Method for producing difluoroethylene

Patent metadata

Field	Value
Publication number	US-11247951-B2
Application number	US-202117161910-A
Country	US
Kind code	B2
Filing date	Jan 29, 2021
Priority date	Jun 13, 2018
Publication date	Feb 15, 2022
Grant date	Feb 15, 2022

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.

First claim

The invention claimed is:

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 metal catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z).

2. 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 metal catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z).

3. The production method according to claim 1 ,
wherein
the reaction product obtained in step (1) 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) 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.

4. The production method according to claim 1 , 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).

5. 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 metal 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 metal 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.

6. 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 metal 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.

7. The production method according to claim 1 , wherein the metal catalyst used in step (1) 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.

8. The production method according to claim 1 , wherein the metal catalyst used in step (1) comprises a fluorinated chromium oxide.

9. The production method according to claim 1 , wherein step (1) is performed at 200° C. to 400° C.

10. The production method according to claim 1 , wherein step (1) is performed in the presence of a diluent gas.

11. The production method according to claim 10 , wherein the diluent gas is at least one diluent gas selected from the group consisting of He, N 2 , Ar, HF, and O 2 .

Assignees

• Daikin Ind Ltd

Inventors

• Usui Takashi
• Nakaue Tsubasa
• Komatsu Yuzo
• Takahashi Kazuhiro
• Chaki Takehiro
• Kushida Megumi

Classifications

• C07C17/358 Primary

  by isomerisation · CPC title

• B01J37/26

  Fluorinating · CPC title

• C07B2200/09

  Geometrical isomers · CPC title

• B01J27/132

  with chromium, molybdenum, tungsten or polonium · CPC title

• C07C17/07

  by addition of hydrogen halides · CPC title