Novel alkyl perfluoroalkene ethers

Abstract

Disclosed are compositions comprising a compound having the formula CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , wherein R is CH 3 or C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3. Also disclosed are unsaturated fluoroethers selected from the group consisting of CF 3 (CF 2 ) x CF═CFCF(OR)(CF 2 ) y CF 3 , CF 3 (CF 2 ) x C(OR)═CFCF 2 (CF 2 ) y CF 3 , CF 3 CF═CFCF(OR)(CF 2 ) x (CF 2 ) y CF 3 , CF 3 (CF 2 ) x CF═C(OR)CF 2 (CF 2 ) y CF 3 , and mixtures thereof, wherein R can be either CH 3 , C 2 H 5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3. Also disclosed herein are novel methods of making a composition comprising at least one of the compounds described.

1 . A process comprising:
 a. contacting a perfluorinated olefin with an alcohol, an alkali metal hydroxide and water for a period of time to produce a reaction product mixture;   b. separating said reaction product mixture into an organic phase and an aqueous phase; and   c. isolating a mixture of perfluoroalkene ethers from said organic phase.   
     
     
         2 . The process of  claim 1 , wherein the perfluorinated olefin is perfluoro-3-heptene, pefluoro-2-heptene, perfluoro-2-hexene, perfluoro-3-hexene, perfluoro-2-pentene, or perfluoro-2-octene. 
     
     
         3 . The process of  claim 1 , further comprising adding a phase transfer catalyst. 
     
     
         4 . The process of  claim 3 , wherein said phase transfer catalyst is selected from the group consisting of crown ethers, onium salts, cryptates and polyalkylene glycols and derivatives thereof, and mixtures thereof. 
     
     
         5 . The process of  claim 3 , wherein said phase transfer catalyst is methyltrioctylammonium chloride. 
     
     
         6 . The process of  claim 1 , wherein said alcohol is methanol or ethanol. 
     
     
         7 . The process of  claim 1 , wherein said alkali metal hydroxide is sodium hydroxide or potassium hydroxide. 
     
     
         8 . The process of  claim 1 , wherein at least 90% of the fluorinated ethers produced are unsaturated. 
     
     
         9 . The process of  claim 1 , wherein at least 93% of the fluorinated ethers produced are unsaturated. 
     
     
         10 . The process of  claim 1 , wherein at least 96% of the fluorinated ethers produced are unsaturated.