IP Library › Granted Patent US 11,186,530
Granted Patent B2
US 11,186,530 · App. 16/850,375 · Granted Nov 30, 2021

Branched C

Inventor: Jeffrey C. Gee (Kingwood, TX)
Assignee: Chevron Phillips Chemical Company, LP
C07C6/04C07C11/02
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Quick Facts
Patent No.
US 11,186,530
App. No.
16/850,375
Granted
Nov 30, 2021
Kind
B2
Abstract

Disclosed herein are compositions containing branched C 18 disubstituted internal olefins and processes for making the compositions by metathesis reaction of a C 10 olefin composition.

Claims (26)

1. A composition comprising branched C 18 disubstituted internal olefins, wherein the branched C 18 disubstituted internal olefins comprise 5,12-dimethyl-8-hexadecene, 5-ethyl-11-methyl-7-pentadecene, 5-n-propyl-10-methyl-6-tetradecene, or any combination thereof.

2. The composition of claim 1 , wherein the branched C 18 disubstituted internal olefins comprise 5,12-dimethyl-8-hexadecene, 5-ethyl-11-methyl-7-pentadecene, and 5-n-propyl-10-methyl-6-tetradecene.

3. The composition of claim 2 , wherein the branched C 18 disubstituted internal olefins further comprise 5,10-diethyl-7-tetradecene, 5-n-propyl-9-ethyl-6-tridecene, and 5,8-di-n-propyl-6-dodecene.

4. The composition of claim 3 , wherein the branched C 18 disubstituted internal olefins further comprise 5-methyl-8-heptadecene, 5-ethyl-7-hexadecene, and 5-n-propyl-6-pentadecene.

5. The composition of claim 2 , wherein the branched C 18 disubstituted internal olefins comprise at least 10 mole % 5,12-dimethyl-8-hexadecene, at least 10 mole % 5-ethyl-11-methyl-7-pentadecene, and at least 10 mole % 5-n-propyl-10-methyl-6-tetradecene.

6. The composition of claim 5 , wherein the branched C 18 disubstituted internal olefins further comprise at least 1 mole % 5,10-diethyl-7-tetradecene, at least 3 mole % 5-n-propyl-9-ethyl-6-tridecene, and at least 3 mole % 5,8-di-n-propyl-6-dodecene.

7. The composition of claim 2 , wherein the branched C 18 disubstituted internal olefins comprises from 18 mole % to 32 mole % 5,12-dimethyl-8-hexadecene, from 17 mole % to 23 mole % 5-ethyl-11-methyl-7-pentadecene, and from 19 mole % to 26 mole % 5-n-propyl-10-methyl-6-tetradecene.

8. The composition of claim 7 , wherein the branched C 18 disubstituted internal olefins further comprise from 2 mole % to 6 mole % 5,10-diethyl-7-tetradecene, from 7 mole % to 13 mole % 5-n-propyl-9-ethyl-6-tridecene, and from 4 mole % to 8 mole % 5,8-di-n-propyl-6-dodecene.

9. The composition of claim 8 , further comprising 9-octadecene.

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, and methyl-1-nonene, and ii) a metathesis catalyst system; and 2) forming a liquid metathesis product comprising branched C 18 disubstituted internal olefins in a reaction zone, where the branched C 18 disubstituted internal olefins comprise 5,12-dimethyl-8-hexadecene, 5-ethyl-11-methyl-7-pentadecene, 5-n-propyl-10-methyl-6-tetradecene, 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 from 20 mole % to 65 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 branched C 18 disubstituted internal olefins comprise 5,12-dimethyl-8-hexadecene, 5-ethyl-11-methyl-7-pentadecene, and 5-n-propyl-10-methyl-6-tetradecene.

14. The process of claim 10 , wherein the branched C 18 disubstituted internal olefins further comprises 5,10-diethyl-7-tetradecene, 5-n-propyl-9-ethyl-6-tridecene, and 5,8-di-n-propyl-6-dodecene.

15. The process of claim 10 , wherein the C 10 olefin composition further comprises 1-decene.

16. The process of claim 15 , wherein the branched C 18 disubstituted internal olefins further comprise 5-methyl-8-heptadecene, 5-ethyl-7-hexadecene, and 5-n-propyl-6-pentadecene.

17. The process of claim 16 , wherein the liquid metathesis product further comprises 9-octadecene.

18. The process of claim 10 , wherein the metathesis catalyst system comprises a metal oxide based metathesis catalyst system, a metal halide based metathesis catalyst system, a metal carbene based metathesis catalyst system, or any combination thereof.

19. The process of claim 18 , wherein the metathesis catalyst system is the metal oxide based metathesis catalyst system, where the metal oxide based metathesis catalyst system comprises cobalt oxide, molybdenum oxide, tungsten oxide, rhenium oxide, or any combination thereof.

20. The process of claim 18 , wherein the metathesis catalyst system is the metal halide based catalyst system where the metal halide based metathesis catalyst system comprises a halide of tungsten, a halide of molybdenum, or any combination thereof.

21. The process of claim 18 , wherein the metathesis catalyst system is the metal carbene based metathesis catalyst system where the metal carbene based metathesis catalyst system comprises tungsten, tantalum, osmium, molybdenum, ruthenium, or any combination thereof.

22. The process of claim 10 , wherein the C 10 olefin composition is a C 10 olefin composition substantially devoid of heteroatomic compounds.

23. The process of claim 22 , further comprising forming the C 10 olefin composition substantially devoid of heteroatomic compounds by removing heteroatomic compounds from the C 10 olefin composition.

24. The process of claim 10 , further comprising:

removing a stream comprising ethylene from the reaction zone; and

recovering the liquid metathesis product from the reaction zone.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2020
From: GEE, JEFFREY C.
To: CHEVRON PHILLIPS CHEMICAL COMPANY LP
Reel/Frame 052422/0203 →
Continuity (1)
Related Publication 20210323896A1 · Oct 21, 2021
Cited By (2)
US 12,540,287 US 12,618,016