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WO2018140149A1 - Procédé de transalkylation et composition catalytique utilisée dans celui-ci - Google Patents

Procédé de transalkylation et composition catalytique utilisée dans celui-ci Download PDF

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Publication number
WO2018140149A1
WO2018140149A1 PCT/US2017/066633 US2017066633W WO2018140149A1 WO 2018140149 A1 WO2018140149 A1 WO 2018140149A1 US 2017066633 W US2017066633 W US 2017066633W WO 2018140149 A1 WO2018140149 A1 WO 2018140149A1
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Prior art keywords
stream
transalkylation
poly
zeolite
alkylation
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PCT/US2017/066633
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English (en)
Inventor
Brett T. LOVELESS
Jean W. Beeckman
Christopher G. Oliveri
Scott J. WEIGEL
Matthew S. IDE
Theresa A. BAUMRUCKER
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Exxonmobil Chemical Patents Inc.
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Application filed by Exxonmobil Chemical Patents Inc. filed Critical Exxonmobil Chemical Patents Inc.
Priority to CN201780084450.5A priority Critical patent/CN110214131B/zh
Priority to JP2019560040A priority patent/JP6914362B2/ja
Priority to KR1020197021669A priority patent/KR102315640B1/ko
Priority to SG11201906175SA priority patent/SG11201906175SA/en
Priority to US16/472,610 priority patent/US20200385322A1/en
Priority to RU2019126013A priority patent/RU2753341C2/ru
Priority to CA3049411A priority patent/CA3049411C/fr
Priority to ES17823004T priority patent/ES2902875T3/es
Priority to EP17823004.1A priority patent/EP3573942B1/fr
Publication of WO2018140149A1 publication Critical patent/WO2018140149A1/fr
Priority to ZA2019/04080A priority patent/ZA201904080B/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
    • C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
    • C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
    • C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
    • 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

Definitions

  • the present invention relates to a process for the transalkylation of aromatics, particularly the transalkylation of poly-isopropylbenzene (PIPB) with benzene to produce cumene and the transalkylation of poly-ethylbenzene (PEB) with benzene to produce ethylbenzene.
  • PIPB poly-isopropylbenzene
  • PEB poly-ethylbenzene
  • Ethylbenzene is a valuable commodity chemical and is used in the production of styrene monomer. Cumene (isopropylbenzene) is also a valuable commodity chemical and is used in the production of phenol and acetone.
  • ethylbenzene is often produced by a liquid phase alkylation process from benzene and ethylene in the presence of an alkylation catalyst.
  • the liquid phase process operates at a lower temperature than its vapor phase counterpart.
  • One advantage of the liquid phase alkylation is a lower yield of undesired by-products, poly-alkylated aromatic compound(s).
  • the alkylation of aromatic hydrocarbon compounds employing zeolite catalysts is known and understood in the art.
  • U.S. Pat. No. 5,334,795 describes the liquid phase alkylation of benzene with ethylene in the presence of MCM-22 to produce ethylbenzene; and
  • U.S. Pat. No. 4,891,458 discloses liquid phase alkylation and transalkylation processes using zeolite beta.
  • Cumene is often produced by a liquid phase alkylation process from benzene and propylene in the presence of a zeolite-based alkylation catalyst.
  • U.S. Pat. No. 4,992,606 discloses a process for preparing cumene using MCM-22 in liquid phase.
  • poly-alkylated aromatic compound(s) may be transalkylated with benzene or other alkylatable aromatic compound(s) to produce additional ethylbenzene or cumene.
  • This transalkylation reaction may be accomplished by feeding the poly-alkylated aromatic compound(s) through a transalkylation reactor operated under suitable conditions and in the presence of a transalkylation catalyst.
  • 5,557,024 discloses a process for preparing short chain alkyl aromatic compounds using MCM-56 and the use of zeolite catalysts such as MCM-22, zeolite X, zeolite Y and zeolite beta for the transalkylation of the poly-alkylated aromatic compound(s).
  • a higher- activity transalkylation catalyst composition may be produced by increasing the external surface area/volume (SA/V) ratio of the transalkylation catalyst composition to a selected range of 30 cm 1 to 85 cm 1 combined with reducing the silica-to-alumina (Si/Ak) molar ratio of the zeolite in the composition to a range of 10 to 15.
  • SA/V external surface area/volume
  • Si/Ak silica-to-alumina
  • the invention is a process for producing ethylbenzene or cumene comprising one or more steps.
  • a transalkylation catalyst composition described below, is provided to a reaction zone.
  • a stream comprising poly-alkylated benzene and an alkylatable aromatic compound stream comprising benzene are provided to the reaction zone.
  • the poly-alkylated benzene stream comprises di-ethylbenzene or di-isopropylbenzene.
  • step (c) the poly-alkylated benzene stream is contacted with the benzene stream in the presence of the aforementioned transalkylation catalyst composition under at least partial liquid phase transalkylation conditions to produce a transalkylation effluent stream.
