IP Library Granted Patent US 11,739,042
Granted Patent B2
US 11,739,042 · App. 18/064,948 · Granted Aug 29, 2023

Process for hydroformylation of olefins using Pt and iodine or bromine

Inventors: Carolin Schneider (Monheim am Rhein, DE); Ralf Jackstell (Rostock, DE); Matthias Beller (Ostseebad Nienhagen, DE); Robert Franke (Marl, DE)
Assignee: EVONIK OPERATIONS GMBH
C07C45/505B01J31/2457B01J37/04B01J2231/321B01J2531/828
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Quick Facts
Patent No.
US 11,739,042
App. No.
18/064,948
Granted
Aug 29, 2023
Kind
B2
Abstract

Process for hydroformylation of olefins using Pt and iodine or bromine.

Claims (39)

1. A process comprising the process steps of:

a) initially charging an olefin;

b) adding a compound of formula (I):

where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are selected from: —H, —(C 1 -C 12 )-alkyl or —(C 6 -C 20 )-aryl, and

R 9 and R 10 are selected from: —(C 1 -C 12 )-alkyl or —(C 6 -C 20 )-aryl,

and, if R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 are —(C 6 -C 20 )-aryl, the aryl ring may have substituents selected from: —(C 1 -C 12 )-alkyl or —O—(C 1 -C 12 )-alkyl;

c) adding a Pt compound capable of forming a complex;

d) adding an iodine compound or bromine compound;

e) feeding in CO and H 2 ;

f) heating the reaction mixture from steps a) to e), to convert the olefin to an aldehyde.

2. The process according to claim 1 ,

where R 2 , R 3 , R 5 , R 6 , R 7 , R 8 are selected from: —(C 1 -C 12 )-alkyl or —(C 6 -C 20 )-aryl.

3. The process according to claim 1 ,

where R 5 , R 6 , R 7 , R 8 are —(C 6 -C 20 )-aryl.

4. The process according to claim 1 ,

where R 2 and R 3 are —(C 1 -C 12 )-alkyl.

5. The process according to claim 1 ,

where R 1 and R 4 are each —H.

6. The process according to claim 1 ,

where R 9 and R 10 are —(C 1 -C 12 )-alkyl.

7. The process according to claim 1 ,

wherein the compound (I) has the structure (1):

8. The process according to claim 1 ,

wherein the Pt compound is selected from: Pt(II)I 2 , Pt(II)Br 2 , Pt(IV)I 4 , Pt(IV)Br 4 , diphenyl(1,5-COD)Pt(II), Pt(II)(acac) 2 , Pt(0)(PPh 3 ) 4 , Pt(0)(DVTS) solution (CAS:68478-92-2), Pt(0)(ethylene)(PPh 3 ) 2 , Pt(II)Br 2 (COD), tris(benzylideneacetone)Pt(0), Pt(II)(OAC) 2 solution, Pt(0)(t-Bu) 2 , Pt(II)(COD)Me 2 , Pt(II)(COD)I 2 , Pt(IV)IMe 3 or Pt(II)(hexafluoroacetylacetonate) 2 .

9. The process according to claim 1 ,

wherein an iodine compound is added in process step d).

10. The process according to claim 9 ,

wherein the iodine compound is added in an amount in the range of 0.1 to 10, measured in equivalents based on Pt.

11. The process according to claim 1 ,

wherein a bromine compound is added in process step d).

12. The process according to claim 11 ,

wherein the bromine compound is added in an amount in the range of 0.1 to 10, measured in equivalents based on Pt.

13. The process according to claim 1 ,

comprising the additional process step e′):

e′) adding a solvent.

14. The process according to claim 1 ,

wherein CO and H 2 is fed in at a pressure in a range from 1 MPa (10 bar) to 6 MPa (60 bar).

15. The process according to claim 1 ,

wherein the reaction mixture is heated to a temperature in the range from 25° C. to 150° C.

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 Jan 25, 2023
From: SCHNEIDER, CAROLIN; JACKSTELL, RALF; BELLER, MATTHIAS; FRANKE, ROBERT
To: EVONIK OPERATIONS GMBH
Reel/Frame 062483/0353 →
Priority Claims (1)
EP 21215374 · Dec 17, 2021 · regional
Continuity (1)
Related Publication 20230192583A1 · Jun 22, 2023
Cited By (1)
US 12,552,822