Process for the production of vicinal diesters from epoxides

Abstract

The present invention relates to a process comprising the steps of reacting in the presence of an epoxide opening catalyst, a substituted epoxide, and preferably a silicone containing substituted epoxide with at least one carboxylic acid and at least one protecting agent to form a vicinal dialkyl ester or a vicinal disilyl ester.

1 . A process comprising the steps of reacting a substituted epoxide with at least one epoxide opening catalyst, at least one carboxylic acid, at least one protecting agent and at least one inhibitor at a temperature above about 60° C. for at least about 4 hours to form a compound of formula VI or VII:  
       
         
           
           
               
               
           
         
       
       wherein R 2  is selected from the group consisting of esters, amides, substituted and unsubstituted alkyls, siloxanes and ethers, R 5  is a straight or branched alkyl and alkenyl groups having 1 to 10 carbon atoms and R 6  is a residue of said protecting group which is capable of forming an ester or ether linkage.  
     
     
         2 . The process of  claim 1  wherein said substituted epoxide is a compound of Formula II  
       
         
           
           
               
               
           
         
       
       wherein R 2  is selected from the group consisting of esters, amides, substituted and unsubstituted alkyls, siloxanes and ethers.  
     
     
         3 . The process of  claim 2  wherein R 2  is selected from the group consisting of C1 to 3 alkyls substituted with at least one Si containing substitutent.  
     
     
         4 . The process of  claim 1  wherein said substituted epoxide is a compound of formula III:  
       
         
           
           
               
               
           
         
       
       wherein R 3  and R 4  are independently selected from alkyl groups having 1 to 3 carbon atoms, n is 1 to 3 and x is 0 to 3.  
     
     
         5 . The process of  claim 1  wherein said protecting agent is selected from the group consisting of anhydrides, trimethylsilylchloride and allyl halide.  
     
     
         6 . The process of  claim 5  wherein said protecting agent is an anhydride having the formula R 5 CO 2 OCR 5 , wherein R 5  may be the same or different, and is selected from the group consisting of straight or branched alkyl and alkenyl groups having 1 to 10 carbon atoms.  
     
     
         7 . The process of  claim 5  wherein R 5  is selected from alkenyl groups having 1-5 carbon atoms.  
     
     
         8 . The process of  claim 5  wherein R 5  is selected from vinyl, styryl and allyl.  
     
     
         9 . The process of  claim 1  wherein said carboxylic acid R 5 CO 2 H, wherein R 5  is selected from the group consisting of straight or branched alkyl and alkenyl groups having 1 to 10 carbon atoms.  
     
     
         10 . The process of  claim 9  wherein R 5  is selected from alkenyl groups having 1-5 carbon atoms.  
     
     
         11 . The process of  claim 9  wherein R 5  is selected from vinyl, styryl and allyl.  
     
     
         12 . The process of  claim 1  wherein said epoxide opening catalyst is selected from the group consisting of Lewis acids, Lewis bases, Bronsted acids and porphyrin complexes.  
     
     
         13 . The process of  claim 1  wherein said epoxide opening catalyst comprises an alkali metal salt.  
     
     
         14 - 24 . (canceled)  
     
     
         25 . The process of  claim 1 , further comprising the step of purifying the compound of Forumula VI or VII by supercritical fluid extraction.