Preparation and use of phenylstyrene

Patent metadata

Field	Value
Publication number	US-10787399-B2
Application number	US-201615946077-A
Country	US
Kind code	B2
Filing date	Oct 14, 2016
Priority date	Nov 20, 2015
Publication date	Sep 29, 2020
Grant date	Sep 29, 2020

Abstract

A process for producing phenylstyrene comprises contacting benzene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation product comprising cyclohexylbenzene. At least part of the cyclohexylbenzene is then contacted with ethylbenzene in the presence of a transalkylation catalyst under conditions effective to produce a transalkylation product comprising cyclohexylethylbenzene and/or with ethylene in the presence of an alkylation catalyst under conditions effective to produce an alkylation product comprising cyclohexylethylbenzene. At least part of the cyclohexylethylbenzene is then contacted with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation product comprising phenylstyrene.

First claim

What is claimed is:

1. A process for producing phenylstyrene, the process comprising:
(a1) contacting benzene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation product comprising cyclohexylbenzene;
(b1) converting at least part of the cyclohexylbenzene from (a1) to cyclohexylethylbenzene by contacting the cyclohexylbenzene with ethylbenzene in the presence of a transalkylation catalyst under conditions effective to produce a transalkylation product comprising cyclohexylethylbenzene; and/or contacting the cyclohexylbenzene with ethylene in the presence of an alkylation catalyst under conditions effective to produce an alkylation product comprising cyclohexylethylbenzene; and
(c1) contacting at least part of the cyclohexylethylbenzene from (b1) with at least one dehydrogenation catalyst under conditions effective to produce a dehydrogenation product comprising phenylstyrene.

2. The process of claim 1 , wherein the contacting (a1) is conducted under conditions including a temperature from about 100° C. to about 400° C. and a pressure from about 100 to about 7,000 kPa.

3. The process of claim 1 , wherein the hydroalkylation catalyst comprises an acidic component and a hydrogenation component.

4. The process of claim 3 , wherein the acidic component of the hydroalkylation catalyst comprises a molecular sieve.

5. The process of claim 4 , wherein the molecular sieve comprises a molecular sieve of the MCM-22 family.

6. The process of claim 3 , wherein the hydrogenation component of the hydroalkylation catalyst is selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt, and compounds and mixtures thereof.

7. The process of claim 1 , wherein a molar ratio of hydrogen to benzene supplied to the contacting (a1) is from about 0.15:1 to about 15:1.

8. The process of claim 1 , wherein the converting (b1) comprises contacting the cyclohexylbenzene with ethylbenzene in the presence of a transalkylation catalyst under conditions including a temperature from about 100° C. to about 400° C. and a pressure from about 100 to about 10,000 kPa-absolute.

9. The process of claim 8 , wherein the transalkylation catalyst comprises a molecular sieve.

10. The process of claim 8 , wherein the transalkylation catalyst comprises a molecular sieve selected from the group consisting of BEA, FAU, MOR, MFI, MWW framework molecular sieves and mixtures thereof.

11. The process of claim 1 , wherein the converting (b1) comprises contacting the cyclohexylbenzene with ethylene in the presence of an alkylation catalyst under conditions including a temperature from about 100° C. to about 500° C. and a pressure from about 100 to about 10,000 kPa-absolute.

12. The process of claim 11 , wherein the alkylation catalyst comprises a molecular sieve.

13. The process of claim 1 , wherein the contacting (c1) to convert the cyclohexylethylbenzene to phenylstyrene is conducted in a single step.

14. The process of claim 13 , wherein the contacting (c1) is conducted in the presence of a dehydrogenation catalyst comprising a metal or oxide form of Fe, K, Cr, Mo, Ce, Zn, Bi, Ca, Co, Cu, Li, Mg, V, W, Zr, Ti, Mn, B, Al, Si, Pt, Pd, Ni, Ru, Re, Sn, Na, or any combination thereof.

15. The process of claim 13 , wherein the contacting (c1) is conducted in the presence of a hydrogen or steam co-feed.

16. The process of claim 1 , wherein the contacting (c1) to convert the cyclohexylethylbenzene to phenylstyrene comprises:
(i) contacting at least part of the cyclohexylethylbenzene from (b1) with a first dehydrogenation catalyst to produce a first dehydrogenation product comprising ethylbiphenyl; and
(ii) contacting at least part of the ethylbiphenyl from (i) with a second dehydrogenation catalyst to produce a second dehydrogenation product comprising phenylstyrene.

17. The process of claim 16 , wherein the first dehydrogenation catalyst comprises an element or compound thereof from Group 10 of the Periodic Table of the Elements and an element or compound thereof from Group 14 of the Periodic Table.

18. The process of claim 16 , wherein the first dehydrogenation catalyst comprises silica.

19. The process of claim 17 , wherein the second dehydrogenation catalyst comprises an oxide or metal form of Fe, K, Cr, Mo, Ce, Zn, Bi, Ca, Co, Cu, Li, Mg, V, W, Zr, Ti, Mn, B, Al, Si, Pt, Pd, Ni, Ru, Re, Sn, Na, or any combination thereof.

20. The process of claim 1 , and further comprising:
(d) separating at least part of the transalkylation product into a first fraction having an increased concentration of at least one isomer of cyclohexylethylbenzene as compared with the transalkylation product and a second fraction having a decreased concentration of at least one isomer of cyclohexylethylbenzene as compared with the transalkylation product;
(e) supplying at least part of the first fraction to the contacting (c1); and
(d) recycling the second fraction to the contacting (b1).

21. The process of claim 20 , wherein the at least one isomer of cyclohexylethylbenzene comprises 1-cyclohexyl-4-ethylbenzene.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Salciccioli Michael
• Galuska Alan A
• Ghose Ranjita
• Levin Doron
• Zhao Mosha H

Classifications

• C07C2523/36

  Rhenium · CPC title

• C07C2523/40

  of the platinum group metals · CPC title

• C07C2523/10

  of rare earths · CPC title

• C07C2523/44

  Palladium · CPC title

• C07C2523/42

  Platinum · CPC title