METHOD FOR PRODUCING trans-1,2-DIFLUOROETHYLENE (HFO-1132E)
Production of HFO-1132 and, in particular, HFO-1132E, is produced from chlorotrifluoroethylene (CTFE) and/or trifluoroethylene (HFO-1123). In a first step, 1,1,2-trifluoroethane (HFC-143) is produced by hydrogenating chlorotrifluoroethylene (CTFE) and/or trifluoroethylene (HFO-1123) by reaction with hydrogen in the presence of a catalyst at a temperature of between about 75° C. and about 225° C. The 1,1,2-trifluoroethane (HFC-143) may then be dehydrohalogenated in the presence of a catalyst to produce trans-1,2-difluoroethylene (HFO-1132E) and 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).
1 . A method for producing 1,1,2-trifluoroethane (HFC-143), comprising:
reacting a reactant composition comprising chlorotrifluoroethylene (CTFE) with hydrogen in the presence of a catalyst at a temperature of between about 75° C. and about 225° C. to produce a product mixture comprising 1,1,2-trifluoroethane (HFC-143).
2 . The method of claim 1 , wherein the temperature is between about 100° C. and about 200° C.
3 . The method of claim 1 , wherein the temperature is between about 120° C. and about 180° C.
4 . The method of claim 1 , wherein the reactant composition further comprises trifluoroethylene (HFO-1123).
5 . The method of claim 4 , wherein the reactant composition comprises:
from about 50 mol. % to about 99.99 mol. % of chlorotrifluoroethylene (CTFE); and
from about 0.01 mol. % to about 50 mol. % of trifluoroethylene (HFO-1123), based on total moles of chlorotrifluoroethylene (CTFE) and trifluoroethylene (HFO-1123).
6 . The method of claim 1 , wherein the catalyst is palladium.
7 . The method of claim 1 , wherein the catalyst is supported on a support selected from the group consisting of carbon and alumina.
8 . The method of claim 1 , wherein the catalyst is palladium supported on an alpha alumina support.
9 . The method of claim 1 , wherein the catalyst is palladium supported on a theta alumina support.
10 . The method of claim 1 , wherein the catalyst is palladium supported on a delta alumina support.
11 . The method of claim 1 , wherein the product mixture comprises:
about 50 mol. % to about 99.99 mol. % of 1,1,2-trifluoroethane (HFC-143); and
about 0.01 mol. % to about 50 mol. % of at least one of 1-chloro-1,1,2-trifluoroethane (HCFC-133b), 1-chloro-1,2,2-trifluoroethane (HCFC-133), and trifluoroethylene (HFO-1123), based on total moles of HFC-143, HCFC-133b, HCFC-133, and HFO-1123 in the product mixture.
12 . The method of claim 11 , wherein the product mixture further comprises at least one of:
0.01 mol. % to 5 mol. % of ethane (HC-170),
0.01 mol. % to 5 mol. % of 1,1,1-trifluoroethane (HFC-143a),
0.01 mol. % to 15 mol. % of 1,1,1,2-tetrafluoroethane (HFC-134a),
0.01 mol. % to 4 mol. % of 1,1-difluoroethane (HFC-152a),
0.01 mol. % to 6 mol. % of one or more HCFC-142 isomers, and
0.01 mol. % to 2 mol. % of chloroethane (HCC-160), based on total moles of organic components in the product mixture.
13 . The method of claim 12 , wherein the one or more HCFC-142 isomers comprises 1-chloro-1,2-difluoroethane (HCFC-142a), 1-chloro-2,2-difluoroethane (HCFC-142), or 1-chloro-1,1-difluoroethane (HCFC-142b).
14 . The method of claim 1 , wherein the reacting step achieves a combined selectivity to 1,1,2-trifluoroethane (HFC-143), 1-chloro-1,1,2-trifluoroethane (HCFC-133b), 1-chloro-1,2,2-trifluoroethane (HCFC-133), and trifluoroethylene (HFO-1123) of greater than 70% and less than or equal to 100%.
15 . The method of claim 1 , wherein the reacting step achieves a conversion of the reactant composition to 1,1,2-trifluoroethane (HFC-143) of greater than 80% and less than or equal to 100%.
16 . The method of claim 1 , wherein the reacting step achieves a selectivity to ethane (HC-170), chloroethane (HCC-160), HCFC-142 isomers, and 1,1,1-trifluoroethane (HFC-143a) of less than 10% and greater than or equal to 0%.
17 . The method of claim 1 , further comprising:
dehydrohalogenating 1,1,2-trifluoroethane (HFC-143) in the presence of a catalyst to produce a composition comprising trans-1,2-difluoroethylene (HFO-1132E) and cis-1,2-difluoroethylene (HFO-1132Z).
18 . The method of claim 17 , further comprising:
isomerizing cis-1,2-difluoroethylene (HFO-1132Z) to produce trans-1,2-difluoroethylene (HFO-1132E).
19 . A composition comprising:
from 90 mol. % to 95 mol. % of 1,1,2-trifluoroethane (HFC-143); and
from 5 mol. % to 10 mol. % of at least one of 1-chloro-1,1,2-trifluoroethane (HCFC-133b), 1-chloro-1,2,2-trifluoroethane (HCFC-133), and trifluoroethylene (HFO-1123), based on total moles of HFC-143, HCFC-133b, HCFC-133, and HFO-1123 in the composition.
20 . The composition of claim 19 , further comprising at least one of:
0.01 mol. % to 1 mol. % of ethane (HC-170),
0.01 mol. % to 1.6 mol. % of 1,1,1-trifluoroethane (HFC-143a),
0.01 mol. % to 0.5 mol. % of 1,1,1,2-tetrafluoroethane (HFC-134a),
0.01 mol. % to 1.7 mol. % of 1,1-difluoroethane (HFC-152a),
0.01 mol. % to 0.15 mol. % of one or more HCFC-142 isomers, and
0.01 mol. % to 0.5 mol. % of chloroethane (HCC-160), based on total moles of organic components in the composition.