# US 7,411,101 B2 · Production of alkylaromatic compounds > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,411,101 B2 - Document ID: US7411101B2 - Status: Granted - Kind: B2 - Application number: 10/466,719 - Filed: 2002-02-06 - Published: 2004-11-04 - Granted: 2008-08-12 - Earliest claimed: 2002-02-06 - Assignees: ExxonMobil Chemical Patents Inc. - Inventors: Shiou-Shan Chen; Henry Hwang - Web page: https://patentgrep.com/patent/US7411101B2 ## CPC - C07C 15/085: Isopropylbenzene - C07C 2/66: Catalytic processes - C07C 6/126: {of more than one hydrocarbon} - C07C 15/02: Monocyclic hydrocarbons - C07C 15/073: Ethylbenzene - C07C 2521/06: Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof - C07C 2521/14: Silica and magnesia - C07C 2523/30: Tungsten - C07C 2529/08: of the faujasite type, e.g. type X or Y - C07C 2529/18: of the mordenite type - C07C 2529/40: of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11 - C07C 2529/70: of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65 - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract A process for producing a monoalkylation aromatic product, such as ethylbenzene and cumene, utilizing an alkylation reactor zone and a transalkylation zone in series or a combined alkylation and transkylation reactor zone. ## Claims ### Claim 1 A process for producing an alkylbenzene product selected from the group consisting of ethylbenzene and isopropylbenzene in a reactor having an alkylation zone in series with a transalkylation zone, said process comprising the sequential steps of: (a) introducing into the alkylation zone containing an alkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising benzene and olefin selected from the group consisting of ethylene and propylene, wherein the molar ratio of benzene to olefin is from about 1:1 to about 20:1, (b) contacting the reaction mixture of step (a) with the alkylation catalyst under reaction conditions sufficient to react essentially all the olefin to produce product comprising alkylbenzene, polyalkylbenzene and benzene, (c) introducing into the transalkylation zone containing a transalkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising the product of step (b), additional polyalkylbenzene, and optionally additional benzene, wherein the molar ratio of benzene to polyalkylbenzene is from about 0.2:1 to about 20:1, (d) contacting the reaction mixture of step (c) with the transalkylation catalyst under reaction conditions sufficient to react at least part of the beozene and polyalkylbenzene to alkylbenzene to produce product comprising alkylbenzene, polyalkylbenzene and benzene, and (e) introducing into a separation zone the product from step (d), whereby alkylbenzene, polyalkylbenzene and benzene are separated from each other, the alkylbenzene is recovered as alkylbenzene product, the benzene is added to the step (a) reaction mixture and the polyalkylbenzene is added to the step (c) reaction mixture. ### Claim 2 (depends on 1) The process of claim 1 wherein the reaction of step (b) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 3 (depends on 2) The process of claim 2 wherein the reaction of step (d) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 4 (depends on 1) The process of claim 1 wherein said polyalkylbenzene is polyethylbenzene or polyisopropylbenzene. ### Claim 5 (depends on 1) The process of claim 1 wherein said ailcylation zone and transalkylation zone are combined in the same reactor. ### Claim 6 A process for producing isopropylbenzene product in a reactor having an alkylation zone in series with a transalkylation zone, said process comprising the sequential steps of: (a) introducing into the alkylation zone containing an alkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising benzene and propylene, wherein the molar ratio of benzene to propylene is from about 1:1 toabout20:1, (b) contacting the reaction mixture of step (a) with the alkylation catalyst under reaction conditions sufficient to react essentially all the propylene to produce product comprising isopropylbenzene, polyisopropylbenzene and benzene, (c) introducing into the transalkylation zone containing a transalkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising the product of step (b), additional polyisopropylbenzene, and optionally additional benzene, wherein the molar ratio of benzene to polyisopropylbenzene is from about 0.2:1 to about 20:1, (d) contacting the reaction mixture of step (a) with the transalkylation catalyst under reaction conditions sufficient to react at least part of the benzene and polyisopropylbenzene to isopropylbenzene to produce product comprising isopropylbenzene, polyisopropylbenzene and benzene, and (e) introducing into a separation zone the product from step (d), whereby isopropylbenzene, polyisopropylbenzene and benzene are separated from each other, the isopropylbenzene is recovered as isopropylbenzene