Process for synthesis of fluorinated olefins

Abstract

wherein X1, X2, and X3 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, provided that X1 and X2 in formula (I) are not both hydrogen and Z is Cl, I, Br, or F.

What is claimed is: 
     
         1 . A process for the synthesis of 2-halo-3,3,3-fluoropropene comprising:
 (a) reacting a compound of formula (I)
   X 1 X 2   (I)
 
   
       with a compound of formula (II)
   CX 1 X 2 X 3 CX 1 ═CX 1 X 2   (II)
 
 
       to produce a reaction product comprising a compound of formula (III)
   CF 3 CHX 1 CH 2 X 2   (III), and
 
 (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound of formula (III) to a compound of formula (IV)
   CF 3 CZ═CH 2   (IV).
 
 
 
       wherein X 1 , X 2 , and X 3  are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, provided that X 1  and X 2  in formula (I) are not both hydrogen and that Z is Cl, I, Br, or F. 
     
     
         2 . The process of  claim 1 , wherein compound of formula (IIIB) is CF 3 CHFCH 2 Cl. 
     
     
         3 . The process of  claim 1 , wherein compound of formula (IIIB) is CF 3 CHFCH 2 F. 
     
     
         4 . The process of  claim 1  wherein said reacting step (a) is a catalyzed liquid phase reaction. 
     
     
         5 . The process of  claim 4  wherein said reaction step (a) comprises reacting said HF with said compound of formula (IIA) at a temperature of from about 0° C. to about 250° C. and at a pressure of about 500 to about 1000 psig in the presence of a catalyst. 
     
     
         6 . The process of  claim 5  wherein said catalyst comprises SbCl 5 . 
     
     
         7 . The process of  claim 1  wherein said exposing step (b) is a liquid phase reaction that involves contacting the compound of formula (III) with a potassium hydroxide solution and, optionally, a Crown ether. 
     
     
         8 . The process of  claim 7  wherein said exposing step is at least partially conducted at a temperature of from about 25° C. to about 90° C. and at a pressure of about 100 to about 200 psig. 
     
     
         9 . The process of  claim 1  wherein said exposing step (b) is a vapor phase reaction that involves contacting the compound of formula (III) with a metal-based catalyst. 
     
     
         10 . The process of  claim 9  wherein said metal-based catalyst is at least one of Pd or Ni on a carbon substrate. 
     
     
         11 . The process of  claim 10  wherein said exposing step is at least partially conducted at a temperature of from about 200° C. to about 500° C. 
     
     
         12 . A process for the synthesis of 2,3,3,3 tetrafluoropropene comprising:
 (a) reacting a compound of formula (IA)
   X 1 X 2   (IA)
 
   
       with a compound of formula (IIA)
   CH 2 X 2 CX 2 ═CX 2 X 2   (IIA)
 
 
       to produce a reaction product comprising a compound of formula (IIIA)
   CF 3 CHFCH 2 Cl  (IIIC), and
 
 (b) exposing said compound of formula (IIIC) to reaction conditions effective to convert said compound of formula (IIIC) to a compound of formula (IVA)
   CF 3 CF═CH 2   (IVA),
 
 
 
       wherein X 1  is selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, and each X 2  is each independently selected from the group consisting of chlorine, bromine, fluorine and iodine. 
     
     
         13 . A process for the synthesis of 2,3,3,3 tetrafluoropropene comprising:
 (a) reacting a compound of formula (IA)
   X 1 X 2   (IA)
 
   
       with a compound of formula (IIA)
   CH 2 X 2 CX 2 ═CX 2 X 2   (IIA)
 
 
       to produce a reaction product comprising a compound of formula (IIID)
   CF 3 CHFCH 2 F  (IIID), and
 
 (b) exposing said compound of formula (IIID) to reaction conditions effective to convert said compound of formula (IIID) to a compound of formula (IVA)
   CF 3 CF═CH 2   (IVA),
 
 
 
       wherein X 1  is selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, and each X 2  is each independently selected from the group consisting of chlorine, bromine, fluorine and iodine.