Dehydrogenation catalyst and process

• US 9,242,227 B2
• Filed: 12/17/2010
• Issued: 01/26/2016
• 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: Dakka, Jihad M., Decaul, Lorenzo C., Helton, Terry E., Xu, Teng, Wallace, Jenna L.
• Primary Examiner(s): Katakam, Sudhakar
• Assistant Examiner(s): Bakshi, Pancham
• Application Number:
  US13/515,142
• Publication Number:
  US 20120302799A1
• Time in Patent Office: 1,866 Days
• Field of Search: 568/300, 568/772, 568/799, 568/806
• US Class Current: 1/1
• CPC Class Codes: B01J 21/08 Silica
• CPC Class Codes: B01J 23/58 with alkali- or alkaline earth metals
• CPC Class Codes: B01J 37/0205 in several steps
• CPC Class Codes: B01J 37/12 Oxidising
• 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 2529/70 of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 37/06 by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
• CPC Class Codes: C07C 37/08 by decomposition of hydroperoxides, e.g. cumene hydroperoxide
• CPC Class Codes: C07C 39/04 Phenol
• CPC Class Codes: C07C 407/00 Preparation of peroxy compounds
• CPC Class Codes: C07C 409/14 the carbon atom belonging to a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 45/53 of hydroperoxides
• CPC Class Codes: C07C 49/403 of a six-membered ring
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

A catalyst composition comprises (i) a support; (ii) a dehydrogenation component comprising at least one metal or compound thereof selected from Groups 6 to 10 of the Periodic Table of Elements; and (iii) potassium or a potassium compound present in an amount of about 0.15 to about 0.6 wt % of potassium based upon the total weight of the catalyst composition, wherein the catalyst composition has an oxygen chemisorption of greater than 50%.

Claims

1. A process for the dehydrogenation of cyclohexanone to produce phenol, the process comprising contacting a feed comprising cyclohexanone under dehydrogenation conditions with catalyst composition comprising (i) a support;

(ii) a dehydrogenation component comprising at least one metal or compound thereof selected from Groups 6 to 10 of the Periodic Table of Elements; and

(iii) potassium or a potassium compound,

wherein the potassium is present in an amount of about 0.15 to about 0.6 wt % based upon the total weight of the catalyst composition,

wherein the catalyst composition is prepared by sequential impregnation with the potassium or potassium compound being applied to the support before the dehydrogenation component is applied to the support, and

wherein the catalyst composition has an oxygen chemisorption of greater than 50%.

2. The method of claim 1, wherein the potassium is present in an amount of about 0.2 to about 0.5 wt %, based upon the total weight of the catalyst composition.

3. The method of claim 1, wherein the support is selected from the group consisting of silica, a silicate, an aluminosilicate, zirconia, and carbon.

4. The method of claim 1, wherein the dehydrogenation component comprises at least one of platinum and palladium.

5. The method of claim 1, wherein the catalyst composition improves phenol selectivity relative to dehydrogenation catalysts containing greater than 0.6 wt % of potassium.

6. The method of claim 1, wherein the dehydrogenation component is present in an amount of about 0.01 to about 2 wt %, based upon the total weight of the catalyst composition.

7. The method of claim 1, wherein the dehydrogenation component is present in an amount of about 0.5 to about 1.5 wt % based upon the total weight of the catalyst composition.

8. A process for producing phenol from benzene, the process comprising:

(a) reacting benzene and hydrogen with a catalyst under hydroalkylation conditions to produce cyclohexylbenzene;

(b) oxidizing cyclohexylbenzene from (a) to produce cyclohexylbenzene hydroperoxide;

(c) converting cyclohexylbenzene hydroperoxide from (b) to produce an effluent stream comprising phenol and cyclohexanone; and

(d) contacting at least a portion of the effluent stream from (c) with a dehydrogenation catalyst comprising;

(i) a support;

(ii) a dehydrogenation component comprising at least one metal or compound thereof selected from Groups 6 to 10 of the Periodic Table of Elements; and

(iii) potassium or a potassium compound, wherein the potassium is present in an amount of about 0.15 to about 0.6 wt % based upon the total weight of the catalyst composition, wherein the dehydrogenation catalyst is prepared by sequential impregnation with the potassium or potassium compound being applied to the support before the dehydrogenation component is applied to the support, and further wherein the contacting occurs under dehydrogenation conditions effective to convert at least part of the cyclohexanone in the effluent stream into phenol and hydrogen.

9. The process of claim 8, wherein the catalyst provides a reduced selectivity to one or more of pentane, pentene and carbon monoxide relative to dehydrogenation catalysts containing greater than 0.6 wt % of potassium.