Bisphosphites having 2,4-tert-butylphenyl units and use thereof as ligands in hydroformylation

Patent metadata

Field	Value
Publication number	US-10526356-B2
Application number	US-201715805401-A
Country	US
Kind code	B2
Filing date	Nov 7, 2017
Priority date	Nov 8, 2016
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

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.

First claim

The invention claimed is:

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.

Assignees

• Evonik Degussa Gmbh

Inventors

• Dyballa Katrin Marie
• Franke Robert
• Fridag Dirk
• Hess Dieter

Classifications

• C07F15/0073

  Rhodium compounds · CPC title

• C07C45/505

  Asymmetric hydroformylation · CPC title

• C07F9/145 Primary

  with hydroxyaryl compounds · CPC title

• B01J2531/821

  Ruthenium · CPC title

• C07F15/0046

  Ruthenium compounds · CPC title