Diaryl alkylphosphonates and methods for preparing same

Abstract

A method for preparing substantially pure optionally substituted diaryl alkylphosphonates from an optionally substituted triarylphosphite and an optionally substituted trialkylphosphite or an optionally substituted alkanol under special reaction conditions is described.

1 - 30 . (canceled) 
     
     
         31 . A catalyst for making diaryl alkylphosphonate comprising at least one optionally substituted triarylphosphite combined with at least one alkylating catalyst. 
     
     
         32 . The catalyst of  claim 31 , wherein the alkylating catalyst is an alkyl halide of general formula (VII):
   R 10 —X  (VII)
   wherein R 10  is C 1 -C 20  alkyl; and   X is a halide.   
     
     
         33 . The catalyst of  claim 31 , having the general formula (VI): 
       
         
           
           
               
               
           
         
         wherein R 1  is of general formula (II): 
       
       
         
           
           
               
               
           
         
       
       wherein R 3 , R 4 , R 5 , R 6 , and R 7 , independently, are selected from hydrogen, trifluoromethyl, nitro, cyano, C 1 -C 20  alkyl, an aromatic, a halide, C 1 -C 20  alkyl ether, benzyl halide, benzylether, aromatic ether and combinations thereof.
 R 10  is C 1 -C 20  alkyl; and 
 X is a halide. 
 
     
     
         34 . The catalyst of  claim 33 , wherein the halide is selected from the group consisting of F, Cl, Br, or I. 
     
     
         35 . The catalyst of  claim 31 , wherein the catalyst is stable at ambient temperature without loss of catalytic activity. 
     
     
         36 . The catalyst of  claim 31 , wherein the catalyst is stable when heated to a temperature up to about 260° C. without loss of catalytic activity. 
     
     
         37 . A method for preparing a catalyst comprising combining at least one optionally substituted triarylphosphite and at least one alkylating catalyst. 
     
     
         38 . The method of  claim 37 , wherein the catalyst is of general formula (VI): 
       
         
           
           
               
               
           
         
         wherein R 1  is of general formula (II): 
       
       
         
           
           
               
               
           
         
       
       wherein R 3 , R 4 , R 5 , R 6 , and R 7 , independently, are selected from hydrogen, trifluoromethyl, nitro, cyano, C 1 -C 20  alkyl, an aromatic, a halide, C 1 -C 20  alkyl ether, benzyl halide, benzylether, aromatic ether and combinations thereof
 R 10  is C 1 -C 20  alkyl; and 
 X is a halide. 
 
     
     
         39 . The method of  claim 37 , wherein the least one optionally substituted triarylphosphite does not undergo an Arbuzov reaction. 
     
     
         40 . A method for preparing an optionally substituted diaryl alkylphosphonate comprising:
 heating a catalyst of general formula general formula (VI):   
       
         
           
           
               
               
           
         
       
       wherein R 1  is of general formula (II): 
       
         
           
           
               
               
           
         
       
       wherein R 3 , R 4 , R 5 , R 6 , and R 7 , independently, are selected from hydrogen, trifluoromethyl, nitro, cyano, C 1 -C 20  alkyl, an aromatic, a halide, C 1 -C 20  alkyl ether, benzyl halide, benzylether, aromatic ether and combinations thereof
 R 10  is C 1 -C 20  alkyl; and 
 X is a halide 
 
       to a defined reaction temperature of at least about 210° C.; and
 adding to the catalyst:
 (i) an optionally substituted trialkylphosphite in a molar excess of the catalyst; or 
 (ii) an optionally substituted alkanol in a molar excess of the catalyst; and 
 
 reacting the catalyst and optionally substituted trialkylphosphite or optionally substituted alkanol to form the optionally substituted diaryl alkylphosphonate wherein the optionally substituted diaryl alkylphosphonate contains substantially no triarylphosphite.