IP Library Granted Patent US 11,866,400
Granted Patent B2
US 11,866,400 · App. 18/064,950 · Granted Jan 9, 2024

Process for hydroformylation of olefins using Pt and DPEphos

Inventors: Carolin Schneider (Monheim am Rhein, DE); Ralf Jackstell (Rostock, DE); Matthias Beller (Ostseebad Nienhagen, DE); Robert Franke (Marl, DE)
Assignee: EVONIK OPERATIONS GMBH
C07C45/505C07C2523/42
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Quick Facts
Patent No.
US 11,866,400
App. No.
18/064,950
Granted
Jan 9, 2024
Kind
B2
Abstract

Process for hydroformylation of olefins using Pt and DPEphos.

Claims (23)

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 at least two of the R 5 , R 6 , R 7 , R 8 radicals are —(C 6 -C 20 )-aryl;

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

d) adding a bromine compound or an iodine 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 5 , R 6 , R 7 and R 8 are —(C 6 -C 20 )-aryl.

3. The process according to claim 1 , where R 5 , R 6 , R 7 and R 8 are -Ph.

4. The process according to claim 1 , where R 1 and R 4 are —H.

5. The process according to claim 1 , where R 2 and R 3 are —H.

6. The process according to claim 1 , wherein the compound of formula (I) has the structure (1):

7. 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 .

8. The process according to claim 1 , wherein a bromine compound which is Pt(II)Br 2 is added in process step d).

9. The process according to claim 8 , wherein the bromine compound is added in an amount in the range of 0.1 to 10, measured in equivalents based on Pt.

10. The process according to claim 1 , wherein in process step d) an iodine compound is added, which is Pt(II)I 2 .

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

12. The process according to claim 1 , comprising the additional process step e′):

e′) adding a solvent.

13. The process according to claim 12 , wherein the solvent is selected from: THF, DCM, ACN, heptane, DMF, toluene, texanol, pentane, hexane, octane, isooctane, decane, dodecane, cyclohexane, benzene, xylene, propylene carbonate, MTBE, diglyme, triglyme, diethyl ether, dioxane, isopropanol, tert-butanol, isononanol, isobutanol, isopentanol, ethyl acetate.

14. The process according to claim 1 , wherein CO and H 2 are 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 Feb 17, 2023
From: SCHNEIDER, CAROLIN; JACKSTELL, RALF; BELLER, MATTHIAS; FRANKE, ROBERT
To: EVONIK OPERATIONS GMBH
Reel/Frame 062734/0362 →