IP Library Granted Patent US 11,878,294
Granted Patent B2
US 11,878,294 · App. 18/182,063 · Granted Jan 23, 2024

Process for the hydroformylation of olefins using a cobalt precatalyst and a diphosphine ligand

Inventors: Baoxin Zhang (Rostock, DE); Armin Börner (Rostock, DE); Robert Franke (Marl, DE)
Assignee: EVONIK OPERATIONS GMBH
B01J31/24B01J27/12C07C45/28B01J2231/321
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Quick Facts
Patent No.
US 11,878,294
App. No.
18/182,063
Granted
Jan 23, 2024
Kind
B2
Abstract

Process for the hydroformylation of olefins using a cobalt precatalyst and a diphosphine ligand.

Claims (34)

1. A process comprising the process steps of:

a) adding an olefin;

b) adding a cobalt precatalyst;

c) adding a ligand (L) having the structure (I):

where R 1 , R 2 , R 3 and R 4 are selected from:

—H, —(C 1 -C 12 )-alkyl or —(C 6 -C 20 )-aryl;

wherein the ligand is added in a molar ratio to cobalt of L/Co=<0.95/1;

d) supplying of syngas;

e) heating the reaction mixture from a) to d), to convert the olefin into an aldehyde.

2. The process according to claim 1 ,

where R 1 , R 2 , R 3 and R 4 are selected from: —(C 1 -C 12 )-alkyl or —(C 6 -C 20 )-aryl.

3. The process according to claim 1 ,

where R 1 and R 2 are -Ph.

4. The process according to claim 1 ,

where R 1 and R 3 are -Ph.

5. The process according to claim 1 ,

where the ligand has the structure (1):

6. The process according to claim 1 ,

wherein the ligand is added in a molar ratio to cobalt of L/Co=<0.90/1.

7. The process according to claim 1 ,

wherein the ligand is added in a molar ratio to cobalt of L/Co=<0.80/1.

8. The process according to claim 1 ,

wherein the Co precatalyst is initially charged in the form of a solution.

9. The process according to claim 8 ,

wherein the olefin is added to the initially charged Co precatalyst solution.

10. The process according to claim 1 ,

wherein the syngas is supplied in process step d) at a pressure within a range from 1 to 8 MPa (10 to 80 bar).

11. The process according to claim 1 ,

wherein the heating of the reaction mixture in process step e) is to a temperature within a range from 80° C. to 180° C.

12. The process according to claim 1 ,

wherein the cobalt precatalyst is [Co(acac)(C 4 H 8 O 2 ) 4 ] + [BF 4 ] − (V1).

13. The process according to claim 1 ,

wherein the olefin is selected from:

ethene, propene, 1-butene, cis-2-butene, trans-2-butene, mixture of cis- and trans-2-butene, raffinate 1, raffinate 2, isobutene, 1-pentene, 2-pentene, 2-methyl-1-butene, 2-methyl-2-butene, 1-methylcyclohexene, tetramethylethene, 1-octene, 2-octenes, cyclooctene, di-n-butene, diisobutene, undecenes, dodecenes, triisobutene or tri-n-butene.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2024
From: EVONIK OPERATIONS GMBH
To: EVONIK OXENO GMBH & CO. KG
Reel/Frame 066242/0585 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2023
From: ZHANG, BAOXIN; BÖRNER, ARMIN; FRANKE, ROBERT
To: EVONIK OPERATIONS GMBH
Reel/Frame 064056/0877 →
Priority Claims (1)
EP 22163016 · Mar 18, 2022 · regional
Continuity (1)
Related Publication 20230321642A1 · Oct 12, 2023