Iridium-Containing Catalysts, Their Production and Use

• US 20140330058A1
• Filed: 07/21/2014
• Published: 11/06/2014
• Est. Priority Date: 02/05/2010
• Status: Active Grant

• Current Assignee: ExxonMobil Chemical Patents Inc. (Exxon Mobil Corporation)
• Original Assignee: ExxonMobil Chemical Patents Inc. (Exxon Mobil Corporation)
• Inventors: Soled, Stuart L., Miseo, Sabato, Baumgartner, Joseph E., Kliewer, Christine E., Cheng, Jane C.
• Granted Patent: US 9,382,171 B2
• Time in Patent Office: Days
• US Class Current: 585/251
• CPC Class Codes: B01J 23/468 Iridium
• CPC Class Codes: B01J 37/0203 the impregnation liquid containing organic compounds
• CPC Class Codes: B01J 37/08 Heat treatment B01J37/0009, B01J37/0018 take precedence
• CPC Class Codes: C07C 11/02 Alkenes
• CPC Class Codes: C07C 13/28 Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
• CPC Class Codes: C07C 2/74 by addition with simultaneous hydrogenation
• CPC Class Codes: C07C 2521/08 Silica
• CPC Class Codes: C07C 2531/08 Ion-exchange resins
• CPC Class Codes: C07C 2601/12 with a six-membered ring
• CPC Class Codes: C07C 5/00 Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
• CPC Class Codes: C07C 5/31 changing the number of rings
• CPC Class Codes: C07C 9/00 Aliphatic saturated hydrocarbons
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

A process is described for producing a catalyst composition comprising an iridium component dispersed on a support. In the process, silica-containing support is treated with an iridium compound and an organic compound comprising an amino group to form an organic iridium complex on the support. The treated support is then heated in an oxidizing atmosphere at a temperature of about 325° C. to about 475° C. to partially decompose the organic metal complex on the support. The treated support is then heated in a reducing atmosphere at a temperature of about 350° C. to about 500° C. to convert the partially decomposed organic iridium complex into the desired iridium component.

Claims

1-13. -13. (canceled)

25. A process for producing cyclohexylbenzene, the process comprising:

(i) contacting benzene and hydrogen in the presence of a hydroalkylation catalyst under hydroalkylation conditions effective to form a hydroalkylation reaction product stream comprising cyclohexylbenzene, cyclohexane, methyl cyclopentane, and benzene;

(ii) separating at least a portion of the hydroalkylation reaction product stream into a C₆-rich stream comprising benzene, cyclohexane, and methylcyclopentane and a cyclohexylbenzene-rich stream;

(iii) producing a first reaction product stream comprising the step of contacting at least a portion of the C₆-rich stream with a first catalyst comprising at least one support and at least one metal component and the contacting being conducted under conditions to convert at least a portion of the methylcyclopentane to at least one paraffin wherein the first catalyst is produced by a method comprising;

a) treating a silica-containing support with an iridium compound and an organic compound comprising an amino group to form a treated support comprising an organic iridium complex on the support;

b) heating the treated support in an oxidizing atmosphere at a temperature of about 325°

C. to about 450°

C. to partially decompose the organic iridium complex on the support to form a partially decomposed organic iridium complex; and

c) heating the treated support in an reducing atmosphere at a temperature of about 350°

C. to about 500°

C. to convert the partially decomposed organic iridium complex into the iridium component;

(iv) producing a second reaction product stream comprising the step of contacting at least a portion of the first reaction product stream with a second catalyst comprising at least one support and at least one metal component and under conditions effective to convert at least a portion of the cyclohexane to benzene;

(v) separating at least a portion of the second reaction product stream produced in producing step (iv) into a benzene recycle stream and a paraffins-rich stream comprising 2-methylpentane and 3-methylpentane; and

(vi) recycling at least a portion of the benzene recycle stream to the contacting step (i).

14. The process of claim 25, wherein the at least one organic compound is selected from an (i) amino acids;

and (ii) compounds comprising an amino group and an alcohol group.

15. The process of claim 25, wherein the partially decomposed organic iridium complex retains between 10 and 95% by weight of the dry weight attributed to the organic iridium complex prior to partial decomposition.

16. The process of claim 25, wherein the cyclic aliphatic hydrocarbon is methylcyclopentane.

18. The process of claim 25, wherein the organic compound comprises an aliphatic amine containing one or more hydroxyl groups.

19. The process of claim 25, wherein the organic compound comprises a hydroxyalkylamine.

20. The process of claim 19, wherein the hydroxyalkylamine comprises one or more of:

methanolamine, di-methanolamine, tri-methanolamine, ethanolamine, di-ethanolamine, tri-ethanolamine, butanolamine, di-butanolamine, tri-butanolamine, propanolamine, di-propanolamine, dimethylethanolamine, di-isopropylethanolamine, methyldiethanolamine, dimethylamino-2-propanol, and tri-propanolamine.

21. The process of claim 25, wherein the organic compound comprises tri-ethanolamine.

22. The process of claim 25, wherein the organic compound comprises an amino acid.

23. The process of claim 25, wherein the amino acid comprises arginine.

24. The process of claim 25, wherein the heating step (b) comprises heating the treated support to a temperature of about 375°

C. to about 425°

C.