# US 9,434,661 B2 · Phenol removal in paraxylene recovery process > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,434,661 B2 - Document ID: US9434661B2 - Status: Granted - Kind: B2 - Application number: 14/642,000 - Filed: 2015-03-09 - Published: 2015-10-22 - Granted: 2016-09-06 - Earliest claimed: 2012-05-31 - Assignees: ExxonMobil Chemical Patents Inc. - Applicants: ExxonMobil Chemical Patents Inc. - Inventors: John Di-Yi Ou; Glenn A. Heeter; Shifang L. Luo; Indulis J. Eilands; Jeevan S. Abichandani; Allen S. Gawlik; Mark W. Nash; Terrance C. Osby; Robert G. Tinger - Web page: https://patentgrep.com/patent/US9434661B2 ## CPC - C07C 2/864: {the non-hydrocarbon is an alcohol} - B01J 19/24: Stationary reactors without moving elements inside (B01J19/08, B01J19/26 take precedence; with stationary particles B01J8/02) - B01J 19/245: {placed in series} - C07C 2/865: {the non-hydrocarbon is an ether} - C07C 5/2729: {Changing the branching point of an open chain or the point of substitution on a ring} - C07C 7/12: by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers - C07C 7/13: by molecular-sieve technique - C07C 7/14: by crystallisation; Purification or separation of the crystals - B01J 2219/24: Stationary reactors without moving elements inside - C07C 2529/85: Silicoaluminophosphates (SAPO compounds) - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS ## Abstract The invention is directed to purification of an aromatic hydrocarbon stream including selective removal of phenol from a process stream comprising aromatic hydrocarbon mixtures, especially aromatic hydrocarbon mixtures that contain higher-than-equilibrium paraxylene, by contact with suitable adsorbents, to provide a product stream having lower concentration of phenol than said process stream. ## Claims ### Claim 1 A process for the production of paraxylene comprising: (a) reacting toluene and/or benzene with an alkylating agent selected from methanol, dimethylether (DME), and mixtures thereof, in the presence of a catalyst comprising a porous crystalline material having a Diffusion Parameter for 2,2 dimethylbutane of about 0.1-15 sec−1 when measured at a temperature of 120° C. and a 2,2 dimethylbutane pressure of 60 torr (8 kPa), wherein said porous crystalline material has undergone prior treatment with steam at a temperature of at least 950° C. for between about 10 minutes and about 100 hours to adjust the Diffusion Parameter of said material to about 0.1-15 sec−1, under appropriate conditions to produce an aromatic hydrocarbon stream comprising paraxylene and phenolic impurities; and (b) contacting said aromatic hydrocarbon stream with a suitable adsorbent to remove the phenolic impurities selectively, so as to provide a product stream having lower concentration of phenolic impurities than said aromatic hydrocarbon stream, wherein the amount of phenolic impurities removed from said aromatic hydrocarbon stream is greater than the amount of benzene produced or paraxylene isomerized by said contact, and wherein said adsorbent is selected from alumina, silica, molecular sieves, basic organic resins, and mixtures thereof. ### Claim 2 (depends on 1) The process according to claim 1, wherein said product stream comprises less than 10 ppm wt of phenolic impurities. ### Claim 3 (depends on 1) The process according to claim 1, wherein said product stream comprises less than 1.0 ppm wt of phenolic impurities. ### Claim 4 (depends on 1) The process according to claim 1, wherein the phenolic impurities include phenol, methyl phenols and dimethyl phenols. ### Claim 5 (depends on 1) The process of claim 1, wherein said Diffusion Parameter of said porous crystalline material is about 0.5-10 sec−1. ### Claim 6 (depends on 1) The process of claim 1, wherein said porous crystalline material has undergone prior treatment with steam at a temperature of at least 1000° C. for between about 10 minutes and about 100 hours. ### Claim 7 (depends on 6) The process of claim 6, wherein said treatment with steam reduces the pore volume of the catalyst to not less than 50% of that of the pore volume of the catalyst before said treatment with steam. ### Claim 8 (depends on 1) The process of claim 1, wherein the catalyst contains at least one oxide modifier selected from the group consisting of oxides of elements of Groups IIA, IIIA, IIIB, IVA, IVB, VA and VIA of the Periodic Table. ### Claim 9 (depends on 1) The process of claim 1, wherein the catalyst contains at least one oxide modifier selected from the group consisting of oxides of boron, magnesium, calcium, lanthanum and phosphorus. ### Claim 10 (depends on 9) The process of claim 9, wherein the catalyst contains about 0.1 to about 10 wt % of the oxide modifier based on the elemental modifier. ### Claim 11 (depends on 1) The process of claim 1, wherein the catalyst has an average particle size of about 20 to 200 microns. ### Claim 12 (depends on 1) The process of claim 1, wherein the catalyst comprises a phosphorus-containing ZSM-5 catalyst. ### Claim 13 (depends on 1) The process according to claim 1, wherein said aromatic hydrocarbon stream further comprises styrene and said process includes removing at least a portion of said styrene. ### Claim 14 (depends on 1) The process according to claim 1, further comprising: (c) recovering the paraxylene via adsorptive separation or crystallization to produce a paraxylene-enriched stream and a paraxylene-depleted stream. ### Claim 15 (depends on 14) The process according to claim 14, further comprising: (d) isomerizing the paraxylene-depleted stream in the vapor phase, liquid phase, or a combination thereof in series or parallel, to produce equilibrium xylenes. ### Claim 16 (depends on 1) The process according to claim 1, further including a step of regenerating said adsorbent. ### Claim 17 (depends on 16) The process according to claim 16, wherein said step of regenerating said adsorbent is selected from at least one of: (1) purge with mixture(s) of at least one inert gas and at least one organic solvent selected from aromatics, alcohols, ketones, water, CO2, CS2, and mixtures thereof, at a temperature >20° C.; (3) purge with an organic solvent selected from at least one of aromatics, alcohols, ketones, water, CO2, CS2, and mixtures thereof at a temperature >20° C., followed by an inert gas purge at a temperatures >100° C.; (4) purge with mixture(s) of at least one organic solvent and at least one inorganic solvent at a temperature >25° C., followed by an inert gas purge at a temperature >150° C.; and (5) purge with air, mixture of oxygen and nitrogen, steam, or mixture thereof at a temperature >150° C.