IP Library Granted Patent US 11,773,042
Granted Patent B2
US 11,773,042 · App. 18/064,946 · Granted Oct 3, 2023

Process for hydroformylation of olefins using Pt and iodine

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 11,773,042
App. No.
18/064,946
Granted
Oct 3, 2023
Kind
B2
Abstract

Process for hydroformylation of olefins using Pt and iodine.

Claims (24)

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, if R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 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;

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 and 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 and 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 —H.

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

7. The process according to claim 1 , wherein the Pt compound is selected from: Pt(II)I 2 , Pt(IV)I 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)(PPh3)2, 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 the Pt compound is selected from: Pt(II)I 2 or Pt(II)(acac) 2 .

9. The process according to claim 1 , wherein the iodine compound is selected from: Pt(II)I 2 or LiI.

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

e′) adding a solvent.

12. The process according to claim 11 , wherein the solvent is selected from: THF, DCM, ACN, heptane, DMF, toluene, texanol, pentane, hexane, octane, isooctane, decane, dodecane, cyclohexane, benzene, xylene, Marlotherm, propylene carbonate, MTBE, diglyme, triglyme, diethyl ether, dioxane, isopropanol, tert-butanol, isononanol, isobutanol, isopentanol or ethyl acetate.

13. 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).

14. The process according to claim 1 , wherein the reaction mixture is heated to a temperature in the range from 25° C. to 150° C.

15. The process according to claim 1 , wherein the olefin is selected from: ethene, propene, 1-butene, cis- and/or trans-2-butene, isobutene, 1,3-butadiene, 1-pentene, cis- and/or trans-2-pentene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, hexene, tetramethylethylene, heptene, 1-octene, 2-octene, di-n -butene or mixtures thereof.

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 24, 2023
From: SCHNEIDER, CAROLIN; JACKSTELL, RALF; BELLER, MATTHIAS; FRANKE, ROBERT
To: EVONIK OPERATIONS GMBH
Reel/Frame 062470/0518 →
Priority Claims (1)
EP 21215350 · Dec 17, 2021 · regional
Continuity (1)
Related Publication 20230192582A1 · Jun 22, 2023