Heavy oligomer compositions of a selective 1-hexene and 1-octene catalyst

Patent metadata

Field	Value
Publication number	US-12017971-B2
Application number	US-202318340961-A
Country	US
Kind code	B2
Filing date	Jun 26, 2023
Priority date	Sep 7, 2021
Publication date	Jun 25, 2024
Grant date	Jun 25, 2024

Abstract

A C10 hydrocarbon composition of greater than 55 wt. % C10 mono-olefins contains 1-decene, 2-butyl-1-hexene, 3-propyl-1-heptene, 4-ethyl-1-octene, 4-penten-1-yl-cyclopentane, and 5-methyl-1-nonene. A C12 hydrocarbon composition of greater than 60 wt. % C12 mono-olefins contains 1-dodecene, 6-hepten-1-yl-cyclopentane, heptylcyclopentane and n-dodecane. A C14 hydrocarbon composition of greater than 60 wt. % C14 mono-olefins contains 1-tetradecene, 8-nonen-1-yl-cyclopentane, n-tetradecane, and nonylcyclopentane.

First claim

What is claimed is:

1. A composition comprising at least 55 wt. % C 10 mono-olefins, the C 10 mono-olefins comprising:
i) from 12 to 42 wt. % 1-decene;
ii) at least 0.5 wt. % 2-butyl-1-hexene;
iii) at least 1 wt. % 3-propyl-1-heptene;
iv) from 0.5 to 12 wt. % wt. % 4-ethyl-1-octene;
v) at least 4 wt. % 4-penten-1-yl-cyclopentane; and
vi) from 2 to 40 wt. % 5-methyl-1-nonene.

2. The composition of claim 1 , wherein the C 10 mono-olefins comprise from 20 to 30 wt. % 1-decene.

3. The composition of claim 1 , wherein the C 10 mono-olefins comprise from 1 to 5 wt. % 4-ethyl-1-octene.

4. The composition of claim 1 , wherein the C 10 mono-olefins comprise a weight ratio of 4-penten-1-yl-cyclopentane to 1-decene from 0.2:1 to 1.2:1.

5. The composition of claim 1 , wherein the composition comprises:
from 65 to 85 wt. % C 10 mono-olefins; and
further comprises from 5 to 13 wt. % pentylcyclopentane.

6. The composition of claim 5 , wherein the Cm mono-olefins comprise:
from 2 to 6 wt. % 2-butyl-1-hexene;
from 5 to 22 wt. % 3-propyl-1-heptene;
from 10 to 25 wt. % 4-penten-1-yl-cyclopentane; and
from 10 to 28 wt. % 5-methyl-1-nonene.

7. A composition comprising at least 60 wt. % C 12 mono-olefins, the C 12 mono-olefins comprising:
i) from 9 to 35 wt. % 1-dodecene; and
ii) at least 0.5 wt. % 6-hepten-1-yl-cyclopentane;
wherein the composition further comprises heptylcyclopentane and n-dodecane at a weight ratio of heptylcyclopentane to n-dodecane from 0:3:1 to 8:1.

8. The composition of claim 7 , wherein the C 12 mono-olefins comprise:
from 12 to 29 wt. % 1-dodecene; and
from 3 to 20 wt. % 6-hepten-1-yl-cyclopentane.

9. The composition of claim 7 , wherein:
the C 12 mono-olefins further comprise from 35 to 85 wt. % non-cyclic branched C 12 mono-olefins; and
the non-cyclic branched C 12 mono-olefins comprise 5-methyl-1-undecene, 7-methyl-1-undecene, 4-ethyl-1-decene, 6-ethyl-1-decene, 3-propyl-1-nonene, 5-propyl-1-nonene, 2-butyl-1-octene, 3-butyl-1-octene, 4-butyl-1-octene, or any combination thereof.

10. The composition of claim 7 , wherein:
the composition comprises from 70 to 98 wt. % C 12 mono-olefins; and
the weight ratio of heptylcyclopentane to n-dodecane is from 0.8:1 to 4:1.

11. The composition of claim 10 , wherein the C 12 mono-olefins comprise a weight ratio of 1-dodecene to 6-hepten-1-yl-cyclopentane from 1.5:1 to 4:1.

