Catalyst systems that include silyl ether moieties

Patent metadata

Field	Value
Publication number	US-11623901-B1
Application number	US-202217900344-A
Country	US
Kind code	B1
Filing date	Aug 31, 2022
Priority date	Aug 31, 2022
Publication date	Apr 11, 2023
Grant date	Apr 11, 2023

Abstract

Catalyst systems for tetramerizing ethylene to form 1-octene may include a catalyst which may include a chromium compound coordinated with a ligand and a co-catalyst which may include an organoaluminum compound. The ligand may have a chemical structure according to Chemical Structure (I), wherein R 5 , R 6 , and R 7 are each independently chosen from a (C 1 -C 50 ) hydrocarbyl group or a (C 1 -C 50 ) heterohydrocarbyl group, and wherein the (C 1 -C 50 ) hydrocarbyl or (C 1 -C 50 ) heterohydrocarbyl groups of R 5 , R 6 , and R 7 have greater than 10 carbon atoms combined and R A , R B , R C , and R D and R 1 , R 2 , R 3 , and R 4 , are independently chosen from a hydrogen atom or a (C 1 -C 50 ) hydrocarbyl group.

First claim

What is claimed is:

1. A catalyst system for tetramerizing ethylene to form 1-octene, the catalyst system comprising:
a catalyst comprising a chromium compound coordinated with a ligand; and
a co-catalyst comprising an organoaluminum compound,

wherein:
the ligand has the chemical structure:

wherein:
R 5 , R 6 , and R 7 are each independently chosen from a (C 1 -C 50 ) hydrocarbyl group or a (C 1 -C 50 ) heterohydrocarbyl group, and wherein the (C 1 -C 50 ) hydrocarbyl or (C 1 -C 50 ) heterohydrocarbyl groups of R 5 , R 6 , and R 7 have greater than 10 carbon atoms combined; and
R A , R B , R C , and R D and R 1 , R 2 , R 3 , and R 4 , are independently chosen from a hydrogen atom or a (C 1 -C 50 ) hydrocarbyl group.

2. The catalyst system of claim 1 , wherein R 5 , R 6 , and R 7 are each independently an unsubstituted (C 1 -C 50 ) linear or branched alkyl group.

3. The catalyst system of claim 1 , wherein R 5 , R 6 , and R 7 are each independently an unsubstituted (C 4 -C 20 ) linear alkyl group.

4. The catalyst system of claim 1 , wherein one or more of R 5 , R 6 , and R 7 are substituted or unsubstituted aryl groups, and wherein R 5 , R 6 , and R 7 have greater than 15 carbon atoms combined.

5. The catalyst system of claim 1 , wherein one or more of R A , R B , R C , and R D are substituted or unsubstituted aryl moieties.

6. The catalyst system of claim 1 , wherein:
R 1 , R 2 , R 3 , and R 4 are each a hydrogen atom; and
R A , R B , R C , and R D are each a phenyl group.

7. The catalyst system of claim 1 , wherein the chromium compound comprises one or more of an organic chromium salt, an inorganic chromium salt, a chromium coordination complex, and a chromium organometallic complex.

8. The catalyst system of claim 1 , wherein the chromium compound comprises one or more of chromium trichloride tris-tetrahydrofuran complex, chromium dichloride bis-tetrahydrofuran complex, (benzene)tricarbonyl chromium, chromium (III) octanoate, chromium (III) acetylacetonate, chromium hexacarbonyl, chromium (III) 2-ethylhexanoate, and chromium (III) 2,2,6,6-tetramethyl-3,5-heptanedionate.

9. The catalyst system of claim 1 , wherein the catalyst comprises the ligand in an amount such that a molar ratio of the ligand to chromium is from 0.1 to 10.0.

10. The catalyst system of claim 1 , wherein the organoaluminum compound has the structure:

wherein R 8 , R 9 , and R 10 are each selected from the group consisting of a hydrogen atom and an unsubstituted (C 1 -C 20 ) linear or branched alkyl group.

11. The catalyst system of claim 1 , wherein the organoaluminum compound comprises one or more of trimethylaluminium, triethylaluminum, tripropylaluminum, tri-iso-butylaluminum, diisobutylaluminium hydride, trihexylaluminum, tri-n-octylaluminium, methylaluminium dichloride, ethylaluminium dichloride, dimethylaluminium chloride, diethylaluminium chloride, aluminium isopropoxide, ethylaluminiumsesquichloride, methylaluminiumsesquichloride, methylaluminoxane, ethylaluminoxane, and modified methylaluminoxane.

12. The catalyst system of claim 1 , wherein the catalyst system comprises the co-catalyst in an amount such that a molar ratio of the organoaluminum compound to the chromium compound is from 100 to 5000.

13. A method for tetramerizing ethylene to form 1-octene, the method comprising contacting ethylene with the catalyst system of claim 1 to form a product comprising 1-octene.

14. The method of claim 13 , wherein the 1-octene is formed in conditions of:
a reactor pressure from 2 bar to 100 bar; and
a reactor temperature from 30° C. to 180° C.

15. The method of claim 13 , wherein ethylene is contacted with the catalyst system in the presence of a reaction medium, wherein the reaction medium comprises one or more of cyclohexane, methylcyclohexane, decahydronapthalene, chlorobenzene, toluene, xylene, heptane, and isooctane.

Assignees

• Saudi Arabian Oil Co
• Univ King Fahd Pet & Minerals

Inventors

• Jaseer Ea
• Barman Samir
• Villalta Nestor Garcia
• Khawaji Motaz
• Xu Wei
• Almalki Fahad

Classifications

• C07C2531/18

  containing nitrogen, phosphorus, arsenic or antimony · CPC title

• C07C2531/14

  of aluminium or boron · CPC title

• C07C2/34 Primary

  Metal-hydrocarbon complexes · CPC title

• Y02P20/52

  using catalysts, e.g. selective catalysts · CPC title

• B01J31/143

  of aluminium · CPC title