Phenol removal in paraxylene recovery process

Patent metadata

Field	Value
Publication number	US-9012711-B2
Application number	US-201313875402-A
Country	US
Kind code	B2
Filing date	May 2, 2013
Priority date	May 31, 2012
Publication date	Apr 21, 2015
Grant date	Apr 21, 2015

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.

First claim

What is claimed is:

1. A process for the purification of an aromatic hydrocarbon stream containing phenol, comprising contact of said aromatic hydrocarbon stream with an adsorbent selective for the absorption of phenol, to provide a product stream having lower concentration of phenol than said process stream, wherein the amount of phenol removed from said process stream is greater than the amount of benzene produced or paraxylene isomerized by said contact, and wherein said aromatic hydrocarbon stream comprises effluent downstream of an alkylation process comprising the reaction of an alkylating agent selected from methanol, DME, and mixtures thereof, with benzene and/or toluene in the presence of a suitable alkylation catalyst under appropriate conditions to provide said aromatic hydrocarbon stream wherein said adsorbent is selected from alumina, silica, molecular sieves, basic organic resins, and mixtures thereof.

2. The process according to claim 1 , said process including the production of paraxylene selectively, and comprising:
(i) reacting of toluene and/or benzene with an alkylating agent selected from methanol, dimethylether (DME), and mixtures thereof, in the presence of a suitable catalyst under appropriate conditions to produce an aromatic hydrocarbon stream comprising paraxylene in higher than equilibrium amounts; and
(ii) contacting said aromatic hydrocarbon stream with a suitable adsorbent to remove phenol selectively, so as to provide a product stream having lower concentration of phenol than said process stream.

3. The process according to claim 1 , wherein said product stream comprises less than 10 ppm wt of phenol.

4. The process according to claim 1 , wherein said product stream comprises less than 1.0 ppm wt of phenol.

5. The process according to claim 1 , further including a step of regenerating said adsorbent.

6. The process according to claim 5 , 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, CO 2 , CS 2 , and mixtures thereof, at a temperature >20° C.; (3) purge with an organic solvent selected from at least one of aromatics, alcohols, ketones, water, CO 2 , CS 2 , 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.

7. The process according to claim 1 , wherein said aromatic hydrocarbon stream further comprises styrene and said process includes a step of the removal of at least a portion of said styrene.

8. The process according to claim 1 , further including a step of recovery of paraxylene.

9. The process according to claim 8 , wherein said step of recovery of paraxylene comprises a step of crystallization and/or selective adsorption of paraxylene.

10. The process according to claim 9 , wherein said step of recovery of paraxylene is downstream of said contact of said aromatic hydrocarbon stream with an adsorbent selective for the absorption of phenol relative to xylenes, and comprises the step of selective removal of paraxylene to provide a paraxylene-enriched aromatic hydrocarbon stream and a paraxylene-depleted aromatic hydrocarbon stream.

11. The process according to claim 1 , further including a step of isomerization.

12. The process according to claim 1 , wherein at least one step in said process is in the presence of hydrogen.

13. The process according to claim 1 , including the reaction of an alkylating agent selected from methanol, DME, and mixtures thereof, with benzene and/or toluene in the presence of an acid active catalyst, comprising ZSM-5.

14. The process according to claim 13 , wherein the catalyst comprises a phosphorus-containing ZSM-5 catalyst that has been steamed.

Assignees

• Exxonmobil Chem Patents Inc

Inventors

• Ou John Di-Yi
• Heeter Glenn A
• Luo Shifang L
• Eilands Indulis J
• Abichandani Jeevan S
• Gawlik Allen Scott
• Nash Mark W
• Osby Terrance C
• Tinger Robert G

Classifications

• C07C7/13 Primary

  by molecular-sieve technique · CPC title

• C07C7/12 Primary

  by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers · CPC title

• C07C2/864 Primary

  the non-hydrocarbon is an alcohol · CPC title

• C07C37/68 Primary

  Purification; separation; Use of additives, e.g. for stabilisation {(C07C37/004 and C07C37/005 take precedence)} · CPC title

• C07C2/865

  the non-hydrocarbon is an ether · CPC title