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CN-117222613-B - Process for producing fluoroalkyne compound

CN117222613BCN 117222613 BCN117222613 BCN 117222613BCN-117222613-B

Abstract

The present invention provides a process for producing a fluorinated alkyne compound represented by the general formula (1) wherein R 1 C≡CR 2 [R 1 and R 2 are the same or different and each represents a fluorine atom or a fluorinated alkyl group ], which comprises the step of dehydrofluorinating a fluorinated alkyne compound represented by the general formula (2) wherein R 1 CHX 1 CFX 2 R 2 [R 1 and R 2 are the same or different and wherein X 1 is a fluorine atom and X 2 is a hydrogen atom or X 1 is a hydrogen atom and X 2 is a fluorine atom in X 1 and X 2 , in the presence of an ether solvent, wherein at least 1 of the following (I) or (II) is satisfied, wherein the fluorinated alkyl group is a fluorinated alkyl group having 1 to 4 carbon atoms, and wherein the ether solvent is a chain ether compound, and wherein the dehydrofluorination reaction is performed in the presence of a base containing an alkali metal and/or an alkali earth metal hydroxide and/or alkoxide. By the production method, a fluoroalkyne compound can be efficiently synthesized from a fluoroalkane compound.

Inventors

  • ETOU YUUSUKE
  • NAKAMURA SHINGO

Assignees

  • 大金工业株式会社

Dates

Publication Date
20260512
Application Date
20220330
Priority Date
20210427

Claims (9)

  1. 1. A process for producing a fluoroalkyne compound represented by the general formula (1) below, characterized by comprising, Comprising a step of dehydrofluorinating a fluorinated alkane compound represented by the general formula (2) in the presence of an ether-containing solvent and a base containing an alkali metal and/or alkaline earth metal hydroxide, and satisfying at least 1 of the following items (I) or (II), R 1 C≡CR 2 (1) In the formula (1), R 1 and R 2 are the same or different and each represents a fluorine atom or a fluoroalkyl group, R 1 CHX 1 CFX 2 R 2 (2) In the formula (2), R 1 and R 2 are as above, and in X 1 and X 2 , X 1 is a fluorine atom and X 2 is a hydrogen atom, or X 1 is a hydrogen atom and X 2 is a fluorine atom; (I) The fluoroalkyl group is a fluoroalkyl group having 1 to 4 carbon atoms, (II) the ether is a chain ether.
  2. 2. The method of manufacturing according to claim 1, wherein, The total amount of the ether-containing solvent is set to 100 mass%, and the water concentration of the ether-containing solvent is 0.01-500 mass ppm.
  3. 3. The method of manufacturing according to claim 1 or 2, wherein, The number of ether bonds in the ether is 1-10.
  4. 4. The method of manufacturing according to claim 1 or 2, wherein, Satisfying said (I).
  5. 5. The method of manufacturing according to claim 4, wherein, The fluoroalkyl group is represented by the general formula (3), -CF 2 R 3 (3) In the formula (3), R 3 represents a fluorine atom or a fluoroalkyl group having 1 to 3 carbon atoms.
  6. 6. The method of manufacturing according to claim 1 or 2, wherein, Satisfying said (II).
  7. 7. The method of manufacturing as claimed in claim 6, wherein, The number of carbon atoms of the fluorinated alkyl group is 1 to 10.
  8. 8. The method of manufacturing as claimed in claim 6, wherein, The fluoroalkyl group is represented by the general formula (3), -CF 2 R 3 (3) In the formula (3), R 3 represents a fluorine atom or a fluoroalkyl group having 1 to 9 carbon atoms.
  9. 9. The method of manufacturing according to claim 1 or 2, wherein, The reaction temperature of the dehydrofluorination reaction is 0-300 ℃.