  • Such effluent comprises ethylbenzene or cumene.
  • the liquid phase transalkylation conditions include a temperature of 100°C to 300°C and a pressure of 200 kPa-a to 6000 kPa-a.
  • the catalytic activity of the transalkylation catalyst composition of this invention is higher (i.e., lower molar silica-content) than the catalytic activity of a lower- activity (i.e., higher molar silica-content) transalkylation catalyst composition which comprises said zeolite and has a silica-alumina molar ratio in the range of 25 to 37 when the catalysts are compared under equivalent transalkylation conditions.
  • the higher- activity (i.e., lower silica- content) transalkylation catalyst composition of this invention when employed in a process for producing ethylbenzene or cumene, exhibits a weight hourly space velocity of the poly- alkylated benzene stream that is higher than the weight hourly space velocity of a lower-activity (i.e., higher silica-content) transalkylation catalyst composition employed in such process, where the catalysts are compared under equivalent transalkylation conditions.
  • a portion of the stream comprising benzene is contacted with an alkylating agent stream under alkylation conditions and in the presence of an alkylation catalyst to produce an alkylation effluent which comprises a mono-alkylated benzene and the poly-alkylated benzene. Thereafter, the alkylation effluent is separated to recover the poly-alkylated benzene stream in which a portion is supplied to step (b) of the process for producing ethylbenzene or cumene.
  • the benzene stream is an impure stream which further comprises nitrogenous impurities.
  • the impure stream is contacted with a treatment material under treatment conditions to remove at least a portion of the nitrogenous impurities.
  • the treatment material is selected from the group consisting of clay, resin, activated alumina, a molecular sieve and combinations thereof.
  • the present invention is a transalkylation catalyst which comprises a zeolite having a framework structure selected from the group consisting of FAU, BEA*, MOR, MWW and mixtures thereof.
  • the zeolite has a silica-alumina molar ratio in a range of 10 to 15.
  • the transalkylation catalyst composition has an external surface area/volume ratio in the range of 30 cm 1 to 85 cm 1 .
  • the catalytic activity of the transalkylation catalyst composition is higher than the catalytic activity of a higher silica-content transalkylation catalyst composition which comprises the zeolite and has a silica-alumina molar ratio in the range of 25 to 37 when the catalysts are compared under equivalent transalkylation conditions.
  • transalkylation catalyst composition of this invention when used in a process for producing a mono-alkylated aromatic compound, preferably ethylbenzene or cumene, by the transalkylation of a poly- alkylated aromatic compound with an alkylatable aromatic compound, preferably benzene, in the presence of such composition under at least partial liquid phase transalkylation conditions.
  • a mono-alkylated aromatic compound preferably ethylbenzene or cumene
  • the external surface area/volume ratio of transalkylation catalyst composition is increased to a selected range of 30 cm 1 to 85 cm 1 , and the silica-to-alumina (Si/Ah) molar ratio of the zeolite is reduced to a selected range of 10 to 15.
  • the zeolite has a framework structure selected from the group consisting of FAU, BEA*, MOR, MWW and mixtures thereof.
  • alkylatable aromatic compound as used herein means an aromatic compound that may receive an alkyl group.
  • alkylatable aromatic compound is benzene.
  • alkylating agent means a compound which may donate an alkyl group to an alkylatable aromatic compound.
  • alkylating agent ethylene, propylene, and butylene.
  • Another non-limiting example is any poly alkylated aromatic compound that is capable of donating an alkyl group to an alkylatable aromatic compound.
  • aromatic as used herein in reference to the alkylatable aromatic compounds which are useful herein is to be understood in accordance with its art-recognized scope which includes substituted and unsubstituted mono- and polynuclear compounds.
  • Compounds of an aromatic character which possess a heteroatom e.g., N or S are also useful provided they do not act as catalyst poisons, as defined below, under the reaction conditions selected.
  • At least partial liquid phase means a mixture having at least 1 wt.% liquid phase, optionally at least 5 wt.% liquid phase, at a given temperature, pressure, and composition.
  • framework type as used herein has the meaning described in the "Atlas of Zeolite Framework Types," by Ch. Baerlocher, W.M. Meier and D.H. Olson (Elsevier, 5th Ed., 2001).
  • MCM-22 family material (or “MCM-22 family molecular sieve”), as used herein, can include:
  • a unit cell is a spatial arrangement of atoms which is tiled in three-dimensional space to describe the crystal as described in the "Atlas of Zeolite Framework Types," by Ch. Baerlocher, W.M. Meier and D.H. Olson (Elsevier, 5th Ed., 2001);
  • molecular sieves made from common second degree building blocks, "layers of one or more than one unit cell thickness", wherein the layer of more than one unit cell thickness is made from stacking, packing, or binding at least two monolayers of one unit cell thick of unit cells having the MWW framework topology.
