Process for producing phenol and/or cyclohexanone

Patent metadata

Field	Value
Publication number	US-9656934-B2
Application number	US-201414892513-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Jun 28, 2013
Publication date	May 23, 2017
Grant date	May 23, 2017

Abstract

In a process for producing phenol, a cleavage feed comprising cyclohexylbenzene hydroperoxide is supplied to a cleavage reaction zone and a cleavage reaction mixture comprising the cleavage feed is contacted in the cleavage reaction zone with a solid acid catalyst under conditions effective to produce a cleavage effluent comprising phenol and cyclohexanone. The cleavage effluent is then divided into at least a cleavage product and a cleavage recycle and the cleavage recycle and a polar solvent is supplied to the cleavage reaction zone to produce the cleavage reaction mixture with the cleavage feed. Preferably, the polar solvent is combined with the cleavage recycle before being charged into the cleavage reaction zone.

First claim

The invention claimed is:

1. A continuous process for producing phenol, the process comprising:
(a) continuously supplying a cleavage feed comprising cyclohexylbenzene hydroperoxide to a cleavage reaction zone;
(b) continuously contacting a cleavage reaction mixture comprising the cleavage feed in the cleavage reaction zone with a solid acid catalyst under conditions effective to continuously produce a cleavage effluent comprising phenol and cyclohexanone, wherein the cleavage reaction mixture further comprises from 20 wt % to 40 wt % phenol;
(c) dividing the cleavage effluent into at least a cleavage product and a cleavage recycle; and
(d) supplying the cleavage recycle and a polar solvent to the cleavage reaction zone to produce the cleavage reaction mixture with the cleavage feed;
wherein at least part of the polar solvent is combined with the cleavage recycle to produce a combined stream which is continuously supplied to the cleavage reaction zone in (d).

2. The process of claim 1 , wherein the polar solvent is supplied to the cleavage reaction zone in (d) in an amount from 100 ppm to 10% by weight of the cleavage reaction mixture.

3. The process of claim 2 , wherein the polar solvent is supplied to the cleavage reaction zone in (d) in an amount from 1000 ppm to 5% by weight of the cleavage reaction mixture.

4. The process of claim 1 , wherein the polar solvent is water.

5. The process of claim 1 , wherein the cleavage effluent comprises unreacted cyclohexylbenzene hydroperoxide.

6. The process of claim 1 , wherein the solid acid catalyst comprises an acidic molecular sieve.

7. The process of claim 6 , wherein the acidic molecular sieve comprises an aluminosilicate zeolite.

8. The process of claim 6 , wherein the acidic molecular sieve comprises at least one of zeolite beta, faujasite, ZSM-12, mordenite and an MCM-22 family molecular sieve.

9. The process of claim 6 , wherein the acidic molecular sieve comprises faujasite.

10. The process of claim 6 , wherein the acidic molecular sieve comprises faujasite having a unit cell size of less than 24.50 {acute over (Å)}.

11. The process of claim 1 , wherein the conditions in (b) include a temperature from about 20° C. to about 200° C. and an absolute pressure from about 100 kPa to about 2000 kPa.

12. A continuous process for producing phenol, the process comprising:
(a) hydroalkylating benzene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising cyclohexylbenzene;
(b) contacting at least a portion of the cyclohexylbenzene from the hydroalkylation reaction product with oxygen in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation product comprising cyclohexylbenzene hydroperoxide;
(c) supplying at least a portion of the oxidation product comprising cyclohexylbenzene hydroperoxide to a cleavage reaction zone;
(d) continuously contacting a cleavage reaction mixture comprising the said oxidation product portion in the cleavage reaction zone with a solid acid catalyst under conditions effective to continuously produce a cleavage effluent comprising phenol and cyclohexanone, wherein the cleavage reaction mixture further comprises from 20 wt % to 40 wt % phenol;
(e) dividing the cleavage effluent into at least a cleavage product and a cleavage recycle; and
(f) supplying the cleavage recycle and a polar solvent to the cleavage reaction zone to produce the cleavage reaction mixture with said oxidation product portion;
wherein at least part of the polar solvent is combined with the cleavage recycle to produce a combined stream which is continuously supplied to the cleavage reaction zone in (f).

13. The process of claim 12 , wherein the polar solvent is supplied to the cleavage reaction zone in (f) in an amount such that the cleavage reaction mixture comprises from 100 ppm to 10% by weight of the polar solvent.

14. The process of claim 12 , wherein the polar solvent is supplied to the cleavage reaction zone in (f) in an amount such that the cleavage reaction mixture comprises from 1000 ppm to 5% by weight of the polar solvent.

15. The process of claim 12 , wherein the polar solvent is water.

16. The process of claim 12 , wherein the cleavage effluent comprises unreacted cyclohexylbenzene hydroperoxide.

17. The process of claim 12 , wherein the solid acid catalyst comprises an acidic molecular sieve.

18. The process of claim 17 , wherein the acidic molecular sieve comprises an aluminosilicate zeolite.

19. The process of claim 17 , wherein the acidic molecular sieve comprises at least one of zeolite beta, faujasite, ZSM-12, mordenite and an MCM-22 family molecular sieve.

20. The process of claim 17 , wherein the acidic molecular sieve comprises faujasite.

21. The process of claim 17 , wherein the acidic molecular sieve comprises faujasite having a unit cell size of less than 24.50 {acute over (Å)}.

22. The process of claim 12 , wherein the conditions in (b) include a temperature from about 20° C. to about 200° C. and a pressure from about 100 kPa to about 2000 kPa.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Nair Hari
• Becker Christopher L
• Nimmo Karen S
• Lattner James R
• Benitez Francisco M
• Smith Charles Morris

Classifications

• C07C45/53

  of hydroperoxides · CPC title

• C07C13/28

  Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof · CPC title

• C07C2/74

  by addition with simultaneous hydrogenation · CPC title

• C07C39/04

  Phenol · CPC title

• C07C409/14

  the carbon atom belonging to a ring other than a six-membered aromatic ring · CPC title