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

Abstract

The invention relates to bisphosphites having 2,4-dimethylphenyl 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 . Compound of the formula (I): 
       
         
           
           
               
               
           
         
         where 
         R 2 , R 3 , R 4  are selected from: —H, —(C 1 -C 12 )-alkyl, —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. 
       
     
     
         2 . Compound according to  claim 1 ,
 where R 2  is selected from: -Me, -tBu, —OMe.   
     
     
         3 . Compound according to  claim 1 ,
 where R 2  is —OMe.   
     
     
         4 . Compound according to  claim 1 ,
 where R 4  is selected from: -Me, -tBu, —OMe.   
     
     
         5 . Compound according to  claim 1 ,
 where R 4  is -tBu.   
     
     
         6 . Compound according to  claim 1 ,
 according to the formula (1):   
       
         
           
           
               
               
           
         
       
     
     
         7 . Complex according to the formula (II): 
       
         
           
           
               
               
           
         
         where 
         R 2 , R 3 , R 4  are selected from: —H, —(C 1 -C 12 )-alkyl, —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 selected from: Rh, Ru, Co, Ir. 
       
     
     
         8 . Complex according to the formula (III): 
       
         
           
           
               
               
           
         
         where 
         R 2 , R 3 , R 4  are selected from: —H, —(C 1 -C 12 )-alkyl, —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 selected from: Rh, Ru, Co, Ir. 
       
     
     
         9 . Complex according to  claim 7 ,
 where M=Rh.   
     
     
         10 . Use of a compound according to  claim 1 ,
 in a ligand-metal complex for catalysis of a hydroformylation reaction.   
     
     
         11 . Process comprising the following process steps:
 a) initially charging an olefin,   b) adding a complex according to  claim 7 ,   c) feeding in H 2  and CO,   d) heating the reaction mixture, wherein the olefin is converted to an aldehyde.   
     
     
         12 . Process comprising the following process steps:
 a) initially charging an olefin,   b) adding a compound according to  claim 1  and a substance including a metal selected from: Rh, Ru, Co, Ir,   c) feeding in H 2  and CO,   d) heating the reaction mixture, wherein the olefin is converted to an aldehyde.   
     
     
         13 . Complex according to  claim 8 ,
 where M=Rh.