Dehydrogenation process

• US 9,024,078 B2
• Filed: 12/17/2010
• Issued: 05/05/2015
• 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., Miseo, Sabato, Lattner, James R., Chen, Tan-Jen, Helton, Terry E., Xu, Teng
• Primary Examiner(s): Zucker, Paul A
• Assistant Examiner(s): LUDERER, MARK R
• Application Number:
  US13/515,104
• Publication Number:
  US 20120302798A1
• Time in Patent Office: 1,600 Days
• Field of Search: 568/798, 585/379
• US Class Current: 568/798
• CPC Class Codes: B01J 23/58 with alkali- or alkaline earth metals
• CPC Class Codes: B01J 35/615 100-500 m2/g
• CPC Class Codes: B01J 35/647 2-50 nm
• CPC Class Codes: B01J 37/0009 Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
• CPC Class Codes: B01J 37/0203 the impregnation liquid containing organic compounds
• CPC Class Codes: C07C 15/04 Benzene
• CPC Class Codes: C07C 2521/08 Silica
• CPC Class Codes: C07C 2523/42 Platinum
• CPC Class Codes: C07C 2523/58 with alkali- or alkaline earth metals or beryllium
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 37/07 with simultaneous reduction of C=O group in that ring
• 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: C07C 5/367 Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
• CPC Class Codes: Y02P 20/52 using catalysts, e.g. selective catalysts

Abstract

A dehydrogenation process for the dehydrogenation of at least one dehydrogenatable hydrocarbon, the process comprising contacting a feed comprising the at least one dehydrogenatable hydrocarbon under dehydrogenation conditions with a catalyst composition comprising a support and at least one dehydrogenation component wherein said conditions include a temperature of from 400° C. to 750° C. and a pressure of at least 50 psig (345 kPag).

Claims

1. A process for the dehydrogenation of at least one dehydrogenatable hydrocarbon, the process comprising contacting a feed comprising the at least one dehydrogenatable hydrocarbon under dehydrogenation conditions with a catalyst composition free of germanium comprising a support and a dehydrogenation component comprising at least one metal component selected from platinum and palladium, wherein said conditions include a temperature of from 400°

C. to 750°

C. and a pressure of at least 50 psig, the catalyst composition has an oxygen chemisorption of greater than 50%.

2. The process of claim 1, wherein the at least one dehydrogenatable hydrocarbon is an alicyclic compound.

3. The process of claim 1, wherein the at least one dehydrogenatable hydrocarbon is cyclohexanone.

4. The process of claim 1, wherein said temperature is at least 450°

C.

5. The process of claim 1, wherein said temperature is at least 460°

C.

6. The process of claim 1, wherein said temperature is at least 470°

C.

7. The process of claim 1, wherein said temperature is at least 500°

C.

8. The process of claim 1, wherein said temperature is at least 550°

C.

9. The process of claim 1, wherein said pressure is at least 75 psig.

10. The process of claim 1, wherein said pressure is at least 90 psig.

11. The process of claim 1, wherein the catalyst composition has an oxygen chemisorption of greater than 70%.

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

13. The process of claim 1, wherein the support comprises silica.

14. The process of claim 1, wherein the dehydrogenation component is a metal component comprising platinum.

15. The process of claim 1, wherein the catalyst composition is capable of dehydrogenating the dehydrogenatable hydrocarbon at a conversion of 95% or more.

16. The process of claim 1, wherein said conditions further include introducing hydrogen to the process.

17. The process of claim 1, wherein said catalyst composition further comprises an inorganic base component comprising at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements wherein said at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements is present in an amount of at least 0.1 wt %.

18. The process of claim 17, wherein the inorganic base component is at least one metal component selected from potassium, cesium and rubidium.

19. The process of claim 17, wherein the inorganic base component is a metal component comprising potassium.

20. The process of claim 1, wherein said catalyst composition comprises:

(i) a support;

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

(iii) a inorganic base component comprising at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements;

wherein said at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements is present in an amount of at least 0.1 wt %.

21. A process for producing phenol, the process comprising:

(a) oxidizing cyclohexylbenzene to produce cyclohexylbenzene hydroperoxide;

(b) converting at least a portion of cyclohexylbenzene hydroperoxide from (a) to produce an effluent stream comprising phenol and cyclohexanone; and

(c) contacting at least a portion of said effluent stream with a catalyst composition free of germanium comprising a support, a dehydrogenation component comprising at least one metal component comprising at least one metal component selected from platinum and palladium and an inorganic base component comprising at least one metal component selected from Group 1 and Group 2 of the Periodic Table of Elements under dehydrogenation conditions effective to convert at least at least a portion of the cyclohexanone in said feed into phenol and hydrogen;

wherein said dehydrogenation conditions include a temperature of at least 450°

C. and a pressure of at least 90 psig, the catalyst composition has an oxygen chemisorption of greater than 50%.

22. The process of claim 21, wherein the at least a portion of said effluent stream in said contacting (c) has the same composition as the effluent stream produced in said converting (b).