Transition metal complex

Abstract

Disclosed is transition metal complex that serves as a catalytic component with which 1-hexene can be produced efficiently with excellent selectivity, even under high temperature conditions, by means of an ethylene trimerization reaction. Said transition metal complex is represented by the following general formula (1), wherein M 1 represents a Group 4 transition metal atom, and R 1 through R 11 and X 1 through X 3 each independently represent a hydrogen atom, a halogen atom, or a specific organic group.

1 . A transition metal complex represented by general formula (1): 
       
         
           
           
               
               
           
         
         wherein
 M 1  represents a transition metal atom of Group 4 of the Periodic Table of the Elements; R 1 , R 2 , R 3  and R 4  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an alkoxy group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryloxy group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyloxy group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20, or 
 a disubstituted amino group represented by —N(R 13 ) 2 , wherein the two R 13  groups each independently represent a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the two R 13  groups is 2 to 20, and 
 at least one of R 1 , R 2 , R 3  and R 4  is a halogen atom, the alkyl group, the alkoxy group, the aryl group, the aryloxy group, the aralkyl group, the aralkyloxy group, the substituted silyl group or the disubstituted amino group; 
 R 5  and R 9  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, or 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20; 
 R 6 , R 7  and R 8  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an alkoxy group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryloxy group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyloxy group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20, or 
 a disubstituted amino group represented by —N(R 13 ) 2 , wherein the two R 13  groups each independently represent a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the two R 13  groups is 2 to 20; 
 R 10  is a methyl group, and R 11  is 
 an alkyl group having 2 to 20 carbon atoms which optionally have a halogen atom as a substituent or 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent; 
 X 1 , X 2  and X 3  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an alkoxy group having 1 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aryloxy group having 6 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aralkyloxy group having 7 to 20 carbon atoms which may have a halogen atom as a substituent, 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20, or 
 a disubstituted amino group represented by —N(R 13 ) 2 , wherein the two R 13  groups each independently represent a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the two R 13  groups is 2 to 20; 
 of R 1 , R 2 , R 3  and R 4 , two groups bonded to two adjacent carbon atoms are optionally bonded to each other to form a ring together with the two carbon atoms to which the two groups are bonded; 
 of R 5 , R 6 , R 7 , R 8  and R 9 , two groups bonded to two adjacent carbon atoms are optionally bonded to each other to form a ring together with the two carbon atoms to which the two groups are bonded. 
 
       
     
     
         2 . The transition metal complex according to  claim 1 , wherein M 1  in the general formula (1) is a titanium atom. 
     
     
         3 . The transition metal complex according to  claim 2 , wherein each of R 1 , R 2 , R 3  and R 4  in the general formula (1) is a hydrogen atom, a halogen atom,
 an alkyl group having 1 to 20 carbon atoms which may have a halogen atom as a substituent,   an aryl group having 6 to 20 carbon atoms which may have a halogen atom as a substituent, or   an aralkyl group having 7 to 20 carbon atoms which may have a halogen atom as a substituent.   
     
     
         4 . The transition metal complex according to  claim 2 , wherein the cyclopentadienyl moiety represented by the general formula (2) in the general formula (1) 
       
         
           
           
               
               
           
         
         is selected from among methylcyclopentadienyl, ethylcyclopentadienyl, n-propylcyclopentadienyl, isopropylcyclopentadienyl, n-butylcyclopentadienyl, sec-butylcyclopentadienyl, tert-butylcyclopentadienyl, dimethylcyclopentadienyl, trimethylcyclopentadienyl, tetramethylcyclopentadienyl, phenylcyclopentadienyl, benzylcyclopentadienyl, indenyl, fluorenyl, tetrahydroindenyl, methyltetrahydroindenyl, dimethyltetrahydroindenyl, and octahydrofluorenyl. 
       
     
     
         5 . The transition metal complex according to  claim 2 , wherein each of R 1 , R 2 , R 3  and R 4  in the general formula (1) is a methyl group. 
     
