmbh & Co. Kg Verfahren zur hydroformylierung von kurzkettigen olefinen in der gasphase
EP4389731A1 (de) 2022-12-19 2024-06-26 Evonik Oxeno GmbH & Co. KG Verfahren zur aktivitätserhaltung bei der abstellung der hydroformylierung

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EP3038752A1 (de) 2016-07-06
WO2015028284A1 (de) 2015-03-05
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