Production of methyl-substituted biphenyl compounds

Patent metadata

Field	Value
Publication number	US-11198660-B2
Application number	US-201716073494-A
Country	US
Kind code	B2
Filing date	Feb 22, 2017
Priority date	Apr 13, 2016
Publication date	Dec 14, 2021
Grant date	Dec 14, 2021

Abstract

In a process for producing a methyl-substituted biphenyl compound, at least one methyl-substituted cyclohexylbenzene compound of the formula:

wherein each of m and n is independently 1, 2, or 3, is contacted with hydrogen in the presence of a hydrogenation catalyst to produce a hydrogenation reaction product comprising at least one methyl-substituted bicyclohexane compound, and the methyl-substituted bicyclohexane compound is then contacted with a dehydrogenation catalyst to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound.

First claim

What is claimed is:

1. A process for producing a methyl-substituted biphenyl compound, the process comprising:
(a) providing a mixture comprising at least one methyl-substituted cyclohexylbenzene compound of the formula (I) below:

wherein step (a) further includes,
(a-1) contacting a feed comprising at least one aromatic hydrocarbon selected from the group consisting of toluene, xylene and mixtures thereof with hydrogen in the presence of a hydroalkylation catalyst under conditions effective to produce a hydroalkylation reaction product comprising methyl-substituted cyclohexylbenzene compounds, (a-2) dehydrogenating at least part of the methyl-substituted cyclohexylbenzene compounds in the hydroalkylation reaction product in the presence of the dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising methyl-substituted biphenyl compounds and unreacted methyl-substituted cyclohexylbenzene compounds, and (a-3) separating at least part of the unreacted methyl-substituted cyclohexylbenzene compounds from the dehydrogenation reaction product to form the mixture;
(b) contacting at least part of the mixture with hydrogen in the presence of a hydrogenation catalyst under conditions effective to produce a hydrogenation reaction product comprising at least one methyl-substituted bicyclohexane compound of the formula (II) below;

wherein each of m and n in formulas (I) and (II) is independently 1, 2, or 3, wherein the hydrogenation reaction product from step (b) comprises less than about 30 wt % of 1, X′- and/or 2-X′-isomers of methyl-substituted bicyclohexane based on the total weight of the isomers of methyl-substituted bicyclohexane, wherein X′ is 2′, 3′, or 4′; and
(c) contacting at least part of the hydrogenation reaction product with a dehydrogenation catalyst under conditions effective to produce a dehydrogenation reaction product comprising at least one methyl-substituted biphenyl compound.

2. The process of claim 1 , wherein each of m and n is, independently, 1 or 2.

3. The process of claim 1 , wherein step (a-2) is carried out in a reaction vessel, and wherein the hydrogenation product of step (b) is recycled to the reaction vessel so that step (c) is carried out in the reaction vessel.

4. The process of claim 1 , wherein the mixture further comprises 2 , X′-isomers of methyl-substituted biphenyl compounds, wherein X′ is 2′, 3′, or 4′.

5. The process of claim 1 , wherein the hydrogenation reaction product from step (b) comprises less than about 20 wt % of 2, X′ isomers of methyl-substituted bicyclohexane based on the total weight of the isomers of methyl-substituted bicyclohexane.

6. The process of claim 1 , wherein the dehydrogenation reaction product from step (c) comprises less than about 20 wt % of 2, X′ isomers based on the total weight of the isomers of the methyl-substituted biphenyl compounds, wherein X′ is 2′, 3′, or 4′.

7. The process of claim 1 , wherein the hydrogenation catalyst comprises at least one member selected from the group consisting of Pd, Pt, Rh, Ru, Os, Ir, Ni, Zn, Sn, Co, combinations thereof, compounds thereof, and mixtures of compounds thereof.

8. The process of claim 7 , wherein the hydrogenation catalyst comprises Pd and/or Pt.

9. The process of claim 1 , wherein the hydrogenation catalyst further comprises a molecular sieve selected from the group consisting of BEA, FAU, MTW, and MWW structure type molecular sieves.

10. The process of claim 9 , wherein the hydrogenation catalyst comprises a molecular sieve of the MCM-22 family.

11. The process of claim 1 , wherein the hydrogenation conditions comprise a temperature of from about 50° C. to about 400° C. and a pressure of from about 100 kPa to about 10,000 kPa.

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

13. The process of claim 12 , wherein the acidic component is selected from the group consisting of BEA, FAU, MTW, and MWW structure type molecular sieves, and the hydrogenation component is selected from the group consisting of Pd, Ru, Ni, Zn, Sn, Co, combinations thereof, compounds thereof, and mixtures of compounds thereof.

14. The process of claim 13 , wherein the molecular sieve is a molecular sieve of the MCM-22 family.

15. The process of claim 1 , wherein the conditions in step (a-1) comprise a temperature of from about 100° C. to about 400° C. and a pressure of from about 100 kPa to about 7,000 kPa.

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

17. The process of claim 1 , wherein the dehydrogenation catalyst comprises an element or compound thereof selected from Group 10 of the Periodic Table of Elements.

18. The process of claim 17 , wherein the dehydrogenation catalyst further comprises tin or a compound thereof.

19. The process of claim 1 , wherein the dehydrogenation conditions in step (c) and/or step (a-2) comprise a temperature of from about 200° C. to about 600° C. and a pressure of from about 100 kPa to about 3550 kPa.

20. A process for producing a biphenyl ester, comprising:
producing at least one methyl-substituted biphenyl compound according to claim 1 ;
contacting the at least one methyl-substituted biphenyl compound with an oxygen source under conditions effective to produce a biphenyl carboxylic acid; and
reacting the biphenyl carboxylic acid with one or more C 4 to C 14 alcohols under conditions effective to produce the biphenyl ester.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Dakka Jihad M
• Decaul Lorenzo C
• Lanci Michael P
• Tang Wei

Classifications

• C07C2523/14

  of germanium, tin or lead · CPC title

• C07C2529/74

  Noble metals · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• B01J29/7057

  Zeolite Beta · CPC title

• C07C2521/08

  Silica · CPC title