Description

Process for producing fluoroalkyne compound Technical Field The present invention relates to a method for producing a fluoroalkyne compound. Background Fluoroalkyne compounds are expected to be used for cleaning gases, etching gases, refrigerants, heat transfer media, blocks for organic synthesis, and the like. As a method for producing such a fluorinated alkyne compound, for example, non-patent document 1 discloses obtaining a fluorinated alkyne compound from a fluorinated alkane compound by a dehydrofluorination reaction using a base such as Lithium Diisopropylamide (LDA). Prior art literature Non-patent literature Non-patent document 1 tetrahedron,1988, vol.44, no.10, p.2865-2874 Disclosure of Invention Problems to be solved by the invention The purpose of the present invention is to provide a method for efficiently synthesizing a fluoroalkyne compound from a fluoroalkane compound. Means for solving the problems The invention includes the following aspects. A process for producing a fluoroalkyne compound represented by the general formula (1) which comprises a step of dehydrofluorinating a fluoroalkyne compound represented by the general formula (2) in the presence of an ether-containing solvent, wherein at least 1 of the following items (I) or (II) is satisfied. R1C≡CR2 (1) [ Wherein R 1 and R 2 are the same or different and each represents a fluorine atom or a fluoroalkyl group. ] R1CHX1CFX2R2 (2) [ Wherein R 1 and R 2 are the same as defined above, and X 1 and X 2 wherein X 1 is a fluorine atom and X 2 is a hydrogen atom, or wherein X 1 is a hydrogen atom and X 2 is a fluorine atom. ] (I) The fluoroalkyl group is a fluoroalkyl group having 1 to 4 carbon atoms. (II) the ether is a chain ether, and the dehydrofluorination reaction is carried out in the presence of a solvent containing the chain ether and a base containing an alkali metal and/or alkaline earth metal hydroxide and/or alkoxide. The production method according to item 1, wherein the total amount of the solvent is 100 mass%, and the water content of the solvent is 0.01 to 500 mass ppm. The method according to item 3, wherein the number of ether bonds in the ether is 1 to 10. The production method according to any one of items 1 to 3, wherein (I) is satisfied. The method according to item 5, wherein the fluoroalkyl group is represented by the general formula (3). -CF2R3 (3) [ Wherein R 3 represents a fluorine atom or a fluoroalkyl group having 1 to 3 carbon atoms. ] The production method according to item 4 or 5, wherein the dehydrofluorination reaction is performed in the presence of a base. The method according to item 7, wherein the alkali is an alkali metal hydroxide and/or an alkaline earth metal alkoxide. The production method according to any one of items 1 to 3, wherein (II) is satisfied. The method according to item 9, wherein the fluoroalkyl group has 1 to 10 carbon atoms. The production method according to item 8 or 9, wherein the fluoroalkyl group is represented by general formula (3). -CF2R3 (3) [ Wherein R 3 represents a fluorine atom or a fluoroalkyl group having 1 to 9 carbon atoms. ] The production method according to any one of items 1 to 10, wherein the dehydrofluorination reaction is carried out at a reaction temperature of 0 to 300 ℃. A composition comprising a fluoroalkyne compound represented by the general formula (1) and a fluoroalkene compound represented by the general formula (4), R1C≡CR2 (1) [ Wherein R 1 and R 2 are the same or different and each represents a fluorine atom or a fluoroalkyl group. ] R1CF＝CHR2 (4) [ Wherein R 1 and R 2 are as defined above. ] The total amount of the composition is set to 100 mol%, the content of the fluoroalkyne compound is 25.00 to 75.00 mol%, the content of the fluoroalkene compound is 25.00 to 75.00 mol%, and the total content of the fluoroalkyne compound and the fluoroalkene compound is 90.00 to 100.00 mol%. The composition of item 12 for use as a cleaning gas, etching gas, refrigerant, heat transfer medium or block for organic synthesis. The use of the composition of item 12 as a cleaning gas, etching gas, refrigerant, heat transfer medium, or block for organic synthesis. Effects of the invention According to the present invention, there is provided a method for synthesizing a fluoroalkyne compound from a fluoroalkane compound with high efficiency. Detailed Description In this specification, "containing" is a concept including any of "including", "consisting essentially of only" and "consisting of (consist of)". In the present specification, "a to B" means a or more and B or less when the numerical range is expressed. In the present invention, the term "selectivity" means a ratio (mol%) of the total molar amount of the target compounds contained in the effluent gas from the outlet of the reactor to the total molar amount of the compounds other than the raw material compounds in the effluent gas. In the present invention, the "conversion" means a ratio (mol%) of the total molar