     
         6 . A transition metal complex represented by general formula (1): 
       
         
           
           
               
               
           
         
         wherein
 M 1  represents a transition metal atom of Group 4 of the Periodic Table of the Elements; R 1 , R 2 , R 3  and R 4  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an alkoxy group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryloxy group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyloxy group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20, or 
 a disubstituted amino group represented by —N(R 13 ) 2 , wherein the two R 13  groups each independently represent a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the two R 13  groups is 2 to 20, and 
 at least one of R 1 , R 2 , R 3  and R 4  is a halogen atom, the alkyl group, the alkoxy group, the aryl group, the aryloxy group, the aralkyl group, the aralkyloxy group, the substituted silyl group or the disubstituted amino group; 
 R 5  and R 9  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, or 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20; 
 R 7  represents 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an alkoxy group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aryloxy group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 an aralkyloxy group having 7 to 20 carbon atoms which optionally have a halogen atom as a substituent, 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20, or 
 a disubstituted amino group represented by —N(R 13 ) 2 , wherein the two R 13  groups each independently represent a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the two R 13  groups is 2 to 20, and 
 R 6  and R 8  are each 
 an alkyl group having 1 to 20 carbon atoms which optionally have a halogen atom as a substituent or 
 an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent; 
 R 10  and R 11  each independently represent an aryl group having 6 to 20 carbon atoms which optionally have a halogen atom as a substituent; 
 X 1 , X 2  and X 3  each independently represent 
 a hydrogen atom, a halogen atom, 
 an alkyl group having 1 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an alkoxy group having 1 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aryl group having 6 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aryloxy group having 6 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aralkyl group having 7 to 20 carbon atoms which may have a halogen atom as a substituent, 
 an aralkyloxy group having 7 to 20 carbon atoms which may have a halogen atom as a substituent, 
 a substituted silyl group represented by —Si(R 12 ) 3 , wherein the three R 12  groups each independently represent a hydrogen atom, a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the three R 12  groups is 1 to 20, or 
 a disubstituted amino group represented by —N(R 13 ) 2 , wherein the two R 13  groups each independently represent a hydrocarbyl group or a halogenated hydrocarbyl group, and the total number of the carbon atoms in the two R 13  groups is 2 to 20; 
 of R 1 , R 2 , R 3  and R 4 , two groups bonded to two adjacent carbon atoms are optionally bonded to each other to form a ring together with the two carbon atoms to which the two groups are bonded; 
 of R 5 , R 6 , R 7 , R 8  and R 9 , two groups bonded to two adjacent carbon atoms are optionally bonded to each other to form a ring together with the two carbon atoms to which the two groups are bonded. 
 
       
     
     
         7 . The transition metal complex according to  claim 6 , wherein M 1  in the general formula (1) is a titanium atom. 
     
     
         8 . The transition metal complex according to  claim 7 , wherein each of R 1 , R 2 , R 3  and R 4  in the general formula (1) is a hydrogen atom, a halogen atom,
 an alkyl group having 1 to 20 carbon atoms which may have a halogen atom as a substituent,   an aryl group having 6 to 20 carbon atoms which may have a halogen atom as a substituent, or   an aralkyl group having 7 to 20 carbon atoms which may have a halogen atom as a substituent.   
     
     
         9 . The transition metal complex according to  claim 7 , wherein the cyclopentadienyl moiety represented by the general formula (2) in the general formula (1) 
       
         
           
           
               
               
           
         
         is selected from among methylcyclopentadienyl, ethylcyclopentadienyl, n-propylcyclopentadienyl, isopropylcyclopentadienyl, n-butylcyclopentadienyl, sec-butylcyclopentadienyl, tert-butylcyclopentadienyl, dimethylcyclopentadienyl, trimethylcyclopentadienyl, tetramethylcyclopentadienyl, phenylcyclopentadienyl, benzylcyclopentadienyl, indenyl, fluorenyl, tetrahydroindenyl, methyltetrahydroindenyl, dimethyltetrahydroindenyl, and octahydrofluorenyl. 
       
     
     
         10 . The transition metal complex according to  claim 7 , wherein each of R 1 , R 2 , R 3  and R 4  in the general formula (1) is a methyl group.