Isomerization of linear olefins with solid acid catalysts and primary esters
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.
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.