Hydroalkylation catalyst and process for use thereof

Patent metadata

Field	Value
Publication number	US-9725377-B2
Application number	US-201414314557-A
Country	US
Kind code	B2
Filing date	Jun 25, 2014
Priority date	Mar 14, 2013
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

This invention relates to process for producing biphenyl esters, the process comprising:
(a) contacting a feed comprising toluene, xylene or mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less (based upon weight of final catalyst composition), 2) a hydrogenation component present at 0.2 wt % or less (based upon weight of final catalyst composition), and 3) an acidic component comprising a molecular sieve having a twelve membered (or larger) ring pore opening, channel or pocket and a largest pore dimension of 6.0 angstroms or more present at 60 wt % or more, (based upon weight of final catalyst composition); (b) dehydrogenating the hydroalkylation reaction product using a dehydrogenation catalyst to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds; (c) contacting at the dehydrogenation reaction product with an oxidizing gas to convert the methyl-substituted biphenyl compounds to biphenyl carboxylic acids; and (d) reacting the biphenyl carboxylic acids with one or more C 1 to C 14 alcohols to produce biphenyl esters.

First claim

The invention claimed is:

1. A process for producing (methylcyclohexyl)toluene, the process comprising:
(a) contacting a feed comprising toluene with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising (methylcyclohexyl)toluene, wherein the hydroalkylation catalyst comprises: 1) binder present at 40 wt % or less based upon weight of final catalyst composition, 2) a hydrogenation component present at 0.2 wt % or less based upon weight of final catalyst composition, and 3) an acidic component comprising a molecular sieve having a twelve membered or higher ring pore opening, channel or pocket and a largest pore dimension of 6.0 angstroms or more present at 60 wt % or more, based upon weight of final catalyst composition,
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, and wherein the hydroalkylation reaction product comprises at least 60 wt % of the m,3, m,4, p,3 and p,4-isomers of (methylcyclohexyl)toluene based on the total weight of all the (methylcyclohexyl)toluene isomers, and less than 30 wt % of methylcyclohexane.

2. The process of claim 1 , further comprising producing methyl-substituted biphenyl compounds, the process further comprising:
(b) dehydrogenating at least part of the hydroalkylation reaction product in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising a mixture of methyl-substituted biphenyl compounds.

3. The process of claim 2 , further comprising producing biphenyl carboxylic acids, the process further comprising:
(c) contacting at least part of the dehydrogenation reaction product with an oxidizing gas under conditions effective to convert at least part of the methyl-substituted biphenyl compounds to biphenyl carboxylic acids.

4. The process of claim 3 , further comprising producing biphenyl esters, the process further comprising:
(d) reacting the biphenyl carboxylic acids with one or more C 1 to C 3 alcohols under conditions effective to produce biphenyl esters.

5. The process of claim 1 , wherein the molecular sieve is selected from the group consisting of ZSM-12, zeolite Beta, faujasite, mordenite, and mixtures thereof.

6. The process of claim 1 , wherein the molecular sieve is selected from the group consisting of zeolite Y, Ultrastable Y (USY), Dealuminated Y (Deal Y), mordenite and mixtures thereof.

7. The process of claim 1 , wherein the molecular sieve does not comprise a molecular sieve of the MCM-22 family.

8. The process of claim 1 , wherein the binder component of the hydroalkylation catalyst is selected from pseudoboehmite alumina, alumina, silica, titania and mixtures thereof.

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

10. The process of claim 1 , wherein the hydroalkylation reaction product comprises less than 5 wt % of compounds having a methyl group at the 1 position.

11. The process of claim 1 , wherein the feed further comprises benzene and/or at least one alkylbenzene different from toluene.

12. The process of claim 2 , wherein the dehydrogenation catalyst comprises an element or compound thereof selected from Group 10 of the Periodic Table of Elements.

13. The process of claim 2 , wherein the dehydrogenation conditions in (b) include a temperature from about 200° C. to about 600° C. and a pressure from about 100 kPa to about 3550 kPa.

14. The process of claim 1 , wherein the conditions in the contacting (a) include a temperature from about 100° C. to about 400° C. and a pressure from about 100 to about 7,000 kPa.

15. The process of claim 1 , wherein the feed consists essentially of toluene.

16. The process of claim 3 , further comprising producing biphenyl esters, the process further comprising:
(d) reacting the biphenyl carboxylic acids with one or more C 1 to C 14 OXO-alcohols under conditions effective to produce biphenyl esters.

17. The process of claim 16 , where the OXO-alcohol is branched.

18. The process of claim 16 , where the OXO-alcohol has an average branching of from 0.2 to 5.0 branches per molecule.

19. The process of claim 16 , where the OXO-alcohol has 0.35 to 5.0 methyl branches per molecule.

20. The process of claim 1 , wherein the molecular sieve is selected from the group consisting of ZSM-12, zeolite Beta, faujasite, mordenite, zeolite Y, Ultrastable Y (USY), Dealuminated Y (Deal Y), mordenite and mixtures thereof.

21. The process of claim 1 , wherein the hydrogenation component of the hydroalkylation catalyst comprises palladium.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• De Smit Emiel
• Sangar Neeraj
• Salciccioli Michael
• Dakka Jihad M
• Decaul Lorenzo C
• Helton Terry E
• Weigel Scott J

Classifications

• B01J2235/15

  X-ray diffraction · CPC title

• B01J35/50

  characterised by their shape or configuration · CPC title

• B01J35/40

  characterised by dimensions, e.g. grain size (in a colloidal state B01J35/23; crystallite size B01J35/77) · CPC title

• C07C2/74 Primary

  by addition with simultaneous hydrogenation · CPC title

• B01J29/126

  Y-type faujasite · CPC title