ES2653794T3 - Procedimiento para la fabricación de un 1,2-epóxido y un dispositivo para llevar a cabo dicho procedimiento - Google Patents

Procedimiento para la fabricación de un 1,2-epóxido y un dispositivo para llevar a cabo dicho procedimiento Download PDF

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ES2653794T3
ES2653794T3 ES15171187.6T ES15171187T ES2653794T3 ES 2653794 T3 ES2653794 T3 ES 2653794T3 ES 15171187 T ES15171187 T ES 15171187T ES 2653794 T3 ES2653794 T3 ES 2653794T3
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aqueous phase
range
terminal olefin
organic phase
oxidant
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Prasad Muppa
Ron Postma
Bart B. van den Berg
Jürgen STOCK
Holger Wiederhold
Hans-Martin Rausch
Jörg SCHALLENBERG
Stefan Bernhardt
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Evonik Operations GmbH
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Evonik Degussa GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
    • B01D17/02—Separation of non-miscible liquids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
    • B01D17/02—Separation of non-miscible liquids
    • B01D17/0208—Separation of non-miscible liquids by sedimentation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
    • B01F25/40—Static mixers
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/18—Stationary reactors having moving elements inside
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B01J19/2415—Tubular reactors
    • B01J19/2435—Loop-type reactors
    • 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
    • B01J31/1805—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 nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • B01J31/182—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine comprising aliphatic or saturated rings
    • 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
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
    • B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
    • B01F25/40—Static mixers
    • B01F25/42—Static mixers in which the mixing is affected by moving the components jointly in changing directions, e.g. in tubes provided with baffles or obstructions
    • B01F25/43—Mixing tubes, e.g. wherein the material is moved in a radial or partly reversed direction
    • B01F25/431—Straight mixing tubes with baffles or obstructions that do not cause substantial pressure drop; Baffles therefor
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00049—Controlling or regulating processes
    • B01J2219/00051—Controlling the temperature
    • B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
    • B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
    • B01J2219/00094—Jackets
    • 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
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • 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
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B01J2231/72—Epoxidation
    • 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
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese
    • 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
    • B01J2531/90—Catalytic systems characterized by the solvent or solvent system used
    • B01J2531/96—Water
    • 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
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un procedimiento para la fabricación de un epóxido, que comprende: a) añadir un oxidante, un complejo de manganeso soluble en agua y una olefina terminal para formar una mezcla de reacción multifásica de una fase acuosa y una fase orgánica con una relación volumétrica de fase acuosa a fase orgánica en el intervalo de desde 10:1 a 1:5, en donde la olefina terminal presenta una solubilidad máxima en la fase acuosa a 20 °C de 0,01 a 100 g/l y el complejo de manganeso soluble en agua es una especie mononuclear de la fórmula general (I): [LMnX3]Y (I) o una especie binuclear de la fórmula general (II): [LMn(μ-X)3MnL](Y)n (II) en donde Mn es un manganeso; L o cada L es independientemente un ligando polidentado, cada X es independientemente una especie de coordinación y cada μ-X es independientemente una especie de coordinación de puente y en donde Y es un contraión de no coordinación; b) dispersar la fase orgánica en la fase acuosa continua en la forma de gotitas menores que 3 mm y hacer reaccionar la olefina terminal con el oxidante en la mezcla de reacción multifásica que tiene al menos una fase orgánica en presencia del complejo de manganeso soluble en agua; c) separar la mezcla de reacción en la fase orgánica y una fase acuosa y d) reutilizar al menos parte de la fase acuosa y el catalizador contenido en la misma mediante reciclado de al menos una porción de la fase acuosa obtenida en la etapa c) en la etapa a).

