Manufacture of conjugated linoleic salts and acids

Abstract

A process to manufacture conjugated linoleic acid (CLA)-containing materials such as conjugated linoleic salts and acids that are enriched in desirable cis-9, trans-11- and trans-10, cis-12-CLA isomers and are low in certain undesirable isomers. The process generally entails isomerization of an alkyl ester of a linoleic acid-containing material at a temperature typically between about 90 to 140° C. to effectuate conjugation of the double bonds, followed by saponification of the resultant CLA-containing fatty acid ester to produce a CLA-containing fatty acid salt, followed by neutralization of the CLA-containing fatty acid salt with an acid source to produce a CLA-containing fatty acid.

1 - 28  (canceled).  
     
     
         29 . A method for producing conjugated linoleic acid, comprising: 
 a) providing: 
 i) a composition comprising esters of linoleic acid; and  
 ii) an alcoholate catalyst;  
   b) treating said composition comprising esters of linoleic acid with said alcoholate catalyst to produce a conjugated linoleic acid ester composition;    c) treating said conjugated linoleic acid ester composition with alkali to produce a saponified conjugated linoleic acid composition; and    d) treating said saponified conjugated linoleic acid composition with a mild acid wash to produce a free conjugated fatty acid composition.    
     
     
         30 . The method of  claim 29 , wherein said mild acid wash is performed with a citric acid solution.  
     
     
         31 . The method of  claim 29 , wherein said composition comprising esters of linoleic acid is derived from an oil selected from the group consisting of safflower, sunflower, and corn oil.  
     
     
         32 . The method of  claim 29 , wherein said alcoholate catalyst is selected from the group consisting of sodium methylate, potassium methylate, sodium ethylate and potassium ethylate.  
     
     
         33 . The conjugated linoleic acid composition produced by the method of  claim 29 .  
     
     
         34 . A food product comprising the conjugated linoleic acid composition of  claim 33 .  
     
     
         35 . A capsule containing the conjugated linoleic acid composition of  claim 33 .  
     
     
         36 . A method of splitting saponified conjugated linoleic acids comprising: 
 a) providing 
 i) a composition comprising saponified conjugated linoleic acid, and  
 ii) a mild acid solution; and  
   b) washing said composition comprising saponified conjugated linoleic acid with said mild acid solution to produce a composition comprising free conjugated linoleic acid.    
     
     
         37 . The conjugated linoleic acid composition produced by the method of  claim 36 .  
     
     
         38 . A food product comprising the conjugated linoleic acid composition of  claim 37 .  
     
     
         39 . A capsule containing the conjugated linoleic acid composition of  claim 37 .  
     
     
         40 . A method for producing conjugated linoleic acid comprising: 
 a) providing: 
 i) a composition comprising esters of linoleic acid; and  
 ii) an alcoholate catalyst;  
   b) treating said composition comprising esters of linoleic acid with said alcoholate catalyst to produce a conjugated linoleic acid ester composition;    c) treating said conjugated linoleic acid ester composition with alkali to produce a saponified conjugated linoleic acid composition comprising residual alcohol;    d) removing said ethanol from said saponified conjugated linoleic acid composition; and    e) treating said saponified conjugated linoleic acid composition with an acid solution to produce a free conjugated fatty acid composition.    
     
     
         41 . The method of  claim 40 , wherein said composition comprising esters of linoleic acid is derived from an oil selected from the group consisting of safflower, sunflower, and corn oil.  
     
     
         42 . The method of  claim 40 , wherein said alcoholate catalyst is selected from the group consisting of sodium methylate, potassium methylate, sodium ethylate and potassium ethylate.  
     
     
         43 . The conjugated linoleic acid composition produced by the method of  claim 40 .  
     
     
         44 . A food product comprising the conjugated linoleic acid composition of  claim 43 .  
     
     
         45 . A capsule containing the conjugated linoleic acid composition of  claim 43 .  
     
     
         46 . A method for producing conjugated linoleic acid, comprising: 
 a) providing a composition containing alkyl esters of linoleic acid and an alcoholate catalyst;    b) isomerizing said composition containing alkyl esters of linoleic acid with said alcoholate catalyst to produce a conjugated linoleic acid ester composition;    c) saponifying said conjugated linoleic acid ester composition with an inorganic or alkyl ammonium hydroxide to produce a saponified conjugated linoleic acid composition; and    d) neutralizing said saponified conjugated linoleic acid composition with an acid source to produce a free conjugated fatty acid composition.    
     
     
         47 . The method of  claim 46 , wherein said step (d) is performed with a citric acid.  
     
     
         48 . The method of  claim 46 , wherein said composition containing alkyl esters of linoleic acid is derived from an oil selected from the group consisting of safflower, sunflower, and corn oil.  
     
     
         49 . The method of  claim 46 , wherein said alcoholate catalyst is an alkali alkoxide salt of a C 1 -C 4  alkyl group alcohol.  
     
     
         50 . The conjugated linoleic acid composition produced by the method of  claim 46 .  
     
     
         51 . The conjugated linoleic acid composition of  claim 50 , wherein said composition comprises greater than 95 percent of a mixture of t10,c12 and c9, t11 fatty acid isomers  
     
     
         52 . A food product comprising the conjugated linoleic acid composition of  claim 50 .  
     
     
         53 . A capsule containing the conjugated linoleic acid composition of  claim 50 .  
     
     
         54 . A method of neutralizing saponified conjugated linoleic acids comprising: 
 a) providing a composition containing saponified conjugated linoleic acid, and a citric acid; and    b) neutralizing said composition containing said saponified conjugated linoleic acid with said citric acid solution to produce a composition containing free conjugated linoleic acid.    
     
     
         55 . The conjugated linoleic acid composition produced by the method of  claim 54 .  
     
     
         56 . The conjugated linoleic acid composition of  claim 55 , wherein said composition comprises greater than 95 percent of a mixture of t10,c12 and c9, t11 fatty acid isomers.  
     
     
         57 . A food product comprising the conjugated linoleic acid composition of  claim 55 .  
     
     
         58 . A capsule containing the conjugated linoleic acid composition of  claim 55 .  
     
     
         59 . A method for producing conjugated linoleic acid comprising: 
 a) providing a composition containing alkyl esters of linoleic acid and an alcoholate catalyst;    b) isomerizing said composition containing alkyl esters of linoleic acid with said alcoholate catalyst to produce a conjugated linoleic acid ester composition;    c) saponifying said conjugated linoleic acid ester composition with an inorganic or alkyl ammonium hydroxide to produce a saponified conjugated linoleic acid composition;    d) isolating saponified conjugated linoleic acids from said saponified conjugated linoleic acid composition; and    e) neutralizing said saponified conjugated linoleic acids with an acid source to produce a free conjugated fatty acid composition.    
     
     
         60 . The method of  claim 59 , wherein said composition containing alkyl esters of linoleic acid is derived from an oil selected from the group consisting of safflower, sunflower, and corn oil.  
     
     
         61 . The method of  claim 59 , wherein said alcoholate catalyst is an alkali alkoxide salt of a C 1 -C 4  alkyl group alcohol.  
     
     
         62 . The conjugated linoleic acid composition produced by the method of  claim 59 .  
     
     
         63 . The conjugated linoleic acid composition of  claim 62 , wherein said composition comprises greater than 95 percent of a mixture of t10,c12 and c9, t11 fatty acid isomers.  
     
     
         64 . A food product comprising the conjugated linoleic acid composition of  claim 62 .  
     
     
         65 . A capsule containing the conjugated linoleic acid composition of  claim 62.