IP Library › Granted Patent US 11,174,205
Granted Patent B2
US 11,174,205 · App. 16/850,407 · Granted Nov 16, 2021

C

Inventor: Jeffrey C. Gee (Kingwood, TX)
Assignee: Chevron Phillips Chemical Company, LP
C07C2/24B01J31/143B01J31/38C07C7/04C07C11/02C07C2531/14C07C2531/38
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Quick Facts
Patent No.
US 11,174,205
App. No.
16/850,407
Granted
Nov 16, 2021
Kind
B2
Abstract

Disclosed herein are compositions containing branched C 20 2-substituted alpha olefins and processes for making the compositions by dimerization reaction of a C 10 olefin composition.

Claims (22)

1. A composition comprising at least 50 mole % C 20 2-substituted alpha olefins, wherein the C 20 2-substituted alpha olefins comprise 2-(3-methylheptyl)-7-methyl-1-undecene, 2-(4-octyl)-7-methyl-1-undecene, 2-(3-methylheptyl)-5-propyl-1-nonene, 2-(2-ethylhexyl)-7-methyl-1-undecene, 2-(3-methylheptyl)-6-ethyl-1-decene, or any combination thereof.

2. The composition of claim 1 , wherein the C 20 2-substituted alpha olefins comprise 2-(3-methylheptyl)-7-methyl-1-undecene, 2-(4-octyl)-7-methyl-1-undecene, 2-(3-methylheptyl)-5-propyl-1-nonene, 2-(2-ethylhexyl)-7-methyl-1-undecene, and 2-(3-methylheptyl)-6-ethyl-1-decene.

3. The composition of claim 2 , wherein the C 20 2-substituted alpha olefins comprise at least 10 mole % 2-(3-methylheptyl)-7-methyl-1-undecene, at least 5 mole % 2-(4-octyl)-7-methyl-1-undecene, at least 5 mole % 2-(3-methylheptyl)-5-propyl-1-nonene, at least 5 mole % 2-(2-ethylhexyl)-7-methyl-1-undecene, and at least 5 mole % 2-(3-methylheptyl)-6-ethyl-1-decene.

4. The composition of claim 2 , wherein the C 20 2-substituted alpha olefins comprise from 20 mole % to 30 mole % 2-(3-methylheptyl)-7-methyl-1-undecene, from 7 mole % to 15 mole % 2-(4-octyl)-7-methyl-1-undecene, from 7 mole % to 15 mole % 2-(3-methylheptyl)-5-propyl-1-nonene, from 7 mole % to 15 mole % 2-(2-ethylhexyl)-7-methyl-1-undecene, and from 7 mole % to 15 mole % 2-(3-methylheptyl)-6-ethyl-1-decene.

5. The composition of claim 2 , wherein the C 20 2-substituted alpha olefins further comprise 2-(4-octyl)-5-propyl-1-nonene, 2-(4-octyl)-6-ethyl-1-decene, 2-(2-ethylhexyl)-5-propyl-1-nonene, and 2-(2-ethylhexyl)-6-ethyl-1-decene.

6. The composition of claim 5 , wherein the C 20 2-substituted alpha olefins comprise at least 3 mole % 2-(4-octyl)-5-propyl-1-nonene, at least 3 mole % 2-(4-octyl)-6-ethyl-1-decene, at least 3 mole % 2-(2-ethylhexyl)-5-propyl-1-nonene, and at least 2.5 mole % 2-(2-ethylhexyl)-6-ethyl-1-decene.

7. The composition of claim 6 , wherein the C 20 2-substituted alpha olefins comprise from 3 mole % to 9 mole % 2-(4-octyl)-5-propyl-1-nonene, from 3 mole % to 9 mole % 2-(4-octyl)-6-ethyl-1-decene, from 3 mole % to 9 mole % 2-(2-ethylhexyl)-5-propyl-1-nonene, and from 2.5 mole % to 8 mole % 2-(2-ethylhexyl)-6-ethyl-1-decene.

8. The composition of claim 5 , wherein the C 20 2-substituted alpha olefins further comprise 2-(3-methylheptyl)-1-dodecene, 2-octyl-7-methyl-1-undecene, 2-(4-octyl)-1-dodecene, 2-(3-propylheptyl)-1-decene, 2-(2-ethylhexyl)-1-dodecene, 2-octyl-6-ethyl-1-decene, and 2-octyl-1-dodecene.

