Method for preparing perfluorocarbon-substituted methanols

Abstract

Methods for producing perfluorocarbon monomethanols or dimethanols are disclosed. The methods of the invention can provide branched perfluorocarbon monomethanols or dimethanols with good purity and yields.

1 . A perfluorocarbon dimethanol compound represented by the formula R f —CF(CH 2 OH) 2 , wherein R f  is a perfluorocarbon moiety, wherein R f  may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof.  
   
   
       2 . The compound of  claim 1 , wherein R f  is a monovalent, perfluorinated, alkyl or alkenyl organic radical having one to twenty carbon atoms, wherein the radical can be interrupted by divalent oxygen or sulfur atoms and may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof.  
   
   
       3 . The compound of  claim 1 , wherein R f  is a perfluoroalkyl moiety, wherein R f  may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof.  
   
   
       4 . The compound of  claim 1 , wherein R f  is selected from the group consisting of trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl, 2-trifluoromethoxy perfluoropentyl, perfluorocyclopentyl, wherein R f  may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof.  
   
   
       5 . A method for preparing a perfluorocarbon dimethanol compound represented by the formula R f —CF(CH 2 OH) 2 , wherein R f  is a perfluorocarbon moiety, wherein R f  may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof, the method comprising: 
 reacting a perfluorocarbon diester of a perfluorocarbon dicarboxylic acid with a reducing reagent under reducing conditions, such that a perfluorocarbon methanol is prepared.    
   
   
       6 . The method of  claim 5 , wherein the perfluorocarbon diester of a perfluorocarbon dicarboxylic acid is represented by the formula R′ f O(O)C—C(R f )F—C(O)OR″ f , in which R′ f  and R″ f  are each independently a perfluorocarbon moiety which may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof.  
   
   
       7 . The method of  claim 5 , wherein the reducing reagent comprises a metal hydride.  
   
   
       8 . The method of  claim 5 , wherein the reducing reagent comprises a hydrogen source and a catalyst.  
   
   
       9 . The method of  claim 8 , wherin the catalyst is a noble metal catalyst.  
   
   
       10 . The method of  claim 9 , wherin the noble metal catalyst is selected from the group consisting of a platinum catalyst and a palladium catalyst.  
   
   
       11 . A compound of formula R f —CF(CH 2 OH) 2 , wherein R f  is a perfluorocarbon moiety, wherein R f  may be substituted by a halogen, hydroxyl, alkyl, alkoxyl, cyano, azido, heterocyclyl, aralkyl, aromatic, or heteroaromatic moiety, or perfluorinated derivatives thereof, prepared by the method comprising: 
 reacting a perfluorocarbon diester of a perfluorocarbon dicarboxylic acid with a reducing reagent under reducing conditions, such that a perfluorocarbon methanol is prepared.