Process for producing phenol and/or cyclohexanone

Patent metadata

Field	Value
Publication number	US-9469589-B2
Application number	US-201414891177-A
Country	US
Kind code	B2
Filing date	Jun 4, 2014
Priority date	Jun 30, 2011
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

In a process for producing phenol and/or cyclohexanone, cyclohexylbenzene is contacted with an oxygen-containing gas in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide. At least a portion of the oxidation effluent is then subjected to a concentrating step to produce a cleavage feed having a higher concentration of cyclohexylbenzene hydroperoxide than the oxidation effluent. A cleavage reaction mixture comprising the cleavage feed is then contacted with a solid acid catalyst in a cleavage reaction zone under conditions effective to produce a cleavage product comprising phenol and cyclohexanone.

First claim

The invention claimed is:

1. A process for producing phenol, the process comprising:
(a) contacting cyclohexylbenzene with an oxygen-containing gas in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide at a first concentration Con1 and residual cyclohexylbenzene;
(b) concentrating at least a portion of the oxidation effluent to produce a cleavage feed comprising cyclohexylbenzene hydroperoxide at a second concentration Con2, where Con2>Con1; and
(c) contacting a cleavage reaction mixture formed from the cleavage feed with a solid acid catalyst in a cleavage reaction zone under conditions effective to produce a cleavage product comprising phenol and cyclohexanone;
(d) dividing the cleavage product into a first fraction and a second fraction, each comprising phenol and cyclohexanone;
(e) supplying a polar solvent comprising water to the second fraction to form a combined recycle stream; and
(f) providing the combined recycle stream to the cleavage reaction zone.

2. The process of claim 1 , wherein the concentrating step (b) comprises distillation to remove at least a portion of the cyclohexylbenzene in the oxidation effluent.

3. The process of claim 1 , wherein Con2−Con1>10 wt %.

4. The process of claim 1 , wherein Con2−Con1>20 wt %.

5. The process of claim 1 , wherein Con1 is in a range from 10 wt % to 30 wt % and Con2 is in a range from 30 wt % to 80 wt %.

6. The process of claim 1 , wherein Con1 is in a range from 15 wt % to 25 wt % and Con2 is in a range from 40 wt % to 60 wt %.

7. The process of claim 1 , wherein the weight ratio of the first fraction to the second fraction is in a range from 1 to 50.

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

9. The process of claim 8 , wherein the acidic molecular sieve comprises an aluminosilicate zeolite.

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

11. The process of claim 1 , further comprising:
(g) regenerating at least a portion of the solid acid catalyst.

12. A 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 an oxygen-containing gas in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide at a first concentration Con1 and residual cyclohexylbenzene;
(c) concentrating at least a portion of the oxidation effluent to produce a cleavage feed comprising cyclohexylbenzene hydroperoxide at a second concentration Con2, where Con2>Con1; and
(d) contacting a cleavage reaction mixture formed from the cleavage feed with a solid acid catalyst in a cleavage reaction zone under conditions effective to produce a cleavage product comprising phenol and cyclohexanone;
(e) dividing the cleavage product into a first fraction and a second fraction, each comprising phenol and cyclohexanone;
(f) supplying a polar solvent comprising water to the second fraction to form a combined recycle stream; and
(g) providing the combined recycle stream to the cleavage reaction zone.

13. The process of claim 12 , wherein the concentrating step (b) comprises distillation to remove at least a portion of the residual cyclohexylbenzene in the oxidation effluent.

14. The process of claim 12 , wherein Con2−Con1>10 wt %.

15. The process of claim 12 , wherein Con2−Con1>20 wt %.

16. The process of claim 12 , wherein Con1 is in a range from 10 wt % to 30 wt %, and Con2 is in a range from 30 wt % to 80 wt %.

17. The process of claim 12 , wherein Con1 is in a range from 15 wt % to 25 wt %, and Con2 is in a range from 40 wt % to 60 wt %.

18. The process of claim 12 , wherein the weight ratio of the first fraction to the second fraction is from 1 to 50.

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

20. The process of claim 19 , wherein the acidic molecular sieve comprises an aluminosilicate zeolite.

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

22. The process of claim 12 , further comprising:
(e) regenerating at least a portion of the solid acid catalyst.

Assignees

• Exxonmobile Chemical Patents Inc
• Exxonmobil Chemical Patents Inc

Inventors

• Nair Hari
• Becker Christopher L
• Davis Jason D
• Smith Charles Morris

Classifications

• C07C409/14

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

• C07C37/08

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

• C07C2/74

  by addition with simultaneous hydrogenation · CPC title

• C07C39/04

  Phenol · CPC title

• C07C13/28

  Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof · CPC title