Activation and use of hydroalkylation catalysts

Patent metadata

Field	Value
Publication number	US-9555403-B2
Application number	US-201314403806-A
Country	US
Kind code	B2
Filing date	Jul 9, 2013
Priority date	Jul 24, 2012
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

A process for activating a hydroalkylation catalyst in a first state comprising an acid component and a hydrogenating metal component, including: (i) treatment at a temperature of at least 120° C. in the presence of hydrogen for a first duration to produce a catalyst in a second state having a first hydroalkylation activity; (ii) contacting the catalyst in the second state with an aromatic compound and hydrogen under a hydroalkylation condition effective to convert at least part of the aromatic compound to a cycloalkylaromatic compound and produce a catalyst in a third state; and (iii) treating the catalyst in the third state at a temperature of at least 160° C. in the presence of hydrogen but advantageously in the substantial absence of the aromatic compound for a third duration to produce an activated catalyst in a fourth state having a third hydroalkylation activity greater than the first hydroalkylation activity.

First claim

The invention claimed is:

1. A process for activating a hydroalkylation catalyst, the process comprising:
(a) providing a hydroalkylation catalyst in a first state comprising an acid component and a hydrogenating metal component;
(b) treating the catalyst in the first state at a first temperature of at least 120° C. in a first atmosphere comprising hydrogen and at most 5% by mole of an aromatic compound for a first duration to produce a catalyst in a second state having a first hydroalkylation activity HA1;
(c) contacting the catalyst in the second state with a first aromatic compound and a second atmosphere comprising hydrogen under a first hydroalkylation condition at a second temperature for a second duration effective to convert at least part of the first aromatic compound into a second aromatic compound comprising an alkyl group, and thereby obtaining a catalyst in a third state having a second hydroalkylation activity HA2, where HA2 is no lower than HA1, the second duration ranges from at least 0.5 hour to 300 hours, and the second temperature is in a range from 100° C. to 400° C.; and
(d) treating the catalyst in the third state at a third temperature of at least 160° C. in a third atmosphere comprising hydrogen and less than 30% by mole of the first aromatic compound for a third duration to produce a catalyst in a fourth state having a third hydroalkylation activity HA3, where HA3>HA1.

2. The process of claim 1 , wherein (HA3−HA1)/HA1≧0.05.

3. The process of claim 1 , wherein at least one of the following conditions is met:
(i) in the treating step (b), the first atmosphere comprises at most 1% by mole of all aromatic compounds; and
(ii) in the treating step (d), the third atmosphere comprises less than 10% by mole of the first aromatic compound.

4. The process of claim 1 , wherein the first atmosphere has an H 2 partial pressure in a range from 100 kPa to 500 kPa.

5. The process of claim 1 , wherein in the treating step (b), the first atmosphere is a flowing stream of gas comprising water at a concentration of less than 100 ppm by mole.

6. The process of claim 1 , wherein in the treating step (d), at least one of the following conditions is met:
(i) the third atmosphere is a flowing stream of gas comprising water at a concentration of less than 100 ppm by mole; and
(ii) the third atmosphere comprises at least 80% by mole of H 2 .

7. The process of claim 1 , wherein the first aromatic compound is benzene.

8. The process of claim 1 , wherein in the treating step (b), the first duration ranges from about 0.5 hour to about 50 hours.

9. The process of claim 8 , wherein in the treating step (b), the first temperature is in a range from about 140° C. to about 360° C.

10. The process of claim 1 , wherein in the treating step (d), at least one of the following conditions is met:
(i) the third duration ranges from about 0.5 hour to about 24 hours; and
(ii) the third temperature is in a range from about 180° C. to about 360° C.

11. The process of claim 1 , wherein the hydrogenating metal component is selected from Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt and mixtures and combinations of at least two thereof.

12. The process of claim 1 , wherein at least one of the following conditions is met:
(i) the hydrogenating metal component comprises palladium; and
(ii) the acid component comprises a MWW zeolite type molecular sieve.