product, the benzene is added to the step (a) reaction mixture and the polyisopropylbenzene is added to the step (c) reaction mixture. ### Claim 7 (depends on 6) The process of claim 6 wherein the reaction of step (b) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 8 (depends on 7) The process of claim 7 wherein the reaction of step (d) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 9 (depends on 6) The process of claim 6 wherein said alkylation zone and transalkylation zone are combined in the same reactor. ### Claim 10 In a process for producing an alkylbenzene product selected from the group consisting of ethylbenzene and isopropylbenzene, the improvement wherein the following process steps are talcen in order: (a) introducing into an alkylation zone containing an alkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising benzene and olefin selected from the group consisting of ethylene and propylene, wherein the molar ratio of benzene to olefin is from about 1:1 to about 20:1, (b) contacting the reaction mixture of step (a) with the alkylation catalyst under reaction conditions sufficient to react essentially all the olefin to produce product comprising alkylbenzene, polyalkylbenzene and benzene, (c) introducing into a transalkylation zone containing a transalkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, 1TQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising the product of step (b), additional polyailkylbenzene, and optionally additional benzene, wherein the molar ratio of benzene to polyalkylbenzene is from about 0.2:1 to about 20:1, (d) contacting the reaction mixture of step (c) with the transalkylation catalyst under reaction conditions sufficient to react at least part of the benzene and polyalkylbenzene to allcylbcnzene to produce product comprising alkylbenzene, polyalkylbcnzenc and benzene, and (e) introducing into a separation zone the product from step (d), whereby alkylbenzene, polyalkylbenzene and benzene are separated from each other, the alkylbenzene is recovered as alkylbenzene product, the benzene is added to the step (a) reaction mixture and the polyalkylbenzene is added to the step (c) reaction mixture. ### Claim 11 (depends on 10) The process of claim 10 wherein the reaction of step (b) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of ironi about 1034 kPa to about 137S8 kPa. ### Claim 12 (depends on 11) The process of claim 11 wherein the reaction of step (d) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C arid a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 13 (depends on 10) The process of claim 10 wherein said alkylation zone and transalkylation zone are combined in the same reactor. ### Claim 14 In a process for producing an isopropylbenzene product, the improvement wherein the following process steps are taken in order: (a) introducing into an alkylation zone containing an aUcylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising benzene and propylene, wherein the molar ratio of benzene to propylene is train about 1:1 to about 20:1, (b) contacting the reaction mixture of step (a) with the alkylation catalyst under reaction conditions sufficient to react essentially all the propylene to produce product comprising isopropylbenzene, polyisopropylbenzene and benzene, (c) introducing into a transalkylation zone containing a transalkylation catalyst, said catalyst comprising at least one solid acid oxide selected from the group consisting of zeolite beta, PSH-3, ITQ-2, MCM-22, MCM-36, MCM-49 and MCM-56, a reaction mixture comprising the product of step (b), additional polyisopropylbenzene, and optionally additional benzene, wherein the molar ratio of benzene to polyisopropylbenzene is from about 0.2:1 to about 20:1, (d) contacting the reaction mixture of step (c) with the transalkylation catalyst under reaction conditions sufficient to react at least part of the benzene and palyisopropylbenzene to isopropylbenzene to produce product comprising isopropylben-sene, polyisopropylbenzene and benzene, and (e) introducing into a separation zone the product from step (d), whereby isopropylbenzene, polyisopropylbenzene and benzene are separated from each other, the isopropylbenzene is recovered as isopropylbenzene product, the benzene is added to the step (a) reaction mixture and the polyisopropylbenzene is added to the step (c) reaction mixture. ### Claim 15 (depends on 14) The process of claim 14 wherein the reaction of step (b) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 16 (depends on 15) The process of claim 15 wherein the reaction of step (d) is in at least partial liquid phase with reaction conditions including a temperature of from about 66C to about 482C and a pressure of from about 1034 kPa to about 13788 kPa. ### Claim 17 (depends on 14) The process of claim 14 wherein said alkylation zone and transalkylation zone are combined in the same reactor.