Process for producing cyclohexanone

• US 8,222,459 B2
• Filed: 02/19/2009
• Issued: 07/17/2012
• Est. Priority Date: 06/13/1997
• 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., Buchanan, John S., Lattner, James R., Mizrahi, Sadi
• Primary Examiner(s): WITHERSPOON, SIKARL A
• Application Number:
  US12/933,700
• Publication Number:
  US 20110021844A1
• Time in Patent Office: 1,244 Days
• Field of Search: 568/346, 568/361
• US Class Current: 568/346
• 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 45/006 by hydrogenation of aromatic hydroxy compounds
• CPC Class Codes: C07C 45/53 of hydroperoxides
• CPC Class Codes: C07C 49/403 of a six-membered ring

Abstract

In a process for producing cyclohexanone, cyclohexylbenzene is oxidized to produce cyclohexylbenzene hydroperoxide and then the resultant cyclohexylbenzene hydroperoxide is cleaved to produce an effluent stream comprising phenol and cyclohexanone. At least a portion of the effluent stream is then fed to at least one hydrogenation reaction zone, where the effluent stream portion is contacted with hydrogen in the presence of a hydrogenation catalyst under conditions effective to convert at least part of the phenol in the effluent portion into cyclohexanone.

Claims

1. A process for producing cyclohexanone, the process comprising:

(a) oxidizing cyclohexylbenzene to produce cyclohexylbenzene hydroperoxide;

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

(c) feeding at least a portion of the effluent stream comprising phenol and cyclohexanone to at least one hydrogenation reaction zone; and

(d) contacting the effluent stream portion with hydrogen in the presence of a hydrogenation catalyst in the hydrogenation reaction zone under conditions effective to convert at least part of the phenol in the effluent portion into cyclohexanone.

2. The process of claim 1, wherein the effluent stream portion fed to the hydrogenation reaction zone has the same composition as the effluent stream produced by the converting (b).

3. The process of claim 1 and further including subjecting the effluent stream produced by the converting (b) to at least one separation step such that the effluent stream portion fed to the hydrogenation reaction zone contains less cyclohexanone than the effluent stream produced by the converting (b).

4. The process of claim 3, wherein the effluent stream portion fed to the hydrogenation reaction zone contains less than 50 wt % cyclohexanone.

5. The process of claim 1, wherein the conditions in (d) comprise a temperature of from 20°

C. to 250°

C. and/or a pressure of from 101 kPa to 10,000 kPa and/or a hydrogen to phenol molar ratio of 1;

1 to 100;

1.

6. The process of claim 1, wherein the hydrogenation catalyst comprises platinum and/or palladium.

7. The process of claim 1 which further comprises a step of contacting benzene and hydrogen with a hydroalkylation catalyst under hydroalkylation conditions to produce the cyclohexylbenzene for oxidizing in (a).

8. The process of claim 7, wherein said the hydroalkylation catalyst comprises a molecular sieve of the MCM-22 family.

9. The process of claim 7, wherein the hydroalkylation conditions include a temperature of from 100°

C. to 400°

C. and/or a pressure of from 100 to 7,000 kPa and/or a molar ratio of hydrogen to benzene of from 0.15;

1 to 15;

1.

10. The process of claim 1, wherein at least a portion of the cyclohexanone product is contacted with a dehydrogenation catalyst under dehydrogenation conditions to convert the cyclohexanone to phenol.

11. A process for producing cyclohexanone, the process comprising:

(a) oxidizing cyclohexylbenzene to produce cyclohexylbenzene hydroperoxide;

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

(c) feeding at least a portion of the effluent stream comprising phenol and cyclohexanone to at least one hydrogenation reaction zone; and

(d) contacting the effluent stream portion with hydrogen in the presence of a hydrogenation catalyst in the hydrogenation reaction zone under conditions effective to convert at least part of the phenol in the effluent portion into cyclohexanone wherein the effluent stream produced by the converting (b) is subjected to at least one separation step such that the effluent stream portion fed to the hydrogenation reaction zone contains less cyclohexanone than the effluent stream produced by the converting (b).

12. A process for producing cyclohexanone, the process comprising:

(a) oxidizing cyclohexylbenzene to produce cyclohexylbenzene hydroperoxide;

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

(c) feeding at least a portion of the effluent stream comprising phenol and cyclohexanone to at least one hydrogenation reaction zone; and

(d) contacting the effluent stream portion with hydrogen in the presence of a hydrogenation catalyst in the hydrogenation reaction zone under conditions effective to convert at least part of the phenol in the effluent portion into cyclohexanone wherein the effluent stream portion fed to the hydrogenation reaction zone has the same composition as the effluent stream produced by the converting (b).