  • the stacking of such second degree building blocks can be in a regular fashion, an irregular fashion, a random fashion, and any combination thereof; or
  • the MCM-22 family materials are characterized by having an X-ray diffraction pattern including d-spacing maxima at 12.4+0.25, 3.57+0.07 and 3.42+0.07 Angstroms (either calcined or as-synthesized).
  • the MCM-22 family materials may also be characterized by having an X-ray diffraction pattern including d-spacing maxima at 12.4+0.25, 6.9+0.15, 3.57+0.07 and 3.42+0.07 Angstroms (either calcined or as-synthesized).
  • the X-ray diffraction data used to characterize the molecular sieve are obtained by standard techniques using the K- alpha doublet of copper as the incident radiation and a diffractometer equipped with a scintillation counter and associated computer as the collection system.
  • MCM-22 Members of the MCM-22 family include, but are not limited to, MCM-22 (described in U.S. Patent No. 4,954,325), PSH-3 (described in U.S. Patent No. 4,439,409), SSZ-25 (described in U.S. Patent No. 4,826,667), ERB-1 (described in European Patent 0293032), ITQ-1 (described in U.S. Patent No. 6,077,498), ITQ-2 (described in International Patent Publication No. WO97/17290), ITQ-30 (described in International Patent Publication No. WO2005118476), MCM-36 (described in U.S. Patent No. 5,250,277), MCM-49 (described in U.S. Patent No.
  • zeolites to be included in the MCM-22 family are UZM-8 (described in U.S. Patent No. 6,756,030) and UZM-8HS (described in U.S. Patent No. 7,713,513), UZM-37 (described in U.S. Patent No. 8,158,105), all of which are also suitable for use as the molecular sieve of the MCM-22 family.
  • the molecular sieve of the MCM-22 family is in the hydrogen form and having hydrogen ions, for example, acidic.
  • the molecular sieve of the MCM-22 family is in the hydrogen form and having hydrogen ions, for example, acidic.
  • mono- alkylated aromatic compound means an aromatic compound that has only one alkyl substituent.
  • mono- alkylated aromatic compounds are ethylbenzene, iso-propylbenzene (cumene) and sec-butylbenzene.
  • poly- alkylated aromatic compound as used herein means an aromatic compound that has more than one alkyl substituent.
  • a non-limiting example of a poly- alkylated aromatic compound is poly-ethylbenzene, e.g., di-ethylbenzene, tri-ethylbenzene, and poly-isopropylbenzene, e.g., di-isopropylbenzene, and tri-isopropylbenzene.
  • regenerated when used in connection with the alkylation catalyst or the trans alkylation catalyst herein means an at least partially deactivated catalyst that has been treated under controlled conditions of oxygen content and temperature to remove at least a portion of the coke deposited or to remove at least a portion of adsorbed catalyst poisons and thereby increase the catalytic activity of such material or catalyst.
  • freshness when used in connection with the molecular sieve, the guard bed material, the alkylation catalyst, or the transalkylation catalyst herein means the molecular sieve or such catalyst has not been used in a catalytic reaction after being manufactured.
  • impurities includes, but is not limited to, compounds having at least one of the following elements: nitrogen, halogens, oxygen, sulfur, arsenic, selenium, tellurium, phosphorus, and Group 1 through Group 12 metals.
  • the invention is a process for producing a mono- alkylated aromatic compound, preferably, ethylbenzene or cumene, comprising one or more steps.
  • a transalkylation catalyst composition described herein, is provided to a reaction zone.
  • a stream comprising poly-alkylated benzene and an alkylatable aromatic compound stream comprising benzene are provided to the reaction zone.
  • the poly- alkylated benzene stream used to produce ethylbenzene comprises di-ethylbenzene.
  • the poly- alkylated benzene stream used to produce cumene is di-isopropylbenzene.
  • step (c) of the process the poly-alkylated benzene stream is contacted with the benzene stream in the presence of the aforementioned transalkylation catalyst composition under at least partial liquid phase transalkylation conditions to produce a transalkylation effluent stream comprising ethylbenzene or cumene.
  • the products of the transalkylation reaction of the invention include ethylbenzene from the transalkylation reaction of a poly-ethylbenzene, such as di-ethylbenzene, with benzene, or cumene from the transalkylation reaction of poly-isopropylbenzene, such as di- isopropylbenzene, with benzene.
  • the transalkylation effluent is separated in a conventional separation system to recover the desired ethylbenzene stream or a cumene stream.
  • a conventional separation system includes, for example, a benzene column, an ethylbenzene or cumene column, and a poly- alkylated column to recover the poly-ethylbenzene stream or the poly-isopropylbenzene stream.
  • the poly-alkylated benzene stream is produced from an alkylation process step which is particularly intended to produce mono- alkylated aromatic compounds, such as ethylbenzene and cumene in an alkylation step; however, the alkylation step will normally produce some poly-alkylated aromatic compounds, such as poly-ethylbenzene or poly- isopropylbenzene.
  • an alkylation step a portion of the stream comprising benzene, or a portion thereof, is contacted with a stream comprising an alkylating agent under alkylation conditions and in the presence of an alkylation catalyst to produce an alkylation effluent.
