Biphenyl esters, their production and their use in the manufacture of plasticizers

Patent metadata

Field	Value
Publication number	US-9556103-B2
Application number	US-201514722638-A
Country	US
Kind code	B2
Filing date	May 27, 2015
Priority date	Jun 13, 2014
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

A biphenyl diester useful as a plasticizer having the formula (I):

wherein R 1 is an alkyl group having 5 to 15 carbon atoms and R 2 is a methyl group or a phenyl group.

First claim

What is claimed is:

1. A biphenyl diester having the formula (I):

wherein R 1 is an alkyl group having 5 to 15 carbon atoms and R 2 is a methyl group or a phenyl group.

2. The biphenyl diester of claim 1 , wherein R 1 is an alkyl group having 7 to 14 carbon atoms.

3. The biphenyl diester of claim 1 , wherein R 1 is an alkyl group having 9 to 13 carbon atoms.

4. The biphenyl diester of claim 1 , wherein R 2 is a methyl group.

5. An isomeric mixture of the biphenyl diesters of claim 1 , comprising less than 10 wt % of the 2,X′ isomers, where X′ is 2′, 3′ or 4′.

6. A process for producing the biphenyl diester of claim 1 , the process comprising:
(a) contacting a dimethyl biphenyl compound having the formula (II):

with oxygen in the presence of a solvent comprising acetic acid and/or benzoic acid under conditions effective to oxidize at least part of the dimethyl biphenyl compound to produce an oxidation product comprising a biphenyl monoester having the formula (III):

wherein R 2 is a methyl group or a phenyl group; and
(b) reacting at least part of the biphenyl monoester having the formula (III) with an alcohol having 5 to 15 carbon atoms under conditions effective to produce said biphenyl diester.

7. The process of claim 6 , wherein the solvent comprises acetic acid.

8. The process of claim 6 , wherein the conditions in the contacting (a) include a temperature from 50 to 200° C.

9. The process of claim 6 , wherein the contacting (a) is conducted in the presence of a catalyst comprising cobalt and/or manganese.

10. The process of claim 9 , wherein the contacting (a) is conducted at a molar ratio of dimethyl biphenyl compound to catalyst from 1:0.1 to 1:1.

11. The process of claim 6 , wherein the oxygen concentration in the gas phase during the contacting (a) is less than 5% by volume.

12. The process of claim 6 and further comprising:
(c) separating at least part of the biphenyl monoester having the formula (III) from the oxidation product prior to (b).

13. The process of claim 6 and further comprising:
(1) contacting a feed comprising toluene and hydrogen with a hydroalkylation catalyst under conditions effective to produce a hydroalkylation product comprising (methylcyclohexyl)toluene; and
(2) dehydrogenating at least part of the hydroalkylation product in the presence of a dehydrogenation catalyst under conditions effective to produce a dehydrogenation product comprising the dimethyl biphenyl compound having the formula (II).

14. The process of claim 13 , wherein the hydroalkylation catalyst comprises an acidic component and a hydrogenation component.

15. The process of claim 14 , wherein the acidic component of the hydroalkylation catalyst comprises a molecular sieve.

16. The process of claim 15 , wherein the molecular sieve is selected from the group consisting of BEA, FAU and MTW structure type molecular sieves, molecular sieves of the MCM-22 family and mixtures thereof.

17. The process of claim 15 , wherein the molecular sieve comprises a molecular sieve of the MCM-22 family.

18. The process of claim 14 , wherein the hydrogenation component of the hydroalkylation catalyst selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt and compounds and mixtures thereof.

19. The process of claim 13 , wherein the conditions in (d) include a temperature from about 100° C. to about 400° C. and a pressure from about 100 to about 7,000 kPa.

20. The process of claim 16 , wherein the hydrogenation component of the hydroalkylation catalyst selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt and compounds and mixtures thereof.

21. The process of claim 17 , wherein the hydrogenation component of the hydroalkylation catalyst selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt and compounds and mixtures thereof.

22. The mixture of claim 5 , wherein R 2 is a methyl group and R 1 is an alkyl group having 9 to 13 carbon atoms.

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Dakka Jihad M
• Tang Wei
• Zushma Stephen
• Costello Christine A
• Smirnova Diana
• Vadlamudi Madhavi
• Deflorio Victor

Classifications

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C67/035 Primary

  by reacting carboxylic acids or symmetrical anhydrides with saturated hydrocarbons · CPC title

• C08K5/00

  Use of organic ingredients · CPC title

• C07C69/76

  Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C07C69/78

  Benzoic acid esters · CPC title