ES2527520T3 - Síntesis de carbonatos cíclicos - Google Patents

Síntesis de carbonatos cíclicos Download PDF

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ES2527520T3
ES2527520T3 ES09717420.5T ES09717420T ES2527520T3 ES 2527520 T3 ES2527520 T3 ES 2527520T3 ES 09717420 T ES09717420 T ES 09717420T ES 2527520 T3 ES2527520 T3 ES 2527520T3
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Michael North
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University of York
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University of York
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C07D317/38—Ethylene carbonate
    • 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
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
    • B01J21/08—Silica
    • 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
    • B01J31/0239—Quaternary ammonium 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
    • 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
    • B01J31/1625—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups
    • B01J31/1633—Coordination complexes, e.g. organometallic complexes, immobilised on an inorganic support, e.g. ship-in-a-bottle type catalysts immobilised by covalent linkages, i.e. pendant complexes with optional linking groups covalent linkages via silicon containing groups
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D317/34—Oxygen atoms
    • C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/069—Aluminium compounds without C-aluminium linkages
    • 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
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0213—Complexes without C-metal linkages
    • B01J2531/0216—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
    • 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
    • B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
    • B01J2531/31—Aluminium
    • 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
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/40—Non-coordinating groups comprising nitrogen
    • B01J2540/42—Quaternary ammonium groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/11—Compounds covalently bound to a solid support

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

Un catalizador de aluminio(salen) dimérico de fórmula I:**Fórmula** en el que: Y-Q es CRC1>=N o CRC1RC2-NRN1, donde RC1, RC2 y RN1 se seleccionan independientemente entre H, halo, C1-20 alquilo opcionalmente sustituido, C5-20 arilo opcionalmente sustituido, éter y nitro; cada uno de los sustituyentes R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 y R16, se selecciona independientemente entre H, halo, alquilo C1-20 opcionalmente sustituido, arilo C5-20 opcionalmente sustituido, heterociclilo C3-20 opcionalmente sustituido, éter y nitro; X1 y X2 son independientemente o bien (i) una cadena de alquileno C2-5, que está opcionalmente sustituida con uno o más grupos seleccionados entre alquilo C1-4 y arilo C5-7, o una cadena de bisoxialquileno C1-3, que está opcionalmente sustituida con uno o más grupos seleccionados entre alquilo C1-4 y arilo C5-7 o (ii) representa un grupo divalente seleccionado entre arileno C5-7, alquileno cíclico C5-7 y heterociclileno C3-7, que pueden estar opcionalmente sustituidos; (i) (a) al menos uno de R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 y R16 se selecciona entre LA, donde L es un enlace sencillo o un grupo alquileno C1-10 y A es un grupo amonio emparejado con un contraión seleccionado entre Cl, Br y I; y/o (b) al menos uno de X1 y X2 es un grupo heterocicleno C3-7 divalente, que contiene un átomo del anillo que es un átomo de nitrógeno cuaternario emparejado con un contraión seleccionado entre Cl, Br y I; y/o (c) al menos uno de X1 y X2 es una cadena de alquileno C2-5 o una cadena de bisoxialquileno C1-3, sustituido con un grupo -Q-L-A, donde Q es o bien -C(>=O)-O-, -C(>=O)-NH- o un enlace sencillo; y/o (ii) (a) uno de R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 y R16 es L-A', donde L es como se ha definido anteriormente y A' es un grupo enlazador de amonio unido a un soporte sólido y emparejado con un contraión seleccionado entre Cl, Br y I; o (b) uno de X1 y X2 es un grupo heterocicleno C3-7 divalente, que contiene un átomo del anillo que es un nitrógeno cuaternario que forma parte de un grupo enlazador de amonio unido a un soporte sólido y emparejado con un contraión seleccionado entre Cl, Br y I; o (c) uno de X1 y X2 es una cadena de alquileno C2-5 o una cadena de bisoxialquileno C1-3, sustituidas con un grupo -Q-L-A'.