  • This effluent stream comprises mono-alkylated benzene and poly-alkylated benzene stream.
  • the alkylating agent is ethylene and used to alkylate benzene to produce ethylbenzene, or propylene and used to alkylate benzene to produce cumene.
  • the mono-alkylated benzene is ethylbenzene and said poly-alkylated benzene is poly-ethylbenzene.
  • the mono-alkylated benzene is cumene and said poly-alkylated benzene is poly- isopropylbenzene.
  • the alkylation effluent is separated to recover said poly-alkylated benzene stream.
  • the recovered poly-alkylated benzene stream may then be supplied to step (b) of the process to produce ethylbenzene or cumene.
  • the stream comprising benzene is an impure stream which further comprises nitrogenous impurities.
  • the process of this invention may further comprising the step of contacting the impure stream with a treatment material under treatment conditions to remove at least a portion of the nitrogenous impurities.
  • the treatment material is selected from the group consisting of clay, resin, activated alumina, Linde type X, Linde type A and combinations thereof.
  • suitable treatment conditions include a temperature from about 30°C to 200°C, and preferably between about 60°C to 150°C, a weight hourly space velocity (WHSV) of from about 0.1 hr 1 and about 200 hr 1 , preferably from about 0.5 hr 1 to about 100 hr 1 , and more preferably from about 1.0 hr 1 to about 50 hr 1 ; and a pressure between about ambient and 3000 kPa-a.
  • WHSV weight hourly space velocity
  • the process for producing a mono-alkylated aromatic compound, such as ethylbenzene or cumene, of this invention is conducted such that the organic reactants, i.e., the alkylatable aromatic compound, e.g. the benzene, and the alkylating agent, i.e. poly- alkylated benzene or ethylene or propylene, are brought into contact with an alkylation catalyst or a transalkylation catalyst.
  • the contact is made in a suitable reaction zone such as, for example, in a flow reactor containing a fixed bed of the catalyst composition, under effective alkylation or transalkylation conditions.
  • Such conditions include at least partial liquid phase transalkylation conditions or at least partial liquid phase alkylation conditions.
  • the reactants can be neat, i.e., free from intentional admixture or dilution with other material, or they can include carrier gases or diluents such as, for example, hydrogen or nitrogen.
  • the at least partial liquid phase conditions for transalkylation can include at least one of the following: a temperature of about 100°C to about 300°C, or from about 150°C to about 260°C, a pressure of about 200 kPa to about 6000 kPa, or about 200kPa to about 500 kPa, a weight hourly space velocity (WHSV) based on the total feed of about 0.5 hr 1 to about 100 hr 1 on total feed, and aromatic/poly- alkylated aromatic compound weight ratio 1 : 1 to 6: 1.
  • WHSV weight hourly space velocity
  • the transalkylation conditions include a temperature of from about 220°C to about 260°C, a pressure of from about 300 kPa to about 400 kPa, weight hourly space velocity of 2 to 6 on total feed and benzene/PEB weight ratio 2: 1 to 6: 1.
  • the conditions for transalkylation include a temperature of from about 100°C to about 200°C, a pressure of from about 300 kPa to about 400 kPa, a weight hourly space velocity of 1 to 10 on total feed and benzene/PIPB weight ratio 1: 1 to 6: 1.
  • the at least partial liquid phase conditions for alkylation can include at least one of the following: a temperature of from about 10°C and about 400°C, or from about 10°C to about 200°C, or from about 150°C to about 300°C, a pressure up to about 25000 kPa, or up to about 20000 kPa, or from about 100 kPa to about 7000 kPa, or from about 689 kPa to about 4601 kPa, a molar ratio of alkylatable aromatic compound to alkylating agent of from about 0.1 : 1 to about 50: 1, preferably from about 0.5: 1 to 10: 1, and a feed weight hourly space velocity (WHSV) of between about 0.1 and about 100 hr 1 , or from about 0.5 to 50 hr 1 , or from about 10 hr 1 to about 100 hr 1 .
  • WHSV feed weight hourly space velocity
  • the alkylation reaction may be carried out under at least partially liquid phase conditions for alkylation which include a temperature between about 150°C and 300°C, or between about 200°C and 260°C, a pressure up to about 20000 kPa, preferably from about 200 kPa to about 5600 kPa, a WHSV of from about 0.1 hr 1 to about 50 hr 1 , or from about 1 hr 1 and about 10 hr 1 based on the ethylene feed, and a ratio of the benzene to the ethylene in the alkylation reactor from 1 : 1 to 30: 1 molar, preferably from about 1 : 1 to 10: 1 molar.
