ES2632713T3 - Proceso de alquilación que usa un catalizador que comprende zeolitas que contienen tierras raras y un metal de hidrogenación - Google Patents

Proceso de alquilación que usa un catalizador que comprende zeolitas que contienen tierras raras y un metal de hidrogenación Download PDF

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ES2632713T3
ES2632713T3 ES08708295.4T ES08708295T ES2632713T3 ES 2632713 T3 ES2632713 T3 ES 2632713T3 ES 08708295 T ES08708295 T ES 08708295T ES 2632713 T3 ES2632713 T3 ES 2632713T3
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catalyst
weight
zeolite
hydrogenation metal
alkylating agent
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Emanuel Hermanus Van Broekhoven
Mark Hendrikus Harte
Gijsbertus Klaver
Jan Nieman
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Albemarle Netherlands BV
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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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
    • B01J29/12—Noble metals
    • B01J29/126—Y-type faujasite
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B01J29/7007—Zeolite Beta
    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/90—Regeneration or reactivation
    • 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
    • B01J35/00—Catalysts, in general, characterised by their form or physical properties
    • B01J35/40—Catalysts, in general, characterised by their form or physical properties characterised by dimensions, e.g. grain size
    • 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
    • B01J38/00—Regeneration or reactivation of catalysts, in general
    • B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
    • B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
    • B01J38/56—Hydrocarbons
    • 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
    • B01J38/00—Regeneration or reactivation of catalysts, in general
    • B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
    • B01J38/50—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids
    • B01J38/58—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using organic liquids and gas addition thereto
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
    • C07C2/56—Addition to acyclic hydrocarbons
    • C07C2/58—Catalytic processes
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/30—After treatment, characterised by the means used
    • B01J2229/40—Special temperature treatment, i.e. other than just for template removal
    • 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
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/30—After treatment, characterised by the means used
    • B01J2229/42—Addition of matrix or binder particles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
    • C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
    • C07C2521/04—Alumina
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • C07C2529/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
    • C07C2529/12—Noble metals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2529/00—Catalysts comprising molecular sieves
    • C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
    • C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
    • C07C2529/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 containing iron group metals, noble metals or copper
    • C07C2529/74—Noble metals
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/70—Catalyst aspects
    • C10G2300/703—Activation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/80—Additives
    • C10G2300/805—Water
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline
    • 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)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Un proceso para la alquilación de hidrocarburos donde el isobutano se hace reaccionar con un agente de alquilación seleccionado entre alquenos C2-C6 para formar un alquilato en presencia de un catalizador que comprende un metal de hidrogenación y un constituyente de ácido sólido que contiene tierras raras, sometiéndose el catalizador de manera intermitente a una etapa de regeneración poniéndose en contacto con una alimentación que contiene un hidrocarburo saturado e hidrógeno, llevándose a cabo dicha regeneración al 90 % o menos del ciclo activo del catalizador, definiéndose el ciclo activo del catalizador como el tiempo desde el inicio de la alimentación del agente de alquilación hasta el momento en que, en comparación con la entrada de la sección de reactor que contiene el catalizador, el 20 % del agente de alquilación deja la sección de reactor que contiene el catalizador sin convertirse, sin contar la isomerización dentro de la molécula, donde dicho catalizador se regenera antes de que haya cualquier disminución sustancial de actividad de dicho catalizador, donde el metal de hidrogenación se selecciona entre platino, paladio y mezclas de los mismos, donde el constituyente de ácido sólido es una zeolita Y preparada mediante un proceso que comprende las etapas de: preparación de una zeolita de sodio, intercambio iónico de la zeolita de sodio con iones de tierras raras y, opcionalmente, iones de NH4 + para reducir el Na2O hasta aproximadamente el 3-6 % en peso, vaporización de la zeolita a de 400 a 500 °C de manera que a0 varía de 24,56 a 24,72 Å, intercambio iónico con iones de NH4 + para reducir el Na2O hasta por debajo del 1,5 % en peso y secado, y donde el contenido de agua del catalizador varía del 1,5 % al 6 % en peso, medido mediante la determinación de la pérdida de peso al calentar el catalizador durante dos horas a 600 °C (pérdida por calcinación LOI600).