12. A composition comprising at least 60 wt. % C 14 mono-olefins, the C 14 mono-olefins comprising:
i) from 14 to 45 wt. % 1-tetradecene; and
ii) from 0.75 to 28 wt. % 8-nonen-1-yl-cyclopentane;
wherein the composition further comprises a total of from 4 to 28 wt. % of n-tetradecane and nonylcyclopentane.

13. The composition of claim 12 , wherein the composition comprises a total of from 6 to 20 wt. % n-tetradecane and nonylcyclopentane.

14. The composition of claim 12 , wherein the C 14 mono-olefins comprise:
from 18 to 36 wt. % 1-tetradecene; and
from 5 to 15 wt. % 8-nonen-1-yl-cyclopentane.

15. The composition of claim 12 , wherein:
the C 14 mono-olefins further comprise from 36 to 78 wt. % non-cyclic branched C 14 mono-olefins; and
the non-cyclic branched C 14 mono-olefins comprise 7-methyl-1-tridecene, 6-ethyl-1-dodecene, 5-propyl-1-undecene, 4-butyl-1-decene, 3-pentyl-1-nonene, or any combination thereof.

16. The composition of claim 12 , wherein:
the composition comprises from 75 to 98 wt. % C 14 mono-olefins; and
a weight ratio of 1-tetradecene to 8-nonen-1-yl-cyclopentane is from 1.5:1 to 9:1.

17. A composition comprising:
(a) a C 10 composition comprising at least 55 wt. % C 10 mono-olefins, the C 10 mono-olefins comprising:
i) from 12 to 42 wt. % 1-decene;
ii) at least 0.5 wt. % 2-butyl-1-hexene;
iii) at least 1 wt. % 3-propyl-1-heptene;
iv) from 0.5 to 12 wt. % wt. % 4-ethyl-1-octene;
v) at least 4 wt. % 4-penten-1-yl-cyclopentane; and
vi) from 2 to 40 wt. % 5-methyl-1-nonene;

(b) a C 12 composition comprising at least 60 wt. % C 12 mono-olefins, the C 12 mono-olefins comprising:
i) from 9 to 35 wt. % 1-dodecene; and
ii) at least 0.5 wt. % 6-hepten-1-yl-cyclopentane;
wherein the composition further comprises heptylcyclopentane and n-dodecane at a weight ratio of heptylcyclopentane to n-dodecane from 0:3:1 to 8:1; and

(c) a C 14 composition comprising at least 60 wt. % C 14 mono-olefins, the C 14 mono-olefins comprising:
i) from 14 to 45 wt. % 1-tetradecene; and
ii) from 0.75 to 28 wt. % 8-nonen-1-yl-cyclopentane;
wherein the composition further comprises a total of from 4 to 28 wt. % of n-tetradecane and nonylcyclopentane.

18. The composition of claim 17 , wherein the composition comprises:
from 25 to 47 wt. % of the C 10 composition;
from 30 to 55 wt. % of the C 12 composition; and
from 12 to 35 wt. % of the C 14 composition.

19. The composition of claim 18 , wherein the composition comprises from 75 to 95 wt. % of C 10-14 mono-olefins.

20. The composition of claim 17 , further comprising C 16 -18 hydrocarbons.

21. The composition of claim 20 , wherein:
the composition comprises from 70 to 98 wt. % of C 10-18 mono-olefins; and
the composition comprises:
from 15 to 40 wt. % of the C 10 composition;
from 19 to 40 wt. % of the C 12 composition;
from 7 to 25 wt. % of the C 14 composition; and
from 18 to 40 wt. % of C 16-18 hydrocarbons.

22. The composition of claim 21 , wherein the composition comprises from 80 to 95 wt. % of C 10-18 mono-olefins.

Assignees

• Chevron Phillips Chemical Co Lp

Inventors

• Sydora Orson L

Classifications

• C10G2400/22

  Higher olefins · CPC title

• C07C11/107

  with six carbon atoms · CPC title

• C07C13/10

  with a cyclopentane ring · CPC title

• C07C9/15

  Straight-chain hydrocarbons · CPC title

• C07C13/11

  substituted by unsaturated hydrocarbon groups · CPC title