  • liquid phase conditions for alkylation which include a temperature between about 150°C and 300°C, or between about 200°C and 260°C, a pressure up to about 20000 kPa, preferably from about 200 kPa to about 5600 kPa, a WHSV of from about 0.1 hr 1
  • the reaction may be carried out under at least partially liquid phase conditions for alkylation which include a temperature of up to about 250°C, preferably from about 10°C to about 200°C; a pressure up to about 25000 kPa, preferably from about 100 kPa to about 3000 kPa; and a WHSV of from about 1 hr 1 to about 250 hr 1 , preferably from 5 hr 1 to 50 hr 1 , preferably from about 5 hr 1 to about 10 hr 1 based on the ethylene feed.
  • liquid phase conditions for alkylation which include a temperature of up to about 250°C, preferably from about 10°C to about 200°C; a pressure up to about 25000 kPa, preferably from about 100 kPa to about 3000 kPa; and a WHSV of from about 1 hr 1 to about 250 hr 1 , preferably from 5 hr 1 to 50 hr 1 , preferably from about 5 hr 1 to about 10
  • Substituted alkylatable aromatic compounds which can be alkylated herein must possess at least one hydrogen atom directly bonded to the aromatic nucleus.
  • the aromatic rings can be substituted with one or more alkyl, aryl, alkaryl, alkoxy, aryloxy, cycloalkyl, halide, and/or other groups which do not interfere with the alkylation reaction.
  • Suitable alkylatable aromatic hydrocarbons for any one of the embodiments of this invention include benzene, naphthalene, anthracene, naphthacene, perylene, coronene, and phenanthrene, with benzene being preferred.
  • alkyl substituted aromatic compounds for any one of the embodiments of this invention include toluene (also preferred), xylene, isopropylbenzene, normal propylbenzene, alpha-methylnaphthalene, ethylbenzene, cumene, mesitylene, durene, p- cymene, butylbenzene, pseudocumene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, isoamylbenzene, isohexylbenzene, pentaethylbenzene, pentamethylbenzene; 1,2,3,4- tetraethylbenzene
  • alkylate is obtained as a high boiling fraction in which the alkyl group attached to the aromatic nucleus varies in size from about Ce to about Ci 2 .
  • cumene or ethylbenzene is the desired product, the present process produces acceptably little by-products such as xylenes.
  • the xylenes made in such instances may be less than about 500 ppm.
  • Reformate containing substantial quantities of benzene, toluene and/or xylene constitutes a useful feed for the process of this invention.
  • the alkylating agents which are useful in one or more embodiments of this invention, generally include any aliphatic or aromatic organic compound having one or more available alkylating olefinic groups capable of reaction with the alkylatable aromatic compound.
  • the alkylating agent comprises an olefinic group having from 1 to 5 carbon atoms, or a poly-alkylated aromatics compound(s). More preferably, the alkylation agents are poly-ethylbenzene and poly-isopropylbenzene for the transalkylation reaction, and ethylene and propylene for the alkylation reaction.
  • alkylating agents for any one of the embodiments of this invention are olefins, preferably, ethylene, propylene, the butenes, and the pentenes, and mixtures thereof; alcohols (inclusive of monoalcohols, dialcohols, trialcohols, etc.), such as methanol, ethanol, the propanols, the butanols, and the pentanols; aldehydes such as formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, and n-valeraldehyde; and alkyl halides such as methyl chloride, ethyl chloride, the propyl chlorides, the butyl chlorides, and the pentyl chlorides, and so forth.
  • alcohols inclusivee of monoalcohols, dialcohols, trialcohols, etc.
  • aldehydes such as formaldehyde, acetaldehyde, prop
  • Mixtures of light olefins are especially useful as alkylating agents in the alkylation process of this invention. Accordingly, mixtures of ethylene, propylene, butenes, and/or pentenes which are major constituents of a variety of refinery streams, e.g., fuel gas, gas plant off-gas containing ethylene, propylene, etc., naphtha cracker off-gas containing light olefins, refinery FCC propane/propylene streams, etc., are useful alkylating agents herein.
  • refinery streams e.g., fuel gas, gas plant off-gas containing ethylene, propylene, etc.
  • naphtha cracker off-gas containing light olefins e.g., refinery FCC propane/propylene streams, etc.
  • Poly-alkylated aromatic compounds suitable for one or more embodiments of this invention include, but are not limited to, di-ethylbenzenes, tri-ethylbenzenes and poly- ethylbenzene(s), as well as di-isopropylbenzenes (DIPBs), tri-isopropylbenzenes (TIPBs) and poly-isopropylbenzene(s) or mixtures thereof.
  • DIPBs di-isopropylbenzenes
  • TIPBs tri-isopropylbenzenes
  • poly-isopropylbenzene(s) or mixtures thereof are examples of poly-isopropylbenzene(s) or mixtures thereof.
  • the alkylatable aromatic compound stream and the alkylating agent stream supplied to the present process are impure streams and will contain some level of reactive impurities (as defined above), such as, for example, nitrogen compounds, which are small enough to enter the pores of the catalyst, preferably alkylation catalyst and/or trans alkylation catalyst, and thereby poison the catalyst.