13. A process for producing a cycloalkyl substituted aromatic compound, the process comprising:
(a) providing a hydroalkylation catalyst in a first state comprising an acid component and a hydrogenating metal component;
(b) treating the catalyst in the first state at a first temperature of at least 120° C., in a first atmosphere comprising hydrogen and at most 5% by mole of an aromatic compound for a first duration to produce a catalyst in a second state having a first hydroalkylation activity HA1;
(c) contacting the catalyst in the second state with a first aromatic compound and a second atmosphere comprising hydrogen under a first hydroalkylation condition at a second temperature for a second duration effective to convert at least part of the first aromatic compound into a second aromatic compound comprising an alkyl group, and thereby obtaining a catalyst in a third state having a second hydroalkylation activity HA2, where HA2 is no lower than HA1, the second duration ranges from at least 0.5 hour to about 300 hours, and the second temperature is in a range from 100° C. to about 400° C.;
(d) treating the catalyst in the third state at a third temperature of at least 160° C. in a third atmosphere comprising hydrogen and less than 30% by mole of the first aromatic compound for a third duration to produce a catalyst in a fourth state having a third hydroalkylation activity HA3, where HA3>HA1; and
(e) contacting the catalyst in the fourth state in a hydroalkylation reactor with a third aromatic compound and hydrogen under a second hydroalkylation condition effective to convert at least part of the third aromatic compound to a fourth aromatic compound comprising a cycloalkyl group.

14. The process of claim 13 , wherein (HA3−HA1)/HA1≧0.05.

15. The process of claim 13 , wherein at least one of the following conditions is met:
(i) in the treating step (b), the first atmosphere comprises at most 1% by mole of all aromatic compounds; and
(ii) in the treating step (d), the third atmosphere comprises less than 10% by mole of the first aromatic compound.

16. The process of claim 13 , wherein the first atmosphere has an H 2 partial pressure in a range from 100 kPa to 500 kPa.

17. The process of claim 13 , wherein in the treating step (b), the first atmosphere is a flowing stream of gas comprising water at a concentration of less than 100 ppm by mole.

18. The process of claim 13 , wherein in the treating step (d), at least one of the following conditions is met:
(i) the third atmosphere is a flowing stream of gas comprising water at a concentration of less than 100 ppm by mole; and
(ii) the third atmosphere comprises at least 80% by mole of H 2 .

19. The process of claim 13 , wherein in the treating step (b), at least one of the following conditions is met:
(i) the first duration ranges from about 0.5 hour to about 50 hours; and
(ii) the first temperature is in a range from about 140° C. to about 360° C.

20. The process of claim 13 , wherein in the treating step (d), at least one of the following conditions is met:
(i) the third duration ranges from about 0.5 hour to about 24 hours; and
(ii) the third temperature is in a range from about 180° C. to about 360° C.

21. The process of claim 13 , wherein at least one of the following conditions is met:
(i) the hydrogenating metal component comprises palladium; and
(ii) the acid component comprises a MWW zeolite type molecular sieve.

22. The process of claim 13 , wherein the first aromatic compound and the third aromatic compound are identical, and the second aromatic compound and the fourth aromatic compound are identical.

23. The process of claim 13 , wherein the first aromatic compound and the third aromatic compound are benzene, and the second aromatic compound and the fourth aromatic compound are cyclohexylbenzene.

24. The process of claim 13 , wherein steps (b), (c), (d), and (e) are carried out in a hydroalkylation reactor.

25. The process of claim 13 , wherein at the end of step (e), a catalyst in a fifth state having a

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Kiss Gabor
• Chen Tan-Jen
• Green Thomas E

Classifications

• B01J37/18

  with gases containing free hydrogen · CPC title

• C07C13/28

  Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof · CPC title

• B01J38/10

  using elemental hydrogen · CPC title

• B01J2229/42

  Addition of matrix or binder particles · CPC title

• Y02P20/584

  Recycling of catalysts · CPC title