Method for producing hexafluoro-1,3-butadiene

Patent metadata

Field	Value
Publication number	US-11117850-B2
Application number	US-201917046037-A
Country	US
Kind code	B2
Filing date	Jun 3, 2019
Priority date	Jun 22, 2018
Publication date	Sep 14, 2021
Grant date	Sep 14, 2021

Abstract

Provided is a method for producing hexafluoro-1,3-butadiene, and the method can produce hexafluoro-1,3-butadiene at an industrially sufficient level of yield. In a reaction liquid containing a halogenated butane represented by chemical formula, CF2X1—CFX2—CFX3—CF2X4 (X1, X2, X3, and X4 are each independently a halogen atom other than a fluorine atom), zinc, and an organic solvent, a reaction is conducted to eliminate the halogen atoms other than a fluorine atom, X1, X2, X3, and X4, from the halogenated butane, yielding hexafluoro-1,3-butadiene. During the reaction, the concentration of a zinc halide generated by the reaction, in the reaction liquid is not more than the solubility of the zinc halide in the organic solvent.

First claim

The invention claimed is:

1. A method for producing hexafluoro-1,3-butadiene, the method comprising:
conducting a reaction, in a reaction liquid containing a halogenated butane represented by chemical formula CF 2 X 1 -CFX 2 -CFX 3 -CF 2 X 4 (X 1 , X 2 , X 3 , and X 4 are each independently a chlorine atom, a bromine atom or an iodine atom), zinc, and an organic solvent selected from the group consisting of an alcohol, a cyclic ether, acetone, acetonitrile, an aromatic hydrocarbon, an amide solvent, an organic acid, and a mixed solvent thereof, to eliminate X 1 , X 2 , X 3 , and X 4 , which are selected from the group consisting of the chlorine atom, the bromine atom and the iodine atom, from the halogenated butane, yielding hexafluoro-1,3-butadiene, wherein
during the reaction, a concentration of a zinc halide generated by the reaction in the reaction liquid is not more than a solubility of the zinc halide in the organic solvent, and
as the reaction proceeds, an organic solvent is added to the reaction liquid to reduce the concentration of the zinc halide in the reaction liquid.

2. The method for producing hexafluoro-1,3-butadiene according to claim 1 , wherein the organic solvent is an alcohol.

3. The method for producing hexafluoro-1,3-butadiene according to claim 2 , wherein the alcohol is at least one of methanol, ethanol, 1-propanol, and 2-propanol.

4. The method for producing hexafluoro-1,3-butadiene according to claim 2 , wherein each of X 1 , X 2 , X 3 , and X 4 is a chlorine atom.

5. The method for producing hexafluoro-1,3-butadiene according to claim 3 , wherein each of X 1 , X 2 , X 3 , and X 4 is a chlorine atom.

6. The method for producing hexafluoro-1,3-butadiene according to claim 1 , wherein each of X 1 , X 2 , X 3 , and X 4 is a chlorine atom.

7. A method for producing hexafluoro-1,3-butadiene, the method comprising:
conducting a reaction, in a reaction liquid containing a halogenated butane represented by chemical formula CF 2 X 1 -CFX 2 -CFX 3 -CF 2 X 4 (X 1 , X 2 , X 3 , and X 4 are each independently a chlorine atom, a bromine atom or an iodine atom), zinc, and an organic solvent selected from the group consisting of an alcohol, a cyclic ether, acetone, acetonitrile, an aromatic hydrocarbon, an amide solvent, an organic acid, and a mixed solvent thereof, to eliminate X 1 , X 2 , X 3 , and X 4 , which are selected from the group consisting of the chlorine atom, the bromine atom and the iodine atom, from the halogenated butane, yielding hexafluoro-1,3-butadiene, wherein
during the reaction, a concentration of a zinc halide generated by the reaction in the reaction liquid is not more than a solubility of the zinc halide in the organic solvent, and
in the reaction, steps include:
extracting a portion of the reaction liquid to provide an extraction liquid as the extracted reaction liquid,
removing some or all of the dissolved zinc halide from the extraction liquid, and
returning the extraction liquid from which the zinc halide has been removed to the original reaction liquid to reduce the concentration of the zinc halide in the reaction liquid.

8. The method for producing hexafluoro-1,3-butadiene according to claim 7 , wherein the organic solvent is an alcohol.

9. The method for producing hexafluoro-1,3-butadiene according to claim 7 , wherein each of X 1 , X 2 , X 3 , and X 4 is a chlorine atom.

Assignees

• Showa Denko Kk

Inventors

• FUKUCHI Yohsuke
• OGURO Shinya
• Inoue Nozomi

Classifications

• C07C17/23 Primary

  by dehalogenation · CPC title

• C07C21/20

  Halogenated butadienes · CPC title

• B01J23/06

  of zinc, cadmium or mercury · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C21/19

  Halogenated dienes · CPC title