Isomerization of linear olefins with solid acid catalysts and primary esters

Patent metadata

Field	Value
Publication number	US-12269796-B2
Application number	US-202318501076-A
Country	US
Kind code	B2
Filing date	Nov 3, 2023
Priority date	Aug 24, 2022
Publication date	Apr 8, 2025
Grant date	Apr 8, 2025

Abstract

Isomerized olefin products are produced by contacting an olefin feed containing a C 10 to C 20 normal alpha olefin, a solid acid catalyst, and a C 2 to C 15 primary ester to form the isomerized olefin product. Typical primary esters used in the processes include formates and acetates. Linear olefin compositions are produced that contain at least 80 wt. % C 10 to C 20 linear internal olefins, less than 8 wt. % C 10 to C 20 normal alpha olefins, less than 8 wt. % dimers of C 10 to C 20 olefins, less than 15 wt. % C 10 to C 20 branched olefins, and at least 1 wt. % C 2 to C 15 primary ester and less than 8 wt. % secondary esters.

First claim

I claim:

1. A linear internal olefin composition comprising:
(a) at least 80 wt. % C 10 to C 20 linear internal olefins;
(b) less than or equal to 8 wt. % C 10 to C 20 normal alpha olefin;
(c) less than or equal to 8 wt. % dimers of C 10 to C 20 olefins;
(d) less than or equal to 15 wt. % C 10 to C 20 branched olefins; and
(e) at least 1 wt. % C 2 to C 15 primary ester and less than or equal to 8 wt. % secondary esters.

2. The composition of claim 1 , wherein the composition comprises:
(a) at least 85 wt. % C 10 to C 20 linear internal olefins;
(b) less than or equal to 3 wt. % C 10 to C 20 normal alpha olefin; and
(c) less than or equal to 6 wt. % dimers of C 10 to C 20 olefins.

3. The composition of claim 1 , wherein the composition comprises (e) at least 2 wt. % C 2 to C 15 primary ester and less than or equal to 5 wt. % secondary esters.

4. The composition 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 composition of claim 1 , wherein the normal alpha olefin has a boiling point that is from 75 to 250° C. greater than that of the primary ester.

6. The composition of claim 1 , wherein the primary ester comprises methyl acetate, ethyl acetate, n-propyl acetate, n-butyl acetate, pentyl acetate, isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, decyl acetate, methyl formate, ethyl formate, n-propyl formate, n-butyl formate, pentyl formate, isoamyl formate, hexyl formate, heptyl formate, octyl formate, nonyl formate, decyl formate, or any combination thereof.

7. The composition of claim 1 , wherein the primary ester comprises ethyl acetate.

8. The composition of claim 1 , wherein the linear internal olefins comprise a nearly equilibrium distribution of linear double bond isomers.

9. The composition of claim 1 , wherein the composition comprises (a) from 85 to 97 wt. % C 10 to C 20 linear internal olefins.

10. The composition of claim 1 , wherein the composition comprises (b) from 0.1 to 5 wt. % C 10 to C 20 normal alpha olefin.

11. The composition of claim 1 , wherein the composition comprises (c) from 0.1 to 5 wt. % dimers of C 10 to C 20 olefins.

12. The composition of claim 1 , wherein the composition comprises (d) from 0.5 to 7 wt. % C 10 to C 20 branched olefins.

13. The composition of claim 1 , wherein the composition comprises (e) from 1 to 20 wt. % C 2 to C 15 primary ester and from 0.1 to 5 wt. % secondary esters.

14. A linear internal olefin composition comprising:
(a) from 80 to 97 wt. % C 10 to C 20 linear internal olefins;
(b) from 0.1 to 8 wt. % C 10 to C 20 normal alpha olefin;
(c) from 0.1 to 8 wt. % dimers of C 10 to C 20 olefins;
(d) from 0.1 to 15 wt. % C 10 to C 20 branched olefins; and
(e) from 1 to 15 wt. % C 2 to C 15 primary ester and from 0.1 to 8 wt. % secondary esters.

15. The composition of claim 14 , wherein the normal alpha olefin has a boiling point that is at least 50° C. greater than that of the primary ester.

16. The composition of claim 14 , wherein the normal alpha olefin has a boiling point that is from 75 to 250° C. greater than that of the primary ester.

17. The composition of claim 14 , wherein the primary ester comprises methyl acetate, ethyl acetate, n-propyl acetate, n-butyl acetate, pentyl acetate, isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, decyl acetate, methyl formate, ethyl formate, n-propyl formate, n-butyl formate, pentyl formate, isoamyl formate, hexyl formate, heptyl formate, octyl formate, nonyl formate, decyl formate, or any combination thereof.

18. The composition of claim 14 , wherein the primary ester comprises ethyl acetate.

19. The composition of claim 14 , wherein the linear internal olefins comprise a nearly equilibrium distribution of linear double bond isomers.

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Gee Jeffery C

Classifications

• C07C2531/10

  sulfonated · CPC title

• C07C11/02

  Alkenes · CPC title

• B01J2231/52

  Isomerisation reactions · CPC title

• B01J31/10

  sulfonated · CPC title

• C07C5/2506

  Catalytic processes · CPC title