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EP-4737432-A1 - METHOD FOR PRODUCING FLUOROETHANE

EP4737432A1EP 4737432 A1EP4737432 A1EP 4737432A1EP-4737432-A1

Abstract

A method for producing a fluoroethane represented by the following formula (1): CH 2 X 1 CHX 2 X 3 (1) wherein X 1 , X 2 , and X 3 each independently represent a hydrogen atom or a fluorine atom, and at least one of X 1 , X 2 , and X 3 represents a fluorine atom, the method comprising step A of obtaining the fluoroethane from a chlorofluoroethane represented by the following formula (2) in the presence of a catalyst: CX 4 ClFCX 5 X 6 X 7 (2) wherein X 4 , X 5 , X 6 , and X 7 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom, and at least one of X 5 , X 6 , and X 7 represents a hydrogen atom.

Inventors

  • TAKAHASHI, KAZUHIRO
  • SHIMADA, TOMOO

Assignees

  • Daikin Industries, Ltd.

Dates

Publication Date
20260506
Application Date
20250730

Claims (10)

  1. A method for producing a fluoroethane represented by the following formula (1): CH 2 X 1 CHX 2 X 3 (1) wherein X 1 , X 2 , and X 3 each independently represent a hydrogen atom or a fluorine atom, and at least one of X 1 , X 2 , and X 3 represents a fluorine atom, the method comprising step A of obtaining the fluoroethane from a chlorofluoroethane represented by the following formula (2) in the presence of a catalyst: CX 4 ClFCX 5 X 6 X 7 (2) wherein X 4 , X 5 , X 6 , and X 7 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom, and at least one of X 5 , X 6 , and X 7 represents a hydrogen atom.
  2. The method according to claim 1, wherein the catalyst is at least one member selected from the group consisting of Ni, Pd, Pt, Rh, and Ru.
  3. The method according to claim 1 or 2, wherein the catalyst is supported on a carrier, and the carrier is a carbon-based carrier.
  4. The method according to claim 1 or 2, wherein the fluoroethane is 1,1,2-trifluoroethane (HFC-143), 1,1-difluoroethane (HFC-152a), 1,2-difluoroethane (HFC-152), or fluoroethane (HFC-161).
  5. The method according to claim 1 or 2, wherein the chlorofluoroethane is 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) or 1,1-dichloro-1,2,2-trifluoroethane (HCFC-123b).
  6. The method according to claim 1 or 2, wherein a hydrogenation reaction is performed in step A.
  7. The method according to claim 6, wherein the hydrogenation reaction is performed at a temperature of 150°C or higher and 350°C or lower.
  8. The method according to claim 6, wherein the hydrogenation reaction is performed by adding hydrogen to the chlorofluoroethane at an H 2 /chlorofluoroethane molar ratio of 1 or more and 20 or less.
  9. The method according to claim 6, wherein the hydrogenation reaction is performed in a gas phase.
  10. A method for producing a fluoroolefin, further comprising step B of subjecting a fluoroethane obtained by the production method of claim 1 or 2 to a dehydrofluorination reaction to obtain a fluoroolefin.

Description

Technical Field The present disclosure relates to a method for producing a fluoroethane. Background Art Fluoroethanes typified by 1,1,2-trifluoroethane (which hereinafter may be simply referred to as "HFC-143" in the present specification) are known as a starting material for producing various refrigerants. Various methods have been proposed for the production of fluoroethanes such as HFC-143. For example, Patent Literature 1 (PTL 1) proposes a technique for producing chlorotrifluoroethylene or trifluoroethylene by a hydrogenation reaction of 1,1,2-trichloro-1,2,2-trifluoroethylene (which hereinafter may be simply referred to as "CFC-113" in the present specification) or the like, in the presence of a hydrogenation catalyst. However, when a fluoroethane, such as HFC-143, is produced by the method disclosed in PTL 1, there is a problem in that the selectivity of the desired product is low. Furthermore, there is no disclosure of a method for obtaining a hydrofluoroethane from a hydrochlorofluorocarbon (which hereinafter may be simply referred to as "HCFC" in the present specification). Citation List Patent Literature PTL 1: JPH4-117333A Summary of Invention Technical Problem In view of the circumstances described above, an object of the present disclosure is to provide a method for obtaining a hydrofluoroethane with high selectivity using a hydrochlorofluoroethane as a starting material. Solution to Problem The present inventors conducted extensive research to achieve the above object, and found that a fluoroethane can be obtained in a high yield by using a catalyst. Based on this finding, the inventors continued further research and have accomplished the present disclosure. Specifically, the present disclosure provides the following methods for producing a fluoroethane. Item 1. A method for producing a fluoroethane represented by the following formula (1):         CH2X1CHX2X3     (1) wherein X1, X2, and X3 each independently represent a hydrogen atom or a fluorine atom, and at least one of X1, X2, and X3 represents a fluorine atom, the method comprising step A of obtaining the fluoroethane from a chlorofluoroethane represented by the following formula (2) in the presence of a catalyst:         CX4ClFCX5X6X7     (2) wherein X4, X5, X6, and X7 each independently represent a hydrogen atom, a fluorine atom, or a chlorine atom, and at least one of X5, X6, and X7 represents a hydrogen atom. Item 2. The method according to Item 1, wherein the catalyst is at least one member selected from the group consisting of Ni, Pd, Pt, Rh, and Ru. Item 3. The method according to Item 1 or 2, wherein the catalyst is supported on a carrier, and the carrier is a carbon-based carrier. Item 4. The method according to any one of Items 1 to 3, wherein the fluoroethane is 1,1,2-trifluoroethane (HFC-143), 1,1-difluoroethane (HFC-152a), 1,2-difluoroethane (HFC-152), or fluoroethane (HFC-161). Item 5. The method according to any one of Items 1 to 4, wherein the chlorofluoroethane is 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) or 1,1-dichloro-1,2,2-trifluoroethane (HCFC-123b). Item 6. The method according to any one of Items 1 to 5, wherein a hydrogenation reaction is performed in step A. Item 7. The method according to Item 6, wherein the hydrogenation reaction is performed at a temperature of 150°C or higher and 350°C or lower. Item 8. The method according to Item 6 or 7, wherein the hydrogenation reaction is performed by adding hydrogen to the chlorofluoroethane at an H2/chlorofluoroethane molar ratio of 1 or more and 20 or less. Item 9. The method according to any one of Items 6 to 8, wherein the hydrogenation reaction is performed in a gas phase. Item 10. A method for producing a fluoroolefin, further comprising step B of subjecting a fluoroethane obtained by the production method of any one of Items 1 to 9 to a dehydrofluorination reaction to obtain a fluoroolefin. Advantageous Effects of Invention The method for producing a fluoroethane according to the present disclosure described above enables a fluoroethane to be obtained in a high yield. Description of Embodiments In the present specification, the terms "comprise," "contain," and "include" encompass the concepts of comprising, consisting essentially of, and consisting of. 1. Method for Producing Fluoroethane The method for producing a fluoroethane of the present disclosure is a method for producing a fluoroethane represented by the following formula (1)         CH2X1CHX2X3     (1) wherein X1, X2, and X3 each independently represent a hydrogen atom or a fluorine atom, and at least one of X1, X2, and X3 represents a fluorine atom. The method for producing a fluoroethane of the present disclosure comprises step A of obtaining the fluoroethane from a chlorofluoroethane represented by the following formula (2) in the presence of a catalyst:         CX4ClFCX5X6X7     (2) wherein X4, X5, X6, and X7 each independently represent a hydrogen atom, a fluorine atom, or a chlorine