Isomerization of linear olefins with solid acid catalysts and primary esters

1. A process for isomerizing olefins, the process comprising contacting:

(i) an olefin feed comprising a C 10 to C 20 normal alpha olefin;

(ii) a solid acid catalyst resin; and

(iii) a primary ester comprising ethyl acetate;

to form an isomerized olefin reaction product.

2. The process of claim 1 , wherein the olefin feed comprises 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, or any combination thereof.

3. The process of claim 1 , wherein the olefin feed comprises:

at least 85 wt. % C 10 to C 20 normal alpha olefin; and

less than or equal to 10 wt. % branched olefins.

4. The process of claim 1 , wherein the normal alpha olefin has a boiling point that is at least 50° C. greater than that of the primary ester.

5. The process of claim 1 , wherein the solid acid catalyst resin comprises a functionalized styrene-divinylbenzene polymer, a 4-vinylpyridine divinylbenzene polymer, or a tetrafluoroethylene polymer modified with perfluorovinyl ether groups terminated with sulfonate groups, or any combination thereof.

6. The process of claim 1 , wherein the solid acid catalyst resin comprises a sulfonated copolymer of styrene-divinylbenzene.

7. The process of claim 1 , wherein the solid acid catalyst resin contains less than or equal to 1 wt. % of water/moisture.

8. The process of claim 1 , wherein an amount of the primary ester, based on the olefin feed, is from 1 to 25 wt. %.

9. The process of claim 1 , wherein the process is conducted in a stirred tank reactor at a weight ratio of the olefin feed to the solid acid catalyst resin in a range from 1:1 to 100:1.

10. The process of claim 1 , wherein the process is conducted in a fixed bed reactor at an olefin feed WHSV in a range from 0.05 to 5.

11. The process of claim 1 , wherein the isomerized olefin reaction product comprises, based on olefins:

at least 85 wt. % of C 10 to C 20 linear internal olefins;

less than or equal to 3 wt. % of C 10 to C 20 normal alpha olefin; and

less than or equal to 7 wt. % of dimer.

12. The process of claim 1 , wherein the process further comprises a step of removing all or a portion of the primary ester from the isomerized olefin reaction product to form a linear internal olefin product.

13. The process of claim 12 , wherein the removing step comprises flashing, wiped film evaporation, distillation, short path distillation, or any combination thereof.

14. The process of claim 12 , wherein the linear internal olefin product comprises, based on olefins:

at least 80 wt. % of C 10 to C 20 linear internal olefins;

less than or equal to 5 wt. % of C 10 to C 20 normal alpha olefin; and

less than or equal to 10 wt. % of dimer.

15. The process of claim 14 , wherein the linear internal olefin product further comprises:

less than or equal to 8 wt. % of secondary esters; and

less than or equal to 5 wt. % more branched olefins than an amount of branched olefins in the olefin feed.

16. The process of claim 12 , wherein the linear internal olefin product comprises, based on olefins:

at least 85 wt. % of C 10 to C 20 linear internal olefins;

less than or equal to 3 wt. % of C 10 to C 20 normal alpha olefin; and

less than or equal to 5 wt. % of dimer.

17. The process of claim 16 , wherein the linear internal olefin product comprises a nearly equilibrium distribution of linear double bond isomers.

18. The process of claim 1 , wherein:

the olefin feed comprises at least 80 wt. % C 12 to C 20 normal alpha olefin and less than or equal to 12 wt. % branched olefins.

19. The process of claim 18 , wherein the normal alpha olefin has a boiling point that is from 75 to 250° C. greater than that of the primary ester.

20. The process of claim 18 , wherein an amount of the primary ester, based on the olefin feed, is from 2 to 20 wt. %.

21. The process of claim 20 , wherein the solid acid catalyst resin comprises a sulfonated copolymer of styrene-divinylbenzene.