Method for producing difluoroethylene

Abstract

The present invention aims to provide an efficient method for obtaining a desired isomer of HFO-1132 from a composition comprising trans-1,2-difluoroethylene (HFO-1132(E)) and cis-1,2-difluoroethylene (HFO-1132(Z)). The present invention provides, as a means for solving the problem, a method for producing HFO-1132(E) and/or HFO-1132(Z), comprising steps (1) to (3): (1) supplying a composition comprising HFO-1132(E) and/or HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z); (2) separating the reaction product obtained in step (1) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and (3) recycling the first stream or the second stream obtained in step (2) to the reactor, to subject the first stream or the second stream to the isomerization reaction.

1 . A method for producing trans-1,2-difluoroethylene (HFO-1132(E)) and/or cis-1,2-difluoroethylene (HFO-1132(Z)), comprising the step of:
 (1) supplying a composition comprising HFO-1132(E) and/or HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z).   
     
     
         2 . A method for producing cis-1,2-difluoroethylene (HFO-1132(Z)), comprising the step of:
 (1A) supplying trans-1,2-difluoroethylene (HFO-1132(E)) or a composition comprising HFO-1132(E) and HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z).   
     
     
         3 . A method for producing HFO-1132(E), comprising the step of:
 (1B) supplying HFO-1132(Z) or a composition comprising HFO-1132(E) and HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z).   
     
     
         4 . The production method according to any one of  claims 1  to  3 ,
 wherein
 the reaction product obtained in step (1), (1A), or (1B) comprises HFO-1132(E) and HFO-1132(Z), and 
 the method further comprises steps (2) and (3): 
 
 (2) separating the reaction product obtained in step (1), (1A), or (1B) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and 
 (3) recycling the first stream or the second stream obtained in step (2) to the reactor, to subject the first stream or the second stream to the isomerization reaction. 
 
     
     
         5 . The production method according to any one of  claims 1  to  4 , further comprising the step of:
 (i) subjecting a halogenated ethane to a dehydrohalogenation reaction or a dehalogenation reaction to obtain a composition comprising HFO-1132(E) and HFO-1132(Z), 
 wherein
 the composition comprising HFO-1132(E) and HFO-1132(Z) obtained in step (i) is used as the composition comprising HFO-1132(E) and HFO-1132(Z) in step (1), (1A), or (1B). 
 
 
     
     
         6 . A method for producing a composition comprising HFO-1132(E) and/or HFO-1132(Z), comprising steps (a) to (d):
 (a) supplying a composition comprising hydrogen fluoride and HFO-1132(E) and/or HFO-1132(Z) to a reactor R 1  filled with a catalyst to perform a fluorination reaction, thereby obtaining a reaction product comprising 1,1,2-trifluoroethane (HFC-143);   (b) supplying the reaction product obtained in step (a) to a reactor R 2  filled with a catalyst to perform a dehydrofluorination reaction, thereby obtaining a reaction product comprising HFO-1132(E) and/or HFO-1132(Z);   (c) separating the reaction product obtained in step (b) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and   (d) recycling the first stream or the second stream obtained in step (c) to the reactor R 1 , to subject the first stream or the second stream to the fluorination reaction.   
     
     
         7 . A method for producing a composition comprising HFO-1132(E) and/or HFO-1132(Z), comprising steps (x) to (z):
 (x) supplying HFC-143 and a composition comprising HFO-1132(E) and/or HFO-1132(Z) to a reactor filled with a catalyst to perform a dehydrofluorination reaction of the HFC-143 and an isomerization reaction of the HFO-1132(E) and the HFO-1132(Z), thereby obtaining a composition comprising the HFO-1132(E) and the HFO-1132(Z);   (y) separating the reaction product obtained in step (x) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and   (z) recycling the first stream or the second stream obtained in step (y) to step (x), to subject the first stream or the second stream to the isomerization reaction.   
     
     
         8 . The production method according to any one of  claims 1  to  7 , wherein the catalyst used in step (1), (1A), (1B), (b), or (x) comprises at least one compound selected from the group consisting of halides, oxides, and oxidized halides of at least one element selected from the group consisting of Al, Mg, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Zr, Nb, and Ta. 
     
     
         9 . The production method according to any one of  claims 1  to  8 , wherein the catalyst used in step (1), (1A), (1B), (b), or (x) comprises a fluorinated chromium oxide. 
     
     
         10 . The production method according to any one of  claims 1  to  9 , wherein steps (1), (1A), (1B), (b), and (x) are performed at 200° C. to 400° C. 
     
     
         11 . The production method according to any one of  claims 1  to  10 , wherein steps (1), (1A), (1B), (b), and (x) are performed in the presence of a diluent gas. 
     
     
         12 . The production method according to  claim 11 , wherein the diluent gas is at least one diluent gas selected from the group consisting of He, N 2 , Ar, HF, and O 2 .