  • reactive impurities such as, for example, nitrogen compounds
  • it is normal to supply all alkylatable aromatic compounds to the first alkylation and/or transalkylation reaction zone, but to divide and supply the alkylating agent between the alkylation and/or transalkylation catalyst beds.
  • the catalyst in the first reaction zone is more likely to be poisoned by impurities.
  • the present process preferably employs a separate guard bed in the first alkylation and/or transalkylation reaction zone.
  • the guard bed may be upstream of and separate from the first reaction zone.
  • the effluent from the guard bed is a treated feed, such as, for example, a treated alkylatable aromatic compound and/or a treated alkylating agent, which is then fed to the process of this invention.
  • the process of the invention in one or more embodiments, further comprises the step of contacting said alkylatable aromatic compound and/or said alkylating agent with a treatment material to remove at least a portion of any impurities from said alkylatable aromatic compound or said alkylating agent.
  • the treatment material may be selected from the group consisting of clay, resin, activated alumina, a molecular sieve and combinations thereof.
  • the molecular sieve may be selected from the group consisting Linde X, Linde A, zeolite beta, faujasite, zeolite Y, Ultrastable Y (USY), Dealuminized Y (Deal Y), Rare Earth Y (REY), Ultrahydrophobic Y (UHP-Y), mordenite, TEA-mordenite, ZSM-3, ZSM-4, ZSM-14, ZSM- 18, ZSM-20 and combinations thereof.
  • the present invention is a transalkylation catalyst which comprises a zeolite having a framework structure selected from the group consisting of FAU, BEA*, MOR, MWW and mixtures thereof.
  • the zeolite has a silica-alumina molar ratio in a range of 10 to 15.
  • the transalkylation catalyst composition has an external surface area/volume ratio in the range of 30 cm 1 to 85 cm 1 , or 40 cm "1 to 80 cm 1 , or 45 cm "1 or 75 cm 1 .
  • the zeolite having a FAU framework type may be selected from the group consisting of 13X, Ultrastable Y (USY) and its low sodium variant, dealuminized Y (Deal Y), Ultrahydrophobic Y (UHP-Y), rare earth exchanged Y (REY), rare earth exchanged USY (RE- USY) and mixtures thereof.
  • the zeolite having a FAU framework type is USY.
  • the zeolite having a MOR framework type may be selected from the group consisting of mordenite, EMM-34, TEA-mordenite and mixtures thereof.
  • the zeolite having a BEA* framework type is EMM-34, which is disclosed and described in U.S. Pub. 2016-0221832.
  • the zeolite having a BEA* framework type is zeolite beta.
  • the zeolite having a MWW framework type is a MCM-22 family material.
  • MCM-22 family material may be selected from the group consisting of MCM-22, PSH-3, SSZ- 25, MCM-36, MCM-49, MCM-56, ERB-1, EMM-10, EMM-10-P, EMM-12, EMM-13, UZM- 8, UZM-8HS, ITQ-1, ITQ-2, ITQ-30 and mixtures of two or more thereof.
  • the MCM-22 family material of the zeolite having MWW framework type is MCM-22 or MCM- 49.
  • the transalkylation catalyst composition is acidic in active form and has protons.
  • the zeolite can be combined in a conventional manner with an oxide binder, such as alumina or silica, such that the final transalkylation contains between 1 and 100 wt.% of the zeolite, based on the weight of the catalyst composition.
  • the acidic transalkylation catalyst composition comprises greater than 0 wt.% up to 99 wt.% of a binder, based on the weight of said transalkylation catalyst composition.
  • the zeolite comprise from 1 wt.% up to 100 wt.%, or from 10 wt.% to 90 wt.%, or from 20 wt.% to 80 wt.% of the transalkylation catalyst composition. Preferably, the zeolite comprises from 65 wt.% to 80 wt.% of said transalkylation catalyst composition.
  • the binder may be a metal or a mixed metal oxide.
  • the binder may be selected from the group consisting of alumina, silica, titania, zirconia, tungsten oxide, ceria, niobia and combinations thereof.
  • the transalkylation catalyst composition of this invention comprises a zeolite having a framework structure selected from the group consisting of FAU, BEA*, MOR, MWW and mixtures thereof, wherein the silica-alumina molar ratio of said zeolite is in a range of 10 to 15, or in the range 11 to 14, or in the range of 12 to 13: wherein said FAU framework structure is selected from the group consisting of 13X, low sodium ultrastable Y (USY), dealuminized Y (Deal Y), ultrahydrophobic Y (UHP-Y), rare earth exchanged Y (REY), rare earth exchanged USY (RE-USY), and mixtures thereof,
  • said zeolite which has said BEA* framework structure is zeolite beta
  • said zeolite which has MOR framework structure is selected from the group consisting of mordenite, EMM-34, TEA-mordenite, and mixtures thereof;
  • said zeolite which has said MWW framework structure is a MCM-22 family material
  • said MCM-22 family molecular sieve is any one of MCM-22, PSH-3, SSZ-25, MCM-36, MCM-49, MCM-56, ERB-1, EMM- 10, EMM-10-P, EMM- 12, EMM- 13, UZM-8, UZM-8HS, UZM-37, ITQ-1, ITQ-2, ITQ-30, or combinations of two or more thereof;
  • transalkylation catalyst has an external surface area/volume ratio in the range of 30 cm 1 to 85 cm 1 ;
  • said zeolite comprises from 65 wt.% to 80 wt.% of said transalkylation catalyst composition.
