Bisphosphites having 2,4-tert-butylphenyl units and use thereof as ligands in hydroformylation
The invention relates to bisphosphites having 2,4-tert-butylphenyl units and a method for the preparation thereof. Furthermore, the invention relates to the use of the compounds as ligands in a ligand-metal complex. The compound, and also the complex, may be used as a catalytically active composition in hydroformylation reactions.
1. A compound of the formula (I):
where
R 1 , R 3 , R 4 are selected from the group consisting of: —H, —(C 1 -C 12 )-alkyl and —O—(C 1 -C 12 )-alkyl, and
R 2 is —O—(C1-C12)-alkyl,
wherein the alkyl groups mentioned may be substituted as follows:
substituted —(C 1 -C 12 )-alkyl groups and substituted —(C 1 -C 12 )-alkoxy groups, depending on their chain length, may have one or more substituents; the substituents are mutually independently selected from —(C 3 -C 12 )-cycloalkyl, —(C 3 -C 12 )-heterocycloalkyl, —(C 6 -C 20 )-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl;
and at least one of the R 1 , R 3 and R 4 radicals is not —H.
2. The compound according to claim 1 ,
where R 4 is not —H.
3. The compound according to claim 1 ,
where R 4 is —(C 1 -C 12 )-alkyl or —O—(C 1 -C 12 )-alkyl.
4. The compound according to claim 1 ,
where R 4 is —(C 1 -C 12 )-alkyl.
5. The compound according to claim 1 ,
where R 2 is —OMe.
6. The compound according to claim 1 ,
where R 4 is -Me or -tBu.
7. The compound according to claim 1 ,
where R 4 is -tBu.
8. The compound according to claim 1 ,
according to the formula (1):
9. A process comprising the following process steps:
a) initially charging an olefin, forming a reaction mixture,
b) adding a compound according to claim 1 and a substance including a metal selected from: Rh, Ru, Co or Ir,
c) feeding in H 2 and CO,
d) heating the reaction mixture, wherein the olefin is converted to an aldehyde.
10. A complex according to the formula (II):
where
R 1 , R 2 , R 3 and R 4 are —H, —(C 1 -C 12 )-alkyl or —O—(C 1 -C 2 )-alkyl,
wherein the alkyl groups mentioned may be substituted as follows:
substituted —(C 1 -C 12 )-alkyl groups and substituted —(C 1 -C 12 )-alkoxy groups, depending on their chain length, may have one or more substituents; the substituents are mutually independently selected from —(C 3 -C 12 )-cycloalkyl, —(C 3 -C 12 )-heterocycloalkyl, —(C 6 -C 20 )-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl;
and M is Rh, Ru, Co or Ir.
11. The complex according to the formula (III):
where
R 1 , R 2 , R 3 or R 4 are —H, —(C 1 -C 12 )-alkyl or —O—(C 1 -C 12 )-alkyl,
wherein the alkyl groups mentioned may be substituted as follows:
substituted —(C 1 -C 12 )-alkyl groups and substituted —(C 1 -C 12 )-alkoxy groups, depending on their chain length, may have one or more substituents; the substituents are mutually independently selected from —(C 3 -C 12 )-cycloalkyl, —(C 3 -C 12 )-heterocycloalkyl, —(C 6 -C 20 )-aryl, fluorine, chlorine, cyano, formyl, acyl or alkoxycarbonyl;
and M is Rh, Ru, Co or Ir.
12. The complex according to claim 10 ,
where M is Rh.
13. A process comprising the following process steps:
a) initially charging an olefin, forming a reaction mixture,
b) adding a complex according to claim 10 ,
c) feeding in H 2 and CO,
d) heating the reaction mixture, wherein the olefin is converted to an aldehyde.