Iridium-containing catalysts, their production and use

• US 9,382,171 B2
• Filed: 07/21/2014
• Issued: 07/05/2016
• 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.
• Primary Examiner(s): Bullock, In Suk
• Assistant Examiner(s): LOUIE, PHILIP Y
• Application Number:
  US14/336,312
• Publication Number:
  US 20140330058A1
• Time in Patent Office: 715 Days
• Field of Search: 585/251, 585/252, 585/315, 585316-320, 585/323, 585/700, 585/940
• US Class Current: 1/1
• 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- o 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. 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, methylcyclopentane, 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) contacting at least a portion of the C₆-rich stream with a first catalyst comprising finely dispersed iridium particles on the silica-containing support under conditions to produce a first reaction product stream comprising at least one paraffin, wherein a method for producing the first catalyst comprises;

a) treating a silica-containing support with an iridium compound and an organic compound selected from the group consisting of amino acids and hydroxyalkylamines 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 400°

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

c) heating the treated support 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 finely dispersed iridium particles on the silica-containing support;

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

(v) separating at least a portion of the second reaction product stream into a benzene recycle stream and a paraffin-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).

2. The process of claim 1, 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.

3. The process of claim 1, wherein the partially decomposed organic iridium complex exhibits one or more infra-red absorption bands between 2100-2200 cm⁻

1 that are not present in the organic complex before partial decomposition.

4. The process of claim 1, wherein the organic compound 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.

5. The process of claim 1, wherein the organic compound comprises tri-ethanolamine.

6. The process of claim 1, wherein the organic compound comprises arginine.