Description

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Claims (10)

  1. 5
    10
    15
    20
    25
    30
    35
    40
    REIVINDICACIONES
    1. Un procedimiento para la fabricación de un epóxido, que comprende:
    a) añadir un oxidante, un complejo de manganeso soluble en agua y una olefina terminal para formar una mezcla de reacción multifásica de una fase acuosa y una fase orgánica con una relación volumétrica de fase acuosa a fase orgánica en el intervalo de desde 10:1 a 1:5, en donde la olefina terminal presenta una solubilidad máxima en la fase acuosa a 20 °C de 0,01 a 100 g/l y el complejo de manganeso soluble en agua es una especie mononuclear de la fórmula general (I):
    [LMnX3]Y (I)
    o una especie binuclear de la fórmula general (II):
    [LMn(µ-X)3MnL](Y)n (II)
    en donde Mn es un manganeso; L o cada L es independientemente un ligando polidentado, cada X es independientemente una especie de coordinación y cada µ-X es independientemente una especie de coordinación de puente y en donde Y es un contraión de no coordinación;
    b) dispersar la fase orgánica en la fase acuosa continua en la forma de gotitas menores que 3 mm y hacer reaccionar la olefina terminal con el oxidante en la mezcla de reacción multifásica que tiene al menos una fase orgánica en presencia del complejo de manganeso soluble en agua;
    c) separar la mezcla de reacción en la fase orgánica y una fase acuosa y
    d) reutilizar al menos parte de la fase acuosa y el catalizador contenido en la misma mediante reciclado de al menos una porción de la fase acuosa obtenida en la etapa c) en la etapa a).
  2. 2.
    El procedimiento de la reivindicación 1, en donde la relación de reciclado de agua de los componentes acuosos a fase acuosa reutilizada está en el intervalo de 10:1 a 1:10, preferiblemente en el intervalo de desde 2:1 a 1:5.
  3. 3.
    El procedimiento de la reivindicación 1 o 2, en donde la relación molar de olefina terminal a oxidante está en el intervalo de 12:1 a 1:1.
  4. 4.
    El procedimiento según una de las reivindicaciones precedentes 1 a 3, en donde la fase acuosa comprende además un sistema tampón para estabilizar el pH en el intervalo de 1 a 8 y se añade el tampón a la mezcla de reacción como un componente acuoso.
  5. 5.
    El procedimiento según una de las reivindicaciones precedentes 1 a 4, en donde la reacción se lleva a cabo a temperaturas en el intervalo de -5 °C a 40 °C.
  6. 6.
    El procedimiento según una de las reivindicaciones precedentes 1 a 5, en donde la olefina terminal se selecciona de: bromuro de alilo, cloruro de alilo y acetato de alilo.
  7. 7.
    El procedimiento según una de las reivindicaciones precedentes 1 a 5, en donde la olefina terminal es propileno.
  8. 8.
    El procedimiento según una de las reivindicaciones precedentes 1 a 7, en donde la relación molar de complejo de manganeso soluble en agua a oxidante está en el intervalo de 1:10 a 1:10 000 000.
  9. 9.
    El procedimiento según una de las reivindicaciones precedentes 1 a 8, en donde el oxidante es peróxido de hidrógeno o un precursor del mismo.
  10. 10.
    El procedimiento según una de las reivindicaciones precedentes 1 a 9, en donde el procedimiento se lleva a cabo en un reactor de tipo tanque agitado continuo o en un reactor de bucle.
    8
ES15171187.6T 2010-02-02 2011-01-26 Procedimiento para la fabricación de un 1,2-epóxido y un dispositivo para llevar a cabo dicho procedimiento Active ES2653794T3 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10001035A EP2354131A1 (en) 2010-02-02 2010-02-02 Process for the manufacture of a 1,2-epoxide and a device for carrying out said process
EP10001035 2010-02-02

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Publication Number Publication Date
ES2653794T3 true ES2653794T3 (es) 2018-02-08

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Country Link
US (2) US8859790B2 (es)
EP (3) EP2354131A1 (es)
JP (2) JP6000856B2 (es)
KR (3) KR20140056381A (es)
CN (2) CN105566250B (es)
AR (1) AR080113A1 (es)
AU (2) AU2011223288B2 (es)
BR (1) BR112012019183A8 (es)
ES (1) ES2653794T3 (es)
HU (1) HUE035587T2 (es)
MY (1) MY162533A (es)
PT (1) PT2947076T (es)
RU (1) RU2540864C2 (es)
SA (1) SA111320159B1 (es)
TW (2) TWI519526B (es)
WO (1) WO2011107188A2 (es)

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