Methods for producing halogenated alkene compound and fluorinated alkyne compound

Patent metadata

Field	Value
Publication number	US-11655199-B2
Application number	US-202117407730-A
Country	US
Kind code	B2
Filing date	Aug 20, 2021
Priority date	Feb 21, 2019
Publication date	May 23, 2023
Grant date	May 23, 2023

Abstract

A halogenated alkene compound and a fluorinated alkyne compound are obtained at a high conversion rate and high selectivity by employing any of the following methods (1) to (4):(1) a halogenated butane compound represented by CX1X2X3CHX4CFHCX5X6X7, wherein X1, X2, X3, X4, X5, X6, and X7 are the same or different and each is a halogen atom, to a dehydrofluorination reaction;(2) a halogenated butene compound represented by CX1X2X3CX4═CHCX5X6X7, wherein X1, X2, X3, X4, X5, X6, and X7 are as defined above, to a dehydrohalogenation reaction;(3) a halogenated alkane compound represented by CHX8A1CHX9A2, wherein A1 and A2 are each a fluorine atom or a perfluoroalkyl group, and X8 and X9 are the same or different and each is a halogen atom, to a dehydrohalogenation reaction in the presence of a catalyst in a gas phase; and(4) a halogenated alkene compound represented by CX8A1=CHA2, wherein A1, A2, and X8 are as defined above, to a dehydrohalogenation reaction in the presence of a catalyst.

First claim

The invention claimed is:

1. A method for producing a composition containing a halogenated butene compound represented by formula (2A):
CX′X 2 X 3 CX 4 ═CHCX 5 X 6 X 7 (2A)

wherein X′, X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 are the same or different and each is a halogen atom, wherein, as the halogenated butene compound represented by formula (2A), an (E)-halogenated butene compound in an amount of 85.00 to 99.98 mol % is present based on the total amount of the composition, which is taken as 100 mol %,
the method comprising subjecting a halogenated butane compound represented by formula (1A):
CX 1 X 2 X 3 CHX 4 CFHCX 5 X 6 X 7 (1A)

wherein X′, X 2 , X 3 , X 4 , X 5 , X 6 , and X 7 are as defined above, to a dehydrofluorination reaction in a gas phase or a liquid phase,
wherein the dehydrofluorination reaction is performed in the presence of at least one catalyst selected from the group consisting of an activated carbon catalyst, a chromium oxide catalyst, and a silica alumina catalyst, when the dehydrofluorination reaction is performed in a gas phase.

2. The production method according to claim 1 , wherein the step of the dehydrofluorination reaction is performed in a liquid phase.

3. The production method according to claim 2 , wherein the step of the dehydrofluorination reaction is performed in the presence of a base.

4. The production method according to claim 2 , wherein the step of the dehydrofluorination reaction is performed in a closed reaction process.

5. The production method according to claim 1 , wherein the step of the dehydrofluorination reaction is performed in a gas phase.

6. The production method according to claim 1 , wherein the step of the dehydrofluorination reaction is performed by a gas-phase continuous flow process.

7. The production method according to claim 1 , wherein the step of the dehydrofluorination reaction is performed in the presence of a cyclic halogen carbide compound in which all hydrogen atoms bonded to carbon atoms in a hydrocarbon compound are replaced by halogen atoms,
wherein the cyclic halogen carbide compound is the compound represented by formula (4):

wherein A 3 , A 4 , A 5 , A 6 , A′, A 8 , A 9 , and A 10 are the same or different and each is a fluorine atom or a perfluoroalkyl group.

8. A method for producing a halogenated butyne compound represented by formula (3A):
CX 1 X 2 X 3 C≡CCX 5 X 6 X 7 (3A)

wherein X′, X 2 , X 3 , X 5 , X 6 , and X 7 are the same or different and each is a halogen atom,
the method comprising:
(IA) producing the composition containing the halogenated butene compound represented by formula (2A) by the production method according to claim 1 ;
(IIA) after step (IA), removing hydrogen fluoride; and
(IIIA) after step (IIA), subjecting the obtained composition
to a dehydrohalogenation reaction in a gas phase to produce the halogenated butyne compound represented by formula (3A):
CX 1 X 2 X 3 C≡CCX 5 X 6 X 7 (3A)

wherein X′, X 2 , X 3 , X 5 , X 6 , and X 7 are as defined above,
wherein the dehydrohalogenation reaction is performed in the presence of at least one catalyst selected from the group consisting of an activated carbon catalyst, a chromium oxide catalyst, and a silica alumina catalyst.

Assignees

• Daikin Ind Ltd

Inventors

• Etou Yuusuke
• Nakamura Shingo

Classifications

• C07C17/25 Primary

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

• C07C21/18

  containing fluorine · CPC title

• C07C17/087 Primary

  to unsaturated halogenated hydrocarbons · CPC title

• C07C21/22

  containing carbon-to-carbon triple bonds · CPC title

• H10P50/242

  of Group IV materials · CPC title