PREPARATION OF DIPHENYL COMPOUNDS

• US 20190315665A1
• Filed: 03/27/2019
• Published: 10/17/2019
• Est. Priority Date: 04/12/2018
• Status: Active Grant

• Current Assignee: ExxonMobil Research & Engineering Company (Exxon Mobil Corporation)
• Original Assignee: ExxonMobil Research & Engineering Company (Exxon Mobil Corporation)
• Inventors: Sattler, Aaron, DeFlorio, Victor, Paccagnini, Michele L., Burton, Allen W.
• Granted Patent: US 10,858,298 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 1/24 by elimination of water
• CPC Class Codes: C07C 1/247 by splitting of cyclic ethers
• CPC Class Codes: C07C 15/14 all phenyl groups being directly linked
• CPC Class Codes: C07C 5/367 Formation of an aromatic six-membered ring from an existing six-membered ring, e.g. dehydrogenation of ethylcyclohexane to ethylbenzene
• CPC Class Codes: C07C 6/04 at a carbon-to-carbon double bond
• CPC Class Codes: C07D 493/08 Bridged systems

Abstract

This disclosure relates to the preparation of diphenyl compounds, especially dimethylbiphenyl compounds, in which there is one methyl group on each ring, and their oxidized analogues. These compounds, and particularly alkylated biphenyl compounds and biphenylcarboxylic acids, alcohols and esters, are useful intermediates in the production of a variety of commercially valuable products, including polyesters and plasticizers for PVC and other polymer compositions.

Claims

1. A process for producing a biphenyl compound, the process comprising:

(a1) reacting furan or a substituted furan compound having the formula (I);

2. The process of claim 1, wherein the reacting step (a1) is conducted in the presence of a catalyst.

3. The process of claim 2, wherein the catalyst comprises an acidic molecular sieve or a Lewis acid.

4. The process of claim 1, wherein the conditions in (a1) include a temperature from about 100°

C. to about 400°

C.

5. The process of claim 1, wherein the conditions in (a1) include a pressure in excess of 540 kPa-a.

6. The process of claim 1, wherein the reacting (a1) and dehydrating (b1) are conducted in the same reaction zone.

7. The process of claim 1, wherein the compound having the formula (I) comprises furan substituted at the 2- or 3-position.

8. The process of claim 1, wherein where R¹ is —

CH₃ or —

CHO.

9. The process of claim 1, wherein the compound having the formula (II) comprises styrene or a substituted styrene and the compound of formula (IV) is a biphenyl compound.

10. The process of claim 1, wherein the compound having the formula (II) comprises para-methylstyrene.

11. The process of claim 1, wherein the compound having the formula (II) comprises vinylcyclohexane, vinylcyclohexene or a substituted analogue thereof.

12. The process of claim 11 and further comprising:

(c1) dehydrogenating the compound of formula (IV) to produce a biphenyl compound.

14. The process of claim 1, wherein the reacting step (a2) is conducted in the presence of a catalyst.

15. The process of claim 14, wherein the catalyst comprises an acidic molecular sieve or a Lewis acid.

13. A process for producing a biphenyl compound, the process comprising:

(a2) reacting furan or a substituted furan compound having the formula (I);

16. The process of claim 13, wherein the conditions in (a2) include a temperature from about 100°

C. to about 400°

C.

17. The process of claim 13, wherein the conditions in (a2) include a pressure of 270 to 540 kPa-a.

18. The process of claim 13, wherein the compound having the formula (I) comprises furan substituted at the 2- or 3-position.

19. The process of claim 13, wherein where R¹ is —

CH₃ or —

CHO.

20. The process of claim 13, wherein the compound having the formula (II) comprises styrene or a substituted styrene and the compound of formula (VII) is a biphenyl compound.

21. The process of claim 13, wherein the compound having the formula (II) comprises para-methylstyrene.

22. The process of claim 13, wherein the compound having the formula (II) comprises vinylcyclohexane, vinylcyclohexene or a substituted analogue thereof.

23. The process of claim 13 and further comprising:

(d2) dehydrogenating the compound of formula (VII) to produce a diphenyl compound.

24. A product composition comprising a mixture of the compound of formula (IV) and the compound of formula (I) and/or the compound of formula (II).

25. A product composition comprising a mixture of the compound of formula (VII) and one or more of the compounds of formula (I), formula (II) and formula (V).