Optically enhanced chiral ionic liquids

Abstract

The invention relates to the use of optically enhanced chiral ionic liquids, particularly for gas chromatography and as a reaction solvent. Specific optically enhanced chiral cationic liquids are described as is a class of optically enhanced chiral anionic liquids.

1 . A chiral cation containing optically enhanced ionic liquid in which at least one enantiomer is enhanced by at least about 2%.  
   
   
       2 . The chiral cation containing optically enhanced ionic liquid of  claim 1  in which at least one enantiomer is enhanced by at least about 10%.  
   
   
       3 . The chiral cation containing optically enhanced ionic liquid of  claim 1  in which at least one enantiomer is enhanced by at least about 20%.  
   
   
       4 . The chiral cation containing optically enhanced ionic liquid of  claim 1  in which at least one enantiomer is substantially optically pure.  
   
   
       5 . The chiral cation containing optically enhanced ionic liquid of  claim 1  comprising only at least one enantiomerically pure enantiomer.  
   
   
       6 . A chiral anion containing optically enhanced ionic liquid which is not a lactate.  
   
   
       7 . The chiral anion containing optically enhanced ionic liquid of  claim 6  having a melting point of 100° C. or less.  
   
   
       8 . A chiral anion containing optically enhanced ionic liquid in which at least one enantiomer is enhanced by at least about 2%.  
   
   
       9 . The chiral anion containing optically enhanced ionic liquid of  claim 8  in which at least one enantiomer is enhanced by at least about 10%.  
   
   
       10 . The chiral anion containing optically enhanced ionic liquid of  claim 8  in which at least one enantiomer is enhanced by at least about 20%.  
   
   
       11 . The chiral anion containing optically enhanced ionic liquid of  claim 8  in which at least one enantiomer is substantially optically pure.  
   
   
       12 . The chiral cation containing optically enhanced ionic liquid of  claim 8  comprising only at least one enantiomerically pure enantiomer.  
   
   
       13 . The asymmetric synthesis of a compound comprising the steps of: conducting a chemical reaction on at least one reactant in the presence of an OCIL to produce a reaction product, and recovering said reaction product; wherein said reaction product is optically active and either only one enantiomer will be present or one enantiomer will be present in an amount which is greater than the other enantiomer of said reaction product.  
   
   
       14 . An asymmetric mixture of enantiomers produced in accordance with the process of  claim 13 .  
   
   
       15 . An enantiomerically pure enantiomer produced in accordance with the process of  claim 13 .  
   
   
       16 . A method for deracemization of a racemic compound comprising the steps of: conducting a chemical reaction on at least one racemic reactant in the presence of an OCIL, and producing a reaction product that is optically enhanced.  
   
   
       17 . An asymmetric mixture of enantiomers produced in accordance with the process of  claim 16 .  
   
   
       18 . An enantiomerically pure enantiomer produced in accordance with the process of  claim 16 .  
   
   
       19 . A chemical reaction comprising the steps of: mixing, dissolving, dispersing or suspending at least one first reactant in a substantially pure OCIL or in a solvent including a substantially pure OCIL and reacting said at least one first reactant with at least one second reactant, at least one catalyst or said OCIL so as to produce a reaction product which is changed in structure or properties when compared to said at least one first reactant.  
   
   
       20 . The chemical reaction of  claim 19  wherein said OCIL contains a chiral cation.  
   
   
       21 . The chemical reaction of  claim 19  wherein said OCIL contains a chiral anion.  
   
   
       22 . The reaction product produced in accordance with the process of  claim 19 .  
   
   
       23 . The reaction product produced in accordance with the process of  claim 20 .  
   
   
       24 . The reaction product produced in accordance with the process of  claim 21 .  
   
   
       25 . The reaction product produced in accordance with the process of  claim 19  wherein said reaction product is asymmetric.  
   
   
       26 . A column for use in chromatography comprising: a column and a stationary phase which is an OCIL associated therewith.  
   
   
       27 . The column of  claim 26  wherein said column is a capillary and said stationary phase is coated on an inner surface of said capillary.  
   
   
       28 . The column of  claim 26  wherein said stationary phase is absorbed, adsorbed or coated on a solid support which is packed into said column.  
   
   
       29 . A method of separating optical isomers comprising the steps of: mixing, dissolving, dispersing or suspending optical isomers in a mobile phase, introducing said optical isomers into a column that includes at least one OCIL as a stationary phase, and advancing said mobile phase and said optical isomers through said column so as to resolve at least one of said optical isomers.  
   
   
       30 . An OCIL having the following structure:  
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       31 . An optically enhanced chiral ionic liquid composed of at least one salt comprising both chiral anions and chiral cations.