Method for producing hydrofluoroolefin

Patent metadata

Field	Value
Publication number	US-2017144949-A1
Application number	US-201715425283-A
Country	US
Kind code	A1
Filing date	Feb 6, 2017
Priority date	Aug 25, 2014
Publication date	May 25, 2017
Grant date	—

Abstract

A method for producing a hydrofluoroolefin, which comprises reacting a chlorofluoroolefin represented by the following formula (1) with hydrogen in the presence of a platinum group metal catalyst supported on a carbon carrier, to obtain a hydrofluoroolefin represented by the following formula (2),
wherein the carbon carrier has acidic functional groups, and the total acidic functional group amount in the carbon carrier is at most 50 μmol/g:

CZX═CClY   (1)

wherein X is F or Cl, Y is F, Cl or H, and Z is F or CF 3 ;
CZX′═CHY′  (2)

wherein X′ is F when X is F, or X′ is H when X is Cl, Y′ is F when Y is F, or Y′ is H when Y is Cl or H, and Z is the same as Z in the formula (1).

First claim

What is claimed is:

1 . A method for producing a hydrofluoroolefin, which comprises reacting a chlorofluoroolefin represented by the following formula (1) with hydrogen in the presence of a platinum group metal catalyst supported on a carbon carrier, to obtain a hydrofluoroolefin represented by the following formula (2),
wherein the total acidic functional group amount in the carbon carrier is at most 50 μmol/g:
CZX═CClY   (1)

wherein X is a fluorine atom or a chlorine atom, Y is a fluorine atom, a chlorine atom or a hydrogen atom, and Z is a fluorine atom or CF 3 ;
CZX′═CHY′  (2)

wherein X′ is a fluorine atom when X is a fluorine atom, or X′ is a hydrogen atom when X is a chlorine atom, Y′ is a fluorine atom when Y is a fluorine atom, or Y′ is a hydrogen atom when Y is a chlorine atom or a hydrogen atom, and Z is the same as Z in the formula (1).

2 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the platinum group metal catalyst is composed of palladium, a palladium alloy, rhodium or platinum.

3 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the platinum group metal catalyst is composed of an alloy of a platinum group element and gold.

4 . The method for producing a hydrofluoroolefin according to claim 3 , wherein the platinum group metal catalyst is composed of an alloy of palladium and gold.

5 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the total acidic functional group amount in the carbon carrier is at most 30 μmol/g.

6 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the total acidic functional group amount in the carbon carrier is at most 20 μmol/g.

7 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the carbon carrier has a specific surface area of from 10 to 2,000 m 2 /g.

8 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the amount of the platinum group metal catalyst supported is from 0.1 to 10 mass % based on the carbon carrier.

9 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the chlorofluoroolefin and hydrogen are introduced to a catalyst layer of a tubular reactor packed with the carbon carrier supporting the catalyst, and reacted in a gaseous phase.

10 . The method for producing a hydrofluoroolefin according to claim 9 , wherein the tubular reactor has a gas introduction part and a gas discharge part, and the chlorofluoroolefin and hydrogen are introduced to the gas introduction part and hydrogen is introduced from at least one point between the gas introduction part and the gas discharge part.

11 . The method for producing a hydrofluoroolefin according to claim 9 , wherein the reaction is carried out while the maximum temperature of the catalyst layer is controlled to be at most 130° C.

12 . The method for producing a hydrofluoroolefin according to claim 9 , wherein the proportion of hydrogen to the chlorofluoroolefin introduced to the catalyst layer is from 0.1 to 0.7 as represented by the ratio (H 2 /Cl) of the total number of moles of hydrogen to the number of moles of chlorine atoms in the chlorofluoroolefin.

13 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the chlorofluoroolefin and hydrogen are reacted in a liquid phase in the presence of the carbon carrier supporting the catalyst.

14 . The method for producing a hydrofluoroolefin according to claim 1 , wherein the chlorofluoroolefin is at least one member selected from the group consisting of chlorotrifluoroethylene, trans-1,2-dichloro-1,2-difluoroethylene, cis-1,2-dichloro-1,2-difluoroethylene, 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene.

15 . The method for producing a hydrofluoroolefin according to claim 1 , wherein 2,3,3,3-tetrafluoropropene is produced from 1,1-dichloro-2,3,3,3-tetrafluoropropene.

Assignees

• Asahi Glass Co Ltd

Inventors

• Wang Xu
• Terazono Shinji
• Kanda Masahiro
• Kawaguchi Satoshi
• Kasagawa Mitsugu

Classifications

• C07C17/354

  by hydrogenation · CPC title

• B01J23/72

  Copper · CPC title

• B01J23/48

  Silver or gold · CPC title

• B01J23/50

  Silver · CPC title

• B01J23/42

  Platinum · CPC title