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 —C(R′ f )(CH 2 OH) 2 , wherein R f  is a perfluorocarbon moiety, and R′ f  is fluoride or a perfluorocarbon moiety, wherein R′ f  and R f  may be independently 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 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.  
   
   
       3 . The compound of  claim 1 , wherein R′ f  is fluoride.  
   
   
       4 . 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.  
   
   
       5 . The compound of  claim 4 , 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.  
   
   
       6 . The compound of  claim 4 , 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.  
   
   
       7 . The compound of  claim 4 , 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.