  • the catalytic activity of the transalkylation catalyst composition of this invention is higher than the catalytic activity of a lower-activity (i.e., higher molar silica-content) transalkylation catalyst composition which comprises said zeolite and has a silica-alumina (Si/Ak) molar ratio in the range of 25 to 37, or in the range 27 to 35, or in the range 29 to 33, when the catalysts are compared under equivalent transalkylation conditions.
  • the higher catalytic activity of the transalkylation catalyst of this invention is achieved by decreasing the amount of silica in the composition which results in a lower silica-alumina molar ratio.
  • the higher- activity (i.e., lower silica-content) transalkylation catalyst composition of this invention when employed in a process for producing ethylbenzene or cumene, exhibits a weight hourly space velocity of the poly- alkylated benzene stream that is higher than the weight hourly space velocity of a lower- activity (i.e., higher silica-content) transalkylation catalyst composition employed in such process, where the catalysts are compared under equivalent transalkylation conditions, such as equivalent transalkylation temperatures.
  • the higher-activity (i.e., lower silica-content) transalkylation catalyst composition of this invention when employed in a process for producing ethylbenzene or cumene may be operated at a lower transalkylation temperature than that of a lower-activity (i.e., higher silica-content) transalkylation catalyst composition employed in such process, where the catalysts are compared under equivalent transalkylation conditions.
  • the higher activity exhibited by the transalkylation catalyst composition of this invention is provided by the lower silica- alumina (Si/Ah) molar ratio of the zeolite combined with the higher external surface area/volume (SA/V) of the composition.
  • Si/Ah silica- alumina
  • SA/V external surface area/volume
  • the lower Si/ Ah molar ratio provides higher alumina content which facilitates the transalkylation reaction.
  • the higher SA/V ratio provides an increased surface area per unit volume for the transalkylation of the bulky reactants. This is particularly true of a reaction in the liquid phase.
  • the alkylation catalyst comprises an aluminosilicate.
  • the aluminosilicate is any one of a MCM-22 family molecular sieve, faujasite, mordenite, zeolite-beta, or combinations of two or more thereof.
  • the MCM-22 family molecular sieve is any one of MCM-22, PSH-3, SSZ-25, MCM-36, MCM-49, MCM-56, ERB-1, EMM- 10, EMM-10-P, EMM-12, EMM-13, UZM-8, UZM-8HS, UZM-37, ITQ-1, ITQ-2, ITQ-30, or combinations of two or more thereof.
  • the alkylation catalyst is acidic in active form and has protons.
  • the zeolite can be combined in a conventional manner with an oxide binder, such as alumina or silica, such that the final alkylation catalyst composition contains between 1 and 100 wt.% of the zeolite, based on the weight of said alkylation catalyst composition.
  • the acidic alkylation catalyst composition comprises greater than 0 wt.% up to 99 wt.% of a binder, based on the weight of said alkylation catalyst composition.
  • the zeolite comprise from 1 wt.% up to 100 wt.%, or from 10 wt.% to 90 wt.%, or from 20 wt.% to 80 wt.% of the alkylation catalyst composition.
  • the zeolite comprises from 65 wt.% to 80 wt.% of said alkylation catalyst composition.
  • the binder may be a metal or a mixed metal oxide.
  • the binder may be selected from the group consisting of alumina, silica, titania, zirconia, tungsten oxide, ceria, niobia and combinations thereof.
  • said alkylation or transalkylation catalyst composition can be a fresh alkylation or transalkylation catalyst composition, an at least partially deactivated alkylation or transalkylation catalyst composition, or combinations thereof.
  • said at least partially deactivated alkylation or transalkylation catalyst was deactivated by coke deposition during its prior use in an alkylation or transalkylation process.
  • the alkylation and/or transalkylation catalyst composition will gradually lose its alkylation activity, such that the reaction temperature required to achieve a given performance parameter, such as, for example, conversion of the alkylating agent, will increase.
  • a given performance parameter such as, for example, conversion of the alkylating agent
  • the deactivated catalyst composition can be subjected to a regeneration procedure using any known method, such as the method disclosed in U.S. Patent No. 6,380,119 to BASF, incorporated herein by reference.
  • PEB poly-ethylbenzenes
  • DEB di-ethylbenzene
  • the test procedure consisted of loading the dried catalyst into a batch reactor along with benzene. The reactor was then heated to 266°F (130°C) followed by the addition of PEB under an inert gas pressure of 300 psig (2068.43 kPa).
