Process for producing phenol

Patent metadata

Field	Value
Publication number	US-9061975-B2
Application number	US-201113983989-A
Country	US
Kind code	B2
Filing date	Nov 21, 2011
Priority date	Feb 28, 2011
Publication date	Jun 23, 2015
Grant date	Jun 23, 2015

Abstract

In a process for producing phenol, cyclohexylbenzene is oxidized to form a first reaction product comprising cyclohexylbenzene hydroperoxide and at least a portion of the cyclohexylbenzene hydroperoxide is then cleaved to form a second reaction product comprising phenol and cyclohexanone. At least one of the first and second reaction products comprises cyclohexenone, which is hydrogenated to produce further cyclohexanone.

First claim

The invention claimed is:

1. A process for producing phenol, the process comprising:
(a) oxidizing cyclohexylbenzene to form a first reaction product comprising cyclohexylbenzene hydroperoxide; and
(b) cleaving at least a portion of the cyclohexylbenzene hydroperoxide from (a) to form a second reaction product comprising phenol and cyclohexanone,
wherein at least one of the first reaction product and the second reaction product comprises cyclohexenone and the process further comprises:
(c) hydrogenating at least a portion of the cyclohexenone to cyclohexanone.

2. The process of claim 1 , wherein at least one of the first and second reaction products comprises at least 0.01 wt % of cyclohexenone, based upon total weight of the reaction product.

3. The process of claim 1 , wherein at least one of the first and second reaction products comprises at least 0.05 wt % of cyclohexenone, based upon total weight of the reaction product.

4. The process of claim 1 , wherein the hydrogenating (c) is conducted to a degree sufficient to hydrogenate at least 70% of the cyclohexenone to cyclohexanone.

5. The process of claim 1 , wherein the hydrogenating (c) is conducted to a degree sufficient to hydrogenate at least 90% of the cyclohexenone to cyclohexanone.

6. The process of claim 1 , wherein at least one of the first and the second reaction products comprises up to 10 wt % of cyclohexenone, based upon total weight of the reaction product.

7. The process of claim 1 , wherein the hydrogenating (c) is conducted at hydrogenation conditions comprising a temperature of about 20° C. to about 150° C.

8. The process of claim 1 , wherein the hydrogenating (c) is conducted at hydrogenation conditions comprising a temperature of about 60° C. to about 100° C.

9. The process of claim 1 , wherein the hydrogenating (c) is conducted at hydrogenation conditions comprising a hydrogen partial pressure of about 0 kPag to about 2000 kPag.

10. The process of claim 1 , wherein the hydrogenating (c) is conducted at hydrogenation conditions comprising a hydrogen partial pressure of about 200 kPag to 1000 kPag.

11. The process of claim 1 , wherein the hydrogenating (c) is conducted in the presence of a hydrogenation catalyst comprising a hydrogenation component and a support.

12. The process of claim 11 , wherein the hydrogenation component comprises at least one element or compound thereof selected from Groups 6 to 10 of the Periodic Table of Elements.

13. The process of claim 11 , wherein the hydrogenation component comprises palladium or a palladium compound.

14. The process of claim 11 , wherein the hydrogenation component comprises about 0.1 wt % to about 10 wt % of the hydrogenation catalyst.

15. The process of claim 11 , wherein the hydrogenation component comprises about 0.3 wt % to about 1 wt % of the hydrogenation catalyst.

16. The process of claim 11 , wherein the support comprises at least one of aluminum oxide, silica, silicate, aluminosilicate, carbon, and a carbon nanotube.

17. The process of claim 1 , wherein at least part of the second reaction product comprising phenol, cyclohexanone, and cyclohexenone is subjected to the hydrogenating (c).

18. The process of claim 1 , wherein the second reaction product is separated into a first stream rich in cyclohexanone and cyclohexenone and a second stream rich in phenol, and at least part of the first stream is subjected to the hydrogenating (c).

19. The process of claim 1 , wherein at least part of the cyclohexylbenzene in (a) is formed by reacting benzene with hydrogen.

20. The process of claim 1 , and further comprising dehydrogenating at least a part of the cyclohexanone from the second reaction product to form phenol.

21. A process for producing phenol, the process comprising:
(a) reacting benzene with hydrogen to form cyclohexylbenzene;
(b) oxidizing at least a portion of the cyclohexylbenzene to form a first reaction product comprising cyclohexylbenzene hydroperoxide; and
(c) cleaving at least a portion of the cyclohexylbenzene hydroperoxide from (a) to form a second reaction product comprising phenol and cyclohexanone,
wherein at least one of the first and second reaction products comprises at least 0.05 wt % of cyclohexenone and the process further comprises:
(d) hydrogenating at least a portion of the cyclohexenone to cyclohexanone, wherein at least 50 wt % of the cyclohexenone is hydrogenated.

Assignees

• Becker Christopher L
• Lattner James R
• Kuechler Keith H
• Benitez Francisco M
• Smith Charles Morris
• Exxonmobil Chem Patents Inc

Inventors

• Becker Christopher L
• Lattner James R
• Kuechler Keith H
• Benitez Francisco M
• Smith Charles Morris

Classifications

• C07C2/74 Primary

  by addition with simultaneous hydrogenation · CPC title

• C07C45/517

  involving transformation of peroxy-compounds to >C = O groups · CPC title

• C07C2101/16

  Chemistry & Metallurgy · mapped topic

• C07C39/04

  Phenol · CPC title

• C07C37/08 Primary

  by decomposition of hydroperoxides, e.g. cumene hydroperoxide · CPC title