9. The composition of claim 8 , wherein the C 20 2-substituted alpha olefins comprise at least 2 mole % of the 2-(3-methylheptyl)-1-dodecene, at least 2 mole % of the 2-octyl-7-methyl-1-undecene, at least 0.5 mole % of the 2-(4-octyl)-1-dodecene, at least 0.5 mole % of the 2-(3-propylheptyl)-1-decene, at least 0.5 mole % of the 2-(2-ethylhexyl)-1-dodecene, at least 0.5 mole % of the 2-octyl-6-ethyl-1-decene, and at least 0.1 mole % of the 2-octyl-1-dodecene.

10. A process comprising: 1) contacting i) a C 10 olefin composition comprising branched C 10 olefins, the branched C 10 olefins comprising 3-propyl-1-heptene, 4-ethyl-1-octene, 5-methyl-1-nonene or any combination thereof, and ii) a dimerization catalyst or dimerization catalyst system; 2) forming a reaction product comprising at least 50 mole % C 20 2-substituted alpha olefins; and 3) isolating a composition comprising at least 50 mole % C 20 2-substituted alpha olefins, wherein the C 20 2-substituted alpha olefins comprise 2-(3-methylheptyl)-7-methyl-1-undecene, 2-(4-octyl)-7-methyl-1-undecene, 2-(3-methylheptyl)-5-propyl-1-nonene, 2-(2-ethylhexyl)-7-methyl-1-undecene, 2-(3-methylheptyl)-6-ethyl-1-decene, or any combination thereof.

11. The process of claim 10 , wherein the branched C 10 olefins comprise at least 8 mole % 3-propyl-1-heptene, at least 6 mole % 4-ethyl-1-octene, and at least 20 mole % 5-methyl-1-nonene.

12. The process of claim 10 , wherein the branched C 10 olefins comprise from 8 mole % to 35 mole % 3-propyl-1-heptene, from 6 mole % to 30 mole % 4-ethyl-1-octene, and from 20 mole % to 65 mole % 5-methyl-1-nonene.

13. The process of claim 10 , wherein the dimerization catalyst or dimerization catalyst system comprises i) an alkylaluminum compound, ii) a zirconium compound, or iii) a metallocene compound.

14. The process of claim 13 , wherein the dimerization catalyst is the alkylaluminum compound and the alkylaluminum compound consists essentially of a trialkylaluminum compound.

15. The process of claim 13 , wherein the dimerization catalyst system is the zirconium compound and an aluminoxane, wherein the zirconium compound comprises zirconium dichloride.

16. The process of claim 13 , wherein the dimerization catalyst system is the metallocene compound and (a) an aluminoxane or (b) a non-coordinating anion and an alkylaluminum compound.

17. The process of claim 10 , wherein the C 20 2-substituted alpha olefins comprise 2-(3-methylheptyl)-7-methyl-1-undecene, 2-(4-octyl)-7-methyl-1-undecene, 2-(3-methylheptyl)-5-propyl-1-nonene, 2-(2-ethylhexyl)-7-methyl-1-undecene, and 2-(3-methylheptyl)-6-ethyl-1-decene.

18. The process of claim 17 , wherein the C 20 2-substituted alpha olefins further comprise 2-(4-octyl)-5-propyl-1-nonene, 2-(4-octyl)-6-ethyl-1-decene, 2-(2-ethylhexyl)-5-propyl-1-nonene, and the 2-(2-ethylhexyl)-6-ethyl-1-decene.

19. The process of claim 18 , wherein the C 20 2-substituted alpha olefins further comprise 2-(3-methylheptyl)-1-dodecene, 2-octyl-7-methyl-1-undecene, 2-(4-octyl)-1-dodecene, the 2-(3-propylheptyl)-1-decene, 2-(2-ethylhexyl)-1-dodecene, 2-octyl-6-ethyl-1-decene, and 2-octyl-1-dodecene.

20. The process of claim 10 , where the C 10 olefin composition is substantially devoid of heteroatomic compounds.

21. The process of claim 20 , further comprising forming the C 10 olefin composition substantially devoid of heteroatomic compounds by removing a heteroatomic compound from the C 10 olefin composition.

22. The process of claim 10 , wherein isolating the composition comprising at least 50 mole % C 20 2-substituted alpha olefins comprises distilling the dimerization product.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2020
From: GEE, JEFFREY C.
To: CHEVRON PHILLIPS CHEMICAL COMPANY LP
Reel/Frame 052422/0219 →
Continuity (1)
Related Publication 20210323892A1 · Oct 21, 2021
Cited By (2)
US 12,540,287 US 12,618,016