Description

imagen1
imagen2
imagen3
imagen4
imagen5
Cada vez, después de 1 hora de reacción, el catalizador se regeneró mediante lavado con mezcla de isobutano/alquilado durante 5 minutos, seguido de 50 minutos de regeneración mediante el contacto con una solución de 1 % en moles de H2 en mezcla de isobutano/alquilado, y después mediante lavado con mezcla de isobutano/alquilado durante 5 minutos más (siendo 1 hora el tiempo total de lavado y regeneración). Después de
5 esta etapa de lavado, se inició de nuevo la alquilación.
La temperatura durante las etapas de lavado, la etapa de regeneración, y la etapa de reacción era la misma.
El proceso se realizó tal como se ha descrito anteriormente y el rendimiento catalítico se midió como una función de 10 tiempo.
El rendimiento estaba caracterizado por la conversión de olefina por paso de reactor y el índice de octanos de investigación (RON). El RON se determinó tal como se ha descrito en las páginas 13 y 14 del documento WO 9823560, con la única excepción de que se estimó que la contribución de RON de C9+ total (excluyendo el 2,2,5
15 trimetilhexano) era de 84 en lugar de 90.
La conversión de olefina por paso de reactor es la fracción en peso (como porcentaje) de olefinas que se convierte entre la entrada y la salida del lecho de catalizador, sin contar la isomerización dentro de las moléculas de olefina.
20 Las Figuras 1, 2 y 3 muestran los resultados de los ensayos de desactivación acelerada de los catalizadores.
La Figura 1 muestra que, en las mismas condiciones de ensayo (whsv=0,16), el nuevo catalizador (con diversas cantidades de RE en zeolita) mantiene un nivel de conversión de olefinas superior al catalizador de referencia (sin RE). La Figura 2 muestra que el nuevo catalizador permite una whsv (0,20) con velocidades de desactivación 25 similares en comparación con el catalizador de referencia. Por lo tanto, el nuevo catalizador puede operarse a mayor whsv y, como consecuencia, se necesita menos catalizador para producir una cantidad fija de alquilado, es decir, se necesita menos catalizador a capacidad constante de una planta de alquilación. La Figura 3 muestra que el nuevo catalizador produce alquilado con al menos el mismo RON que se obtiene con el catalizador de referencia. El catalizador con aproximadamente el 5 % en peso de RE en zeolita combina la estabilidad más alta con un RON
30 relativamente alto de alquilado producido.
7

Claims (1)

  1. imagen1
    imagen2
ES08708295.4T 2007-01-26 2008-01-28 Proceso de alquilación que usa un catalizador que comprende zeolitas que contienen tierras raras y un metal de hidrogenación Active ES2632713T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US89803907P 2007-01-26 2007-01-26
US898039P 2007-01-26
PCT/EP2008/050977 WO2008090234A1 (en) 2007-01-26 2008-01-28 Alkylation process using a catalyst comprising rare earth containing zeolites and a hydrogenation metal

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ES2632713T3 true ES2632713T3 (es) 2017-09-15

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US (1) US8163969B2 (es)
EP (1) EP2106394B1 (es)
JP (2) JP5486316B2 (es)
CN (1) CN101589008B (es)
BR (1) BRPI0807035B1 (es)
CA (1) CA2675937C (es)
DK (1) DK2106394T3 (es)
ES (1) ES2632713T3 (es)
HU (1) HUE035768T2 (es)
PL (1) PL2106394T3 (es)
TW (1) TWI433829B (es)
WO (1) WO2008090234A1 (es)

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US8470726B2 (en) * 2009-12-16 2013-06-25 Uop Llc Alkylation catalysts with low olefin skeletal isomerization activity
US9126184B2 (en) * 2009-12-16 2015-09-08 Uop Llc Detergent alkylation using a rare earth exchanged catalyst
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EP3167026B1 (en) * 2014-07-07 2019-05-15 Albemarle Europe Sprl. Alkylation process using a catalyst comprising cerium rich rare earth containing zeolites and a hydrogenation metal
CN106631655B (zh) * 2015-10-28 2019-05-21 中国石油化工股份有限公司 一种烷基化反应方法
RU2637922C2 (ru) * 2016-06-02 2017-12-08 Публичное акционерное общество "Электрогорский институт нефтепереработки" (ПАО "ЭлИНП") Способ алкилирования изобутана в трехфазном реакторе с неподвижным слоем катализатора
CA3054985C (en) * 2017-03-01 2022-03-01 Albemarle Europe Srl Alkylation process with improved octane number
CN110653003B (zh) * 2018-06-28 2022-08-09 中国石油化工股份有限公司 一种固体酸催化剂、制备方法及其一种烷基化反应方法
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US11098256B2 (en) 2020-01-08 2021-08-24 Saudi Arabian Oil Company Modified ultra-stable Y (USY) zeolite catalyst for improving cold flow properties of distillates
US11484869B2 (en) 2020-12-09 2022-11-01 Saudi Arabian Oil Company Modified ultra-stable Y (USY) zeolite catalyst for dealkylation of aromatics
BR102021007444A2 (pt) * 2021-04-19 2022-10-25 Petróleo Brasileiro S.A. - Petrobras Processo para a obtenção de alquil-naftênicos
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TWI433829B (zh) 2014-04-11
BRPI0807035B1 (pt) 2022-05-31
EP2106394B1 (en) 2017-05-17
JP5486316B2 (ja) 2014-05-07
TW200844076A (en) 2008-11-16
DK2106394T3 (en) 2017-07-31
US20080183025A1 (en) 2008-07-31
PL2106394T3 (pl) 2017-10-31
CN101589008A (zh) 2009-11-25
CA2675937C (en) 2015-06-16
EP2106394A1 (en) 2009-10-07
WO2008090234A1 (en) 2008-07-31
HUE035768T2 (en) 2018-05-28
JP2010516746A (ja) 2010-05-20
US8163969B2 (en) 2012-04-24
JP2014193845A (ja) 2014-10-09
JP5789315B2 (ja) 2015-10-07
BRPI0807035A2 (pt) 2014-04-22
CN101589008B (zh) 2013-06-05
CA2675937A1 (en) 2008-07-31

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