IP Library Granted Patent US 10,633,302
Granted Patent B2
US 10,633,302 · App. 16/509,532 · Granted Apr 28, 2020

Process for oligomerization of butene with determination of the proportion of acidic catalysis

Inventors: Fabian Nadolny (Arnsberg, DE); Stephan Peitz (Oer-Erkenschwick, DE); Guido Stochniol (Haltern am See, DE); Robert Franke (Marl, DE); Felix Alscher (Dresden, DE); Cornelia Breitkopf (Dresden, DE); Wladimir Reschetilowski (Radebeul, DE)
Assignee: Evonik Operations GmbH
C07C2/12B01J21/12B01J23/755B01J35/1061B01J37/0201B01J37/08C07C2529/072
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Quick Facts
Patent No.
US 10,633,302
App. No.
16/509,532
Granted
Apr 28, 2020
Kind
B2
Abstract

The invention provides a process for oligomerization of n-butenes using a nickel-containing aluminosilicate catalyst to produce a product mixture whose ratio of 4,4-dimethylhexene to 3,4-dimethylhexene is determined and monitored. The invention further relates to a process for determining the ratio of the amount of the formed 4,4-dimethylhexene or of the formed 3-ethyl-2-methylpentene to the amount of the formed 3,4-dimethylhexene.

Claims (27)

1. A process for oligomerization of n-butenes comprising:

contacting a reactant stream comprising n-butenes with a mesoporous, nickel-containing aluminosilicate catalyst to form a product mixture;

monitoring a ratio of the amount of formed 4,4-dimethylhexene to the amount of formed 3,4-dimethylhexene in the product mixture; and

replacing the catalyst with fresh catalyst when the ratio exceeds a threshold value for the ratio, wherein the threshold value for the ratio is 0.05 or less.

2. The process according to claim 1 , wherein the process for oligomerization is performed at a temperature in the range from 50° C. to 200° C.

3. The process according to claim 1 , wherein the process for oligomerization is performed at a pressure in the range from 10 bar to 70 bar.

4. The process according to claim 1 , wherein the mesoporous nickel-containing aluminosilicate catalyst employed in the process for oligomerization contains nickel, calculated as nickel oxide NiO, in an amount of 0.1% to 51% by weight based on the total composition of the mesoporous nickel-containing aluminosilicate catalyst.

5. The process according to claim 1 , wherein the mesoporous nickel-containing aluminosilicate catalyst employed in the process for oligomerization has an Si/Al ratio of 1 to 100.

6. The process according to claim 1 , wherein the mesoporous nickel-containing aluminosilicate catalyst contains no titanium dioxide and/or no zirconium dioxide.

7. The process according to claim 1 , wherein the process for oligomerization is performed at a temperature in the range from 60° C. to 130° C.

8. The process according to claim 1 , wherein the process for oligomerization is performed at a pressure in the range from 15 bar to 42 bar.

9. The process according to claim 1 , wherein the mesoporous nickel-containing aluminosilicate catalyst employed in the process for oligomerization contains nickel, calculated as nickel oxide NiO, in an amount of 1% to 42% by weight based on the total composition of the mesoporous nickel-containing aluminosilicate catalyst.

10. The process according to claim 1 , wherein the mesoporous nickel-containing aluminosilicate catalyst employed in the process for oligomerization has an Si/Al ratio of 2 to 80.

11. A process for determining a ratio of an amount of formed 4,4-dimethylhexene or of formed 3-ethyl-2-methylpentene to an amount of formed 3,4-dimethylhexene, the process comprising the steps of:

a) oligomerizing a reactant stream comprising n-butenes with a mesoporous nickel-containing aluminosilicate catalyst to form a product stream comprising C8 isomers;

b) quantitative analysis of the product stream obtained from the oligomerization to determine the amounts of the C8 isomers including n-octene, 3-methylheptene, 3,4-dimethylhexene, 4,4-dimethylhexene, 2,3-dimethylhexene and 3-ethyl-2-methylpentene formed during oligomerization;

c) determining the ratio of the amount of the formed 4,4-dimethylhexene or of the formed 3-ethyl-2-methylpentene to the amount of the formed 3,4-dimethylhexene; and

d) replacing the catalyst in step a) with fresh catalyst when the ratio exceeds a threshold value for the ratio, wherein the threshold value for the ratio is 0.05 or less.

12. The process according to claim 11 , wherein the oligomerization in step a) is performed at a temperature in the range from 50° C. to 200° C.

13. The process according to claim 11 , wherein the oligomerization in step a) is performed at a pressure in the range from 10 bar to 70 bar.

14. The process according to claim 11 , wherein the mesoporous nickel-containing aluminosilicate catalyst employed in step a) contains nickel, calculated as nickel oxide NiO, in an amount of 0.1% to 51% by weight based on the total composition of the mesoporous nickel-containing aluminosilicate catalyst.

15. The process according to claim 11 , wherein the mesoporous nickel-containing aluminosilicate catalyst employed in the oligomerization in step a) has an Si/Al ratio of 1 to 100.

16. The process according to claim 11 , wherein the mesoporous nickel-containing aluminosilicate catalyst in step a) contains no titanium dioxide and/or no zirconium dioxide.

17. The process according to claim 11 , wherein the oligomerization is performed at a weight hourly space velocity (WHSV) of between 1 h-1 and 190 h-1.

18. The process according to claim 11 , wherein the quantitative analysis in step b) is performed by gas chromatography.

19. The process according to claim 11 , wherein the oligomerization in step a) is performed at a temperature in the range from 60° C. to 130° C.

20. The process according to claim 11 , wherein the oligomerization in step a) is performed at a pressure in the range from 15 bar to 42 bar.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2023
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 065692/0785 →
CHANGE OF NAME Recorded Dec 27, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051428/0710 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 16, 2019
From: NADOLNY, FABIAN; PEITZ, STEPHAN; STOCHNIOL, GUIDO; FRANKE, ROBERT; ALSCHER, FELIX; BREITKOPF, CORNELIA; RESCHETILOWSKI, WLADIMIR
To: EVONIK DEGUSSA GMBH
Reel/Frame 050729/0812 →
Priority Claims (1)
EP 18185533 · Jul 25, 2018 · regional
Continuity (1)
Related Publication 20200031732A1 · Jan 30, 2020
Cited By (3)
US 12,274,975 US 12,296,301 US 12,485,404