Description

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E09717420
08-01-2015
(c) Se usó el procedimiento anterior pero con el catalizador (35) y dio un resultado de conversión del 81 % de óxido de etileno a carbonato de etileno después de un tiempo de reacción de 24 horas.
Ejemplo 16: Uso de catalizadores inmovilizados para convertir óxido de etileno en carbonato de etileno en 5 condiciones de flujo continuo
Se ilustra en la Figura 1 el reactor de flujo. Se recogió óxido de etileno a partir de una bombona suministrada comercialmente, como un líquido en un vaso enfriado a -78 ºC y se colocó, con una barra agitadora magnética, dentro de un recipiente de presión de acero inoxidable de 360 ml preenfriado (-10 a -40 ºC) (3). Después se selló el 10 recipiente. Se suministraron gases de nitrógeno y dióxido de carbono a partir de bombonas a través de unidades controladoras de flujo (1) y sus líneas respectivas se fusionaron a la entrada del recipiente de presión (véase diagrama). Todas las tuberías usadas en el sistema estaban compuestas de acero inoxidable con un diámetro interno de aproximadamente 1,6 mm. Se controló la temperatura del recipiente a presión (3) mediante un baño enfriado criostáticamente (2) para proporcionar la velocidad de evaporación requerida de óxido de etileno a un 15 caudal particular de N2 y CO2. Esto se determinó haciendo pasar la línea de salida del recipiente directamente a un sistema GC (6) equipado con una columna capaz de separar los tres gases. Después, se conectó la línea de salida del recipiente a un reactor tubular de acero inoxidable (4) (15 cm x 10 mm) cargado con un catalizador soportado sólido y con un tapón de algodón de pequeño volumen en ambos extremos. El reactor tubular (4) se mantuvo o bien a temperatura ambiente o inmerso en un baño termostático de agua. La mezcla de CO2, óxido de etileno y N2 se
20 hizo pasar a través de la columna del reactor a un caudal constante. Se conectó la salida del reactor (4) a un vial de vidrio sellado (5) a través de una aguja para recoger cualquier producto no gaseoso. La salida desde el receptáculo de producto pasó a un sistema GC (6) que se usó para determinar las concentraciones de CO2, N2 y óxido de etileno en la corriente de gas efluente. El resultado obtenido con ambos catalizadores soportados de sílice y poliestireno se dan en la siguiente tabla.
25
Ensayo
Catalizador (cantidad g) Flujo de N2 (ml/min) Flujo de CO2 (ml/min) Temperatura (ºC) delrecipiente a presión Consumo óxido de etileno(ml/h) Tiempo (h) Temperatura del reactor (°C) Rendimiento carbonato deetileno
1
29 (2,51) 25 25 -40 1,0 19 ambiente 0,14 g, 0,15 %
2
35 (1,95) 25 25 -40 1,0 19 ambiente 0,08 g, 0,1 %
3
35 (1,17) 2,5 2,5 -10 0,21 120 ambiente 1,1 g, 1,5 %
4
35 (1,17) 2,5 1,0 -10 0,15 96 ambiente 1,5 g, 4 %
5
35 (3,52) 2,5 1,0 -10 0,15 46 ambiente 2,4 g, 21 %
6
35 (3,52) 2,5 1,0 -10 0,15 25 50 3,4 g, 53 %
7
35 (3,52) 2,5 1,0 -10 0,15 7 60 1,49 g, 80 %
31

Claims (1)

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ES09717420.5T 2008-03-07 2009-03-06 Síntesis de carbonatos cíclicos Active ES2527520T3 (es)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB0804345 2008-03-07
GB0804345A GB0804345D0 (en) 2008-03-07 2008-03-07 synthesis of cyclic carbonates
GB0821092 2008-11-18
GB0821092A GB0821092D0 (en) 2008-11-18 2008-11-18 Sythesis of cyclic carbonates
PCT/GB2009/000624 WO2009109765A1 (en) 2008-03-07 2009-03-06 Synthesis of cyclic carbonates

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ES2527520T3 true ES2527520T3 (es) 2015-01-26

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US (2) US20110015409A1 (es)
EP (1) EP2257559B1 (es)
CN (1) CN102015732A (es)
BR (1) BRPI0908982B8 (es)
ES (1) ES2527520T3 (es)
WO (1) WO2009109765A1 (es)

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