Method for producing fluorohalogenated hydrocarbon

Patent metadata

Field	Value
Publication number	US-11034634-B2
Application number	US-201816481300-A
Country	US
Kind code	B2
Filing date	Jan 31, 2018
Priority date	Jan 31, 2017
Publication date	Jun 15, 2021
Grant date	Jun 15, 2021

Abstract

A method for producing a fluorine-containing halogenated hydrocarbon comprising reacting a chlorine-containing compound and hydrogen fluoride in a vapor phase, and a separation step of separating a reaction product containing hydrogen fluoride, hydrogen chloride, and organic matter containing the fluorine-containing halogenated hydrocarbon into multiple components, the separation step comprising: separating the reaction product into a gas phase and a liquid phase, increasing the pressure of the liquid phase and supplying the liquid phase into a distillation column, compressing the gas phase and supplying the gas phase into the distillation column, separating a first stream containing the hydrogen chloride from the top of the distillation column, and separating a second stream containing the organic matter and the hydrogen fluoride from the bottom of the distillation column. The method is for stably obtaining a target compound by preventing hydrogen fluoride contained in the outlet gas from condensing during compression.

First claim

The invention claimed is:

1. A method for producing a fluorine-containing halogenated hydrocarbon comprising the step of reacting a chlorine-containing compound and hydrogen fluoride in a vapor phase,
the method comprising a separation step of separating a reaction product containing hydrogen fluoride, hydrogen chloride, and organic matter containing the fluorine-containing halogenated hydrocarbon into multiple components,
the fluorine-containing halogenated hydrocarbon being at least one member selected from the group consisting of 1,1,1,2,2-pentafluoropropane (HFC-245cb), 1,1,1,3,3-pentafluoropropane (HFC-245fa), E,Z-1,3,3,3-tetrafluoropropene (E,Z-HFO-1234ze), 2,3,3,3-tetrafluoropropene (HFO-1234yf), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), and 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd),
the separation step comprising:

(1) step 1 of separating the reaction product into a gas phase and a liquid phase,
(2) step 2 of increasing the pressure of the liquid phase and supplying the liquid phase into a distillation column A,
(3) step 3 of compressing the gas phase and supplying the gas phase into the distillation column A, and
(4) step 4 of separating a first stream containing the hydrogen chloride from the top of the distillation column A, and separating a second stream containing the organic matter and the hydrogen fluoride from the bottom of the distillation column A,
(5) in step 3, the gas phase being compressed in series in two or more stages using a compressor, and heated by a heater to maintain a fraction of compressed gas in each stage at 1.

2. The method according to claim 1 , wherein the chlorine-containing compound is at least one member of chlorine-containing alkanes or chlorine-containing alkenes.

3. The method according to claim 1 , wherein the chlorine-containing compound is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane (HCC-240db), 1,1,2,2,3-pentachloropropane (HCC-240aa), 1,1,2,3-tetrachloropropene (HCO-1230xa), 2,3,3,3-tetrachloropropene (HCO-1230xf), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf), 1,2,3-trichloro-1,1-difluoropropane (HCFC-242dc), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), 2,3-dichloro-1,1,1-trifluoropropane (HCFC-243db), 3,3-dichloro-1,1,1-trifluoropropane (HCFC-243fa), 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), and 3-chloro-1,1,1,3-tetrafluoropropane (HCFC-244fa).

4. The method according to claim 1 , wherein the fluorine-containing halogenated hydrocarbon comprises HFO-1234yf, and the chlorine-containing compound is at least one member selected from the group consisting of 1,1,1,2,3-pentachloropropane (HCC-240db), 1,1,2,2,3-pentachloropropane (HCC-240aa), 1,1,2,3-tetrachloropropene (HCO-1230xa), 2,3,3,3-tetrachloropropene (HCO-1230xf), 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), 2,3-dichloro-3,3-difluoropropene (HCFO-1232xf), 1,2,3-trichloro-1,1-difluoropropane (HCFC-242dc), 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd), and 2,3-dichloro-1,1,1-trifluoropropane (HCFC-243db).

5. The method according to claim 1 , wherein the fluorine-containing halogenated hydrocarbon comprises HFO-1234yf, and the chlorine-containing compound comprises HCFO-1233xf.

6. The method according to claim 1 , wherein the molar ratio of the hydrogen fluoride to the chlorine-containing compound at the beginning of the reaction of the chlorine-containing compound and the hydrogen fluoride in a vapor phase is 10 or more.

7. The method according to claim 1 , wherein when the gas phase is compressed in series in two or more stages in step 3, the compression rate at each stage is 2 times or more.

8. The method according to claim 1 , further comprising the step of supplying the second stream into a distillation column B, and separating the second stream into a third stream containing the fluorine-containing halogenated hydrocarbon and a fourth stream containing the hydrogen fluoride and organic matter other than the fluorine-containing halogenated hydrocarbon by distillation.

Assignees

• Daikin Ind Ltd

Inventors

• Takahashi Kazuhiro
• Takakuwa Tatsuya

Classifications

• C07C17/383 Primary

  by distillation · CPC title

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C19/08

  containing fluorine · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title