Method for producing fluorinated organic compounds

Abstract

Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF═CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2═CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl═CH2, preferably in a 80-96% selectivity. The CF3CCl═CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl═CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.

What is claimed is: 
     
         1 . A method for producing fluorinated organic compounds comprising converting at least one compound of Formula (I)
   C(X) m CCl(Y) n C(X) m   (I)
   to at least one compound of Formula (II)
   CF 3 CF═CHZ  (II)
 
   where each X, Y and Z is independently H, F, Cl, I or Br, and each m is independently 1, 2 or 3, and n is 0 or 1.   
     
     
         2 . The method of  claim 1  wherein said converting step is a direct converting step. 
     
     
         3 . The method of  claim 1  wherein said converting step is an indirect converting step. 
     
     
         4 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound wherein n is 0, each X is independently H or Cl, and Z is H. 
     
     
         5 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound Formula (IA):
   C(X) 2 ═CClC(X) 3   (IA)
 
 wherein X is as identified in  claim 1 . 
 
     
     
         6 . The method of  claim 5  wherein Z in said compound of Formula (II) is H. 
     
     
         7 . The method of  claim 5  wherein X is independently H or Cl. 
     
     
         8 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises at least one tetrachloropropene. 
     
     
         9 . The method of  claim 5  wherein said at least one compound of Formula (IA) comprises at least one tetrachloropropene. 
     
     
         10 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises CH 2 ═CClCCl 3 . 
     
     
         11 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises CCl 2 ═CClCH 2 Cl. 
     
     
         12 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises CHCl═CClCCl 2 H. 
     
     
         13 . The method of  claim 1  wherein said at least one compound of Formula (I) is selected from the group consisting of CH 2 ═CClCCl 3 , CCl2═CClCH 2 Cl, CHCl═CClCCl 2 H, and combinations of these. 
     
     
         14 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound wherein n is 0 and the terminal saturated carbon has three (3) F substituents. 
     
     
         15 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound Formula (IAA):
   C(X) 2 ═CClCF 3   (IAA)
 
 wherein X is as identified in  claim 1 . 
 
     
     
         16 . The method of  claim 1  wherein each X in said compound of Formula (IAA) is independently H or Cl. 
     
     
         17 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises at least one trifluoropropene. 
     
     
         18 . The method of  claim 17  wherein said at least one trifluoropropene comprises CH 2 ═CClCF 3  (HCFC-1223xf). 
     
     
         19 . The method of  claim 1  wherein said at least one compound of Formula (I) comprises a compound of Formula (IB):
   C(X) 3 CClYC(X) 3   (IB)
 
 wherein X and Y are as identified in  claim 1 . 
 
     
     
         20 . The method of  claim 19  wherein each X in said compound of Formula (IB) is independently H or Cl.