Catalysts and methods for conversion of 1,1,2-trichloro-1,2,2-trifluoroethane (cfc-113) to 1,1,2-trifluoroethane (hfc-143)

Patent metadata

Field	Value
Publication number	US-2025066276-A1
Application number	US-202418807095-A
Country	US
Kind code	A1
Filing date	Aug 16, 2024
Priority date	Aug 22, 2023
Publication date	Feb 27, 2025
Grant date	—

Abstract

HFO-1132 and, in particular, HFO-1132E, may be produced from 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113). In a first step, 1,1,2-trifluoroethane (HFC-143) is produced by hydrogenating 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) by reaction with hydrogen in the presence of a catalyst to produce 1, 1,2-trifluoroethane (HFC-143). The highly exothermic hydrogenation step may be moderated by diluting the catalyst and/or by diluting the 1, 1,2-trichloro-1,2,2-trifluoroethane (CFC-113) feedstock. The 1, 1,2-trifluoroethane (HFC-143) may then be dehydrofluorinated in the presence of a catalyst to produce trans-1,2-difluoroethylene (HFO-1132E) and/or cis-1,2-difluoroethylene (HFO-1132Z). The cis-1,2-difluoroethylene (HFO-1132Z) may then be isomerized to produce trans-1,2-difluoroethylene (HFO-1132E).

First claim

What is claimed is:

1 . A method for producing 1,1,2-trifluoroethane (HFC-143), comprising:
hydrogenating 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) by reaction with hydrogen in the presence of a catalyst to produce 1,1,2-trifluoroethane (HFC-143), the catalyst comprising:
a catalytic material comprising from 0.1 to 1.0 wt. % of a catalytic metal supported on a support, based on a total weight of the catalytic metal and the support; and
a diluent material, wherein the amount of catalytic material is from 5 to 70 volume percent, based on the total volume of the catalytic material and diluent material.

2 . The method of claim 1 , wherein the amount of catalytic material is from 10 to 50 volume percent, based on the total volume of the catalytic material and the diluent material.

3 . The method of claim 1 , wherein the metal comprises palladium.

4 . The method of claim 1 , wherein the diluent comprises a metal or a metal alloy.

5 . The method of claim 1 , wherein the support is selected from alpha alumina, delta alumina, and theta alumina.

6 . The method of claim 1 , wherein the hydrogenation step is carried out at a temperature from about 100° C. to about 300° C.

7 . The method of claim 1 , wherein the hydrogenation step is carried out at a mole ratio of hydrogen to 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) of from 3:1 to 15:1.

8 . The method of claim 1 , wherein the hydrogenation step achieves a selectivity to 1,1,2-trifluoroethane (HFC-143) of greater than about 20%.

9 . The method of claim 1 , wherein the hydrogenation step achieves a combined selectivity to 1,1,2-trifluoroethane (HFC-143), 1-chloro-1,1,2-trifluoroethane (HCFC-133b), and 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) of greater than about 80%.

10 . The method of claim 1 , wherein the hydrogenation step achieves a combined selectivity to 1,1-difluoroethane (HFC-152a), ethane (HC-170), 1,1,1-trifluoroethane (HFC-143a) 1-chloro-1,2-difluoroethane (HCFC-142a), and chloroethane (HCC-160) of less than about 20%.

11 . The method of claim 1 , wherein the hydrogenation step is carried out at a contact time of from about 1 second to about 60 seconds.

12 . The method of claim 1 , further comprising the additional step of:
dehydrofluorinating 1,1,2-trifluoroethane (HFC-143) in the presence of a catalyst to produce trans-1,2-difluoroethylene (HFO-1132E) and/or cis-1,2-difluoroethylene (HFO-1132Z).

13 . A composition produced from the method of claim 1 , comprising:
trans-1,2-difluoroethylene (HFO-1132E) present in an amount of at least 95 wt. %; and 1, 1,1,-tritfluoroethane (HFC-143a) present in an amount of less than 5 wt. %, based on a total weight of the composition.

14 . A palladium metal catalyst useful for hydrogenating 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) by reaction with hydrogen to produce 1,1,2-trifluoroethane (HFC-143), the catalyst comprising:
a catalytic material comprising from 0.1 to 1.0 wt. % of palladium metal supported on an alumina (Al 2 O 3 ) support, based on a total weight of the catalytic metal and the support; and a diluent material, wherein the amount of catalytic material is from 5 to 70 volume percent, based on the total volume of the catalytic material and diluent material.

15 . The catalyst of claim 14 , wherein the amount of catalytic material is from 10 to 50 volume percent, based on the total volume of the catalytic material and the diluent material.

16 . The catalyst of claim 14 , wherein the support is selected from alpha alumina, delta alumina, and theta alumina.

17 . The catalyst of claim 14 , wherein the diluent comprises a metal or a metal alloy.

18 . A method for producing 1,1,2-trifluoroethane (HFC-143), comprising:
combining 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) with a feedstock diluent to form a reaction mixture; and reacting the 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) in the reaction mixture with hydrogen in the presence of a catalyst to produce a product mixture.

19 . The method of claim 18 , wherein the product mixture comprises 1,1,2-trifluoroethane (HFC-143), and the method further comprises the additional steps of:
separating the 1,1,2-trifluoroethane (HFC-143) from the product mixture; and conveying the 1,1,2-trifluoroethane (HFC-143) to the reactant mixture.

20 . The method of claim 19 , wherein the dilution composition comprises a mole ratio of 1,1,2-trifluoroethane (HFC-143) to 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113), from about 0.25:1 to about 10:1.

Assignees

• Honeywell Int Inc

Inventors

• Mahdavi-Shakib Akbar
• Wang Haiyou

Classifications

• C07C17/23 Primary

  by dehalogenation · CPC title

• C07C17/354

  by hydrogenation · CPC title

• C07C2523/44

  Palladium · CPC title

• C07C2523/56

  Platinum group metals · CPC title

• C07C17/25 Primary

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