  • Catalyst A the benzene/PEB ratio of 2: 1 by weight and the weight hourly space velocity (WHSV) of 1.1 hr 1 were set, and the reaction temperature increased stepwise to 190°C to achieve a target DEB conversion of 65%.
  • Catalyst B the benzene/PEB ratio of 2:1 by weight and the weight hourly space velocity (WHSV) of 1.1 hr 1 were set, and the reaction temperature decreased stepwise to 177°C to achieve a target DEB conversion of 65%. Samples were removed periodically for the duration of the test and analyzed with gas chromatography to determine the conversion of DEB.
  • Table 1 shows the performance data of Catalyst A and Catalyst B the transalkylation of poly-ethylbenzenes (PEB) with benzene as follows:
  • SA/V surface/volume
  • the transalkylation of poly-ethylbenzenes (PEB) with benzene was performed in a fixed bed reactor with Catalyst C and Catalyst D and for Catalyst E and Catalyst F.
  • the test procedure used was the same as described above.
  • the Transalkylation activity was based on the DEB conversion.
  • the transalkylation activity for Catalyst D was normalized to the transalkylation activity for Catalyst C.
  • the transalkylation activity for Catalyst F was normalized to the transalkylation activity for Catalyst W.
  • Table 2 shows that the modification of the catalyst extrudate particle size and shape can influence significantly the transalkylation activity. Catalyst particles with smaller diameters and larger surface area to volume ratios are preferred for liquid phase reactions where mass transport limitations may persist.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de production d'un composé aromatique mono-alkylé, tel que, par exemple, l'éthylbenzène ou le cumène, dans lequel un flux de composé aromatique pouvant être alkylé, tel que, par exemple, le benzène et un flux d'agent d'alkylation, tel que, par exemple, le poly-éthylbenzène ou le poly-isopropylbenzène, sont mis en contact en présence d'un catalyseur de transalkylation et dans au moins des conditions de transalkylation en phase liquide partielle. Le catalyseur de transalkylation comprend une zéolite ayant une structure choisie dans le groupe constitué par FAU, BEA*, MOR, MWW et des mélanges de ceux-ci. La zéolite a un rapport molaire silice-alumine dans une plage de 10 à 15. La composition catalytique de transalkylation a un rapport surface externe/volume dans la plage de 30 cm 1 à 85 cm 1.
PCT/US2017/066633 2017-01-25 2017-12-15 Procédé de transalkylation et composition catalytique utilisée dans celui-ci WO2018140149A1 (fr)

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CN201780084450.5A CN110214131B (zh) 2017-01-25 2017-12-15 烷基转移方法及其所用的催化剂组合物
JP2019560040A JP6914362B2 (ja) 2017-01-25 2017-12-15 トランスアルキル化プロセスおよびそれに使用される触媒組成物
KR1020197021669A KR102315640B1 (ko) 2017-01-25 2017-12-15 트랜스알킬화 방법 및 이에 사용되는 촉매 조성물
SG11201906175SA SG11201906175SA (en) 2017-01-25 2017-12-15 Transalkylation process and catalyst composition used therein
US16/472,610 US20200385322A1 (en) 2017-01-25 2017-12-15 Transalkylation Process and Catalyst Composition Used Therein
RU2019126013A RU2753341C2 (ru) 2017-01-25 2017-12-15 Способ трансалкилирования и применяющаяся в нем каталитическая композиция
CA3049411A CA3049411C (fr) 2017-01-25 2017-12-15 Procede de transalkylation et composition catalytique utilisee dans celui-ci
ES17823004T ES2902875T3 (es) 2017-01-25 2017-12-15 Procedimiento de transalquilación y composición de catalizador utilizada en el mismo
EP17823004.1A EP3573942B1 (fr) 2017-01-25 2017-12-15 Procédé de transalkylation et composition de catalyseur utilisé dans celui-ci
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RU2779556C1 (ru) * 2021-06-08 2022-09-09 Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") Способ получения изопропилбензола трансалкилированием диизопропилбензолов с бензолом
US11820723B2 (en) 2019-10-17 2023-11-21 Exxonmobil Chemicals Patents Inc. Production of alkylaromatic compounds
US11827593B2 (en) 2019-10-17 2023-11-28 Exxonmobil Chemicals Patents Inc. Production of alkylaromatic compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11820723B2 (en) 2019-10-17 2023-11-21 Exxonmobil Chemicals Patents Inc. Production of alkylaromatic compounds
US11827593B2 (en) 2019-10-17 2023-11-28 Exxonmobil Chemicals Patents Inc. Production of alkylaromatic compounds
WO2022098453A1 (fr) 2020-11-06 2022-05-12 Exxonmobil Chemical Patents Inc. Production de composés alkylaromatiques
RU2779556C1 (ru) * 2021-06-08 2022-09-09 Публичное акционерное общество "Нефтяная компания "Роснефть" (ПАО "НК "Роснефть") Способ получения изопропилбензола трансалкилированием диизопропилбензолов с бензолом

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