Betaine esters and process for making and using

Abstract

A variety of betaine esters, including dialkylaminoalkyl cocoate betaines and dialkylaminoalkyl hydrogenated cocoate betaines are disclosed. These betaines can be advantageously prepared in high yield and purity by a three-step transiterification chemoenzymatic process or a two-step direct esterficiation chemoenzymatic process. These betaine esters have excellent surfactant properties.

We claim: 
     
         1 . A compound represented by the general formula 1: 
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of C 5 -C 17  alkyl and mixtures thereof; 
         R 1  is methyl and R 2  is selected from the group consisting of C 1 -C 5  alkyl; and 
         A is selected from the group consisting of C 3 -C 10  alkylene and C 3 -C 10  alkenylene. 
       
     
     
         2 . The compound according to  claim 1 , wherein A is selected from the group consisting of C 3 -C 8  alkylene and C 3 -C 8  alkenylene. 
     
     
         3 . The compound according to  claim 1 , wherein R 2  is methyl. 
     
     
         4 . The compound according to  claim 1 , wherein R is selected from the group consisting of C 5 -C 17  alkyl and mixtures thereof, R 2  is methyl, and A is 1,3-propylene. 
     
     
         5 . The compound according to  claim 1  wherein the compound is selected from the group consisting of 3-dimethylaminopropyl hydrogenated cocoate (R is a mixture of C 5 -C 17 ) betaine, 3-dimethylaminopropyl hydrogenated stripped cocoate (R is a mixture of C 9 -C 17 ) betaine, 3-dimethylaminopropyl laurate betaine, 3-dimethylaminopropyl myristate betaine, and 3-dimethylaminopropyl palmitate betaine. 
     
     
         6 . A surfactant comprising the compound according to  claim 1 . 
     
     
         7 . A formulated product comprising a compound according to  claim 1 . 
     
     
         8 . The product according to  claim 6 , wherein said compound is present in an amount of from about 0.001 weight % to about 20 weight %. 
     
     
         9 . The product according to  claim 7 , wherein the compound is present in an amount of from about 0.01 weight % to about 15 weight %. 
     
     
         10 . A method for the preparation of a betaine represented by general formula 1, 
       
         
           
           
               
               
           
         
         comprising: 
         a) producing an ester of formula 2: 
       
       
         
           
           
               
               
           
         
         wherein R is selected from the group consisting of C 5 -C 17  alkyl, C 5 -C 17  alkenyl, C 5 -C 17  dienyl, C 5 -C 17  trienyl, and mixtures thereof and R 6  is a C 1 -C 6  alkyl; 
         b) reacting a dialkylamino alcohol 3: 
       
       
         
           
           
               
               
           
         
       
       With ester 2 in the presence of an enzyme to form an intermediate 4: 
       
         
           
           
               
               
           
         
         wherein R 1  is methyl and R 2  is selected from the group consisting of C 1 -C 5  alkyl; 
         A is selected from the group consisting of C 3 -C 10  alkylene and C 3 -C 10  alkenylene, and 
         c) reacting intermediate 4 with sodium chloroacetate to produce a betaine. 
       
     
     
         11 . The method according to  claim 10 , wherein R is selected from the group consisting of C 5 -C 17  alkyl and mixtures thereof, R 1  is methyl, R 2  is selected from the group consisting of C 1 -C 5  alkyl, and A is selected from the group consisting of C 3 -C 8  alkylene and C 3 -C 8  alkenylene. 
     
     
         12 . The method according to  claim 10 , wherein the ester is produced by solvolysis of non-hydrogenated or hydrogenated triglycerides in the presence of a lower alcohol and a base, acid or enzyme catalyst. 
     
     
         13 . The method according to  claim 12 , wherein the lower alcohol is a C 1 -C 4  alcohol, R 2  is methyl, and A is selected from the group consisting of C 3 -C 8  divalent alkylene and C 3 -C 8  alkenylene. 
     
     
         14 . The method according to  claim 13 , wherein the lower alcohol is selected from the group consisting of methanol, ethanol, 1-propanol and 2-propanol, and A is 1,3-propylene. 
     
     
         15 . The method according to  claim 10 , wherein the enzyme is a protease, a lipase, or an esterase. 
     
     
         16 . A method for the preparation of a betaine represented by general formula 1, 
       
         
           
           
               
               
           
         
         comprising: 
         a) reacting a carboxylic acid 
       
       
         
           
           
               
               
           
         
         wherein R selected from the group consisting of C 5 -C 17  alkyl, C 5 -C 17  alkenyl, C 5 -C 17  dienyl, C 5 -C 17  trienyl, and mixtures thereof 
       
       with a dialkylamino alcohol 3: 
       
         
           
           
               
               
           
         
       
       in the presence of an enzyme to form an intermediate 4: 
       
         
           
           
               
               
           
         
         wherein R 1  is methyl and R 2  is selected from the group consisting of C 1 -C 5  alkyl; 
         A is selected from the group consisting of C 3 -C 10  alkylene and C 3 -C 10  alkenylene; and 
         b) reacting intermediate 4 with sodium chloroacetate to produce a betaine. 
       
     
     
         17 . The method according to  claim 16 , wherein R is selected from the group consisting of C 5 -C 17  alkyl, R 1  is methyl, R 2  is selected from the group consisting of C 1 -C 5  alkyl, and A is selected from the group consisting of C 3 -C 8  alkylene and C 3 -C 8  alkenylene. 
     
     
         18 . The method according to  claim 16 , wherein, R 2  is methyl, and A is selected from the group consisting of C 3 -C 8  divalent alkylene and C 3 -C 8  alkenylene. 
     
     
         19 . The method according to  claim 18 , wherein A is 1,3-propylene. 
     
     
         20 . The method according to  claim 16 , wherein the enzyme is a protease, a lipase, or an esterase.