Mixture containing a monophosphite ligand and the use thereof for catalysis of a hydroformylation reaction

1. A mixture, comprising:

at least one of the two compounds of the structures Ia and Ib:

Ib

wherein

R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group consisting of:

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, halogen, COO—(C 1 -C 12 )-alkyl, CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 ;

X and Y are each independently selected from the group consisting of:

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, —(C 6 -C 2 O-aryl-(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, —(C 1 -C 12 )-alkyl-(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —(C 4 -C 20 )-heteroaryl, —(C 4 -C 20 )-heteroaryl-(C 1 -C 12 )-alkyl, and —(C 5 -C 8 )-cycloalkyl-(C 4 -C 20 )-aryl-CO—(C 6 -C 20 )-aryl,

Z is selected from the group consisting of:

—(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl-, —(C 1 -C 12 )-alkyl-(C 6 -C 2 O-aryl-, —(C 4 -C 20 )-heteroaryl-, —(C 6 -C 20 )-aryl-CO—(C 6 -C 20 )-aryl-, and —(C 6 -C 20 )-aryl-(C 6 -C 20 )-aryl-;

Q is selected from the group consisting of:

—(C 1 -C 18 )-alkyl-, —(C 1 -C 18 )-haloalkyl-, and —NH—(C 1 -C 18 )-alkyl,

wherein the alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl and heteroaryl groups are optionally substituted, and

a compound of the structure IIa:

wherein

R 20 , R 30 , R 40 are each independently selected from the group consisting of:

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, and —(C 3 -C 12 )-cycloalkyl,

two R 20 and R 30 , or R 20 and R 40 , or R 30 and R 40 radicals are optionally bridged to one another, and optionally have a —(C 6 -C 20 )-aryl-(C 6 -C 20 )-aryl unit,

wherein the alkyl, cycloalkyl and aryl groups mentioned are optionally substituted.

2. The mixture according to claim 1 , wherein Q is selected from the group consisting of:

—(C 1 -C 12 )-alkyl-, —(C 1 -C 3 )-alkyl-(C 1 -C 6 )-aryl-, —(C 1 -C 18 )-haloalkyl-, and —NH—(C 1 -C 8 )-alkyl.

3. The mixture according to claim 1 , comprising at least one of the two compounds of one of the structures Ic and Id:

4. The mixture according to claim 1 , wherein X and Y are each independently selected from the group consisting of:

—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-O—(C 1 -C 12 )-alkyl, and —(C 6 -C 20 )-aryl-COO—(C 1 -C 12 )-alkyl.

5. The mixture according to claim 1 , wherein Z is selected from the group consisting of:

—(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-, —(C 6 -C 20 )-aryl-(C 1 -C 12 )-alkyl-, —(C 6 -C 20 )-aryl-CO—(C 6 -C 20 )-aryl-, —(C 1 -C 12 )-alkyl-(C 6 -C 20 )-aryl-, and —(C 6 -C 20 )-aryl-(C 6 -C 20 )-aryl-.

6. The mixture according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 are each independently selected from the group consisting of: —H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

7. The mixture according to claim 1 , wherein X and Y are the same radicals.

8. The mixture according to claim 1 , comprising a compound of the structure Ie:

wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 are each independently selected from the group consisting of:

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, -halogen, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

9. The mixture according to claim 1 , comprising a compound of the structure If:

wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 are each independently selected from the group consisting of:

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, -halogen, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

10. The mixture according to claim 1 , wherein R 20 , R 30 , R 40 each independently selected from the group consisting of:

—(C 1 -C 12 )-alkyl, and —(C 6 -C 20 )-aryl,

wherein the alkyl and aryl groups mentioned are optionally substituted.

11. The mixture according to claim 1 , comprising a compound of the structure IIb:

wherein

R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 35 , R 41 , R 42 , R 43 , R 44 , R 45 are each independently selected from the group consisting of:

—H, —(C 1 -C 12 )-alkyl, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, —(C 6 -C 20 )-aryl, -halogen, —COO—(C 1 -C 12 )-alkyl, —CONH—(C 1 -C 12 )-alkyl, —(C 6 -C 20 )-aryl-CON[(C 1 -C 12 )-alkyl] 2 , —CO—(C 1 -C 12 )-alkyl, —CO—(C 6 -C 20 )-aryl, —COOH, —OH, —SO 3 H, —SO 3 Na, —NO 2 , —CN, —NH 2 , and —N[(C 1 -C 12 )-alkyl] 2 .

12. The mixture according to claim 11 , wherein R 21 , R 22 , R 23 , R 24 , R 25 , R 31 , R 32 , R 33 , R 34 , R 35 , R 41 , R 42 , R 43 , R 44 , R 45 are each independently selected from the group consisting of:

—H, —O—(C 1 -C 12 )-alkyl, —O—(C 6 -C 20 )-aryl, and —(C 6 -C 20 )-aryl.

13. The mixture according to claim 1 , wherein compound Ia is present.

14. The mixture according to claim 1 , wherein compound Ib is present.

15. The mixture according to claim 3 , wherein compound Ic is present.

16. The mixture according to claim 3 , wherein compound Id is present.

17. A complex mixture, comprising:

the mixture according to claim 1 , and

a metal atom selected from the group consisting of Rh, Ru, Co, and Ir.

18. A process of hydroformylating an olefin, comprising:

a) initially charging an olefin;

b) adding

the complex mixture according to claim 17 , or

a mixture according to claim 1 and a compound comprising a metal atom selected from the group consisting of Rh, Ru, Co, and Ir, to obtain a reaction mixture;

c) feeding H 2 and CO into the reaction mixture,

d) heating the reaction mixture, to obtain conversion of the olefin to an aldehyde.

19. The process according to claim 18 , wherein said olefin is a branched, unbranched, terminal or internal olefin.

20. The process according to claim 18 , wherein said aldehyde is a linear aldehyde.