Process for producing 1, 1-dichloro-2, 2, 3, 3, 3-pentafluoropropane
View Patent ↗To provide a process for producing, at a high content ratio, 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO1214ya). The process for producing HCFC-225ca of the present invention comprises subjecting a raw material composed of dichloropentafluoropropane (HCFC-225) including 2,2-dichloro-1,1,1,3,3-pentafluoropropane (HCFC225aa) to an isomerization reaction at a temperature of at most 290° C. in a gas phase in the presence of a metal oxide catalyst thereby to isomerize HCFC-225aa to HCFC-225ca.
1. A process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane, which comprises reacting a raw material comprising 2,2-dichloro-1,1,1,3,3-pentafluoropropane at a temperature of 150° C. to 290° C. in a gas phase in the presence of a metal oxide catalyst thereby to isomerize at least a part of 2,2-dichloro-1,1,1,3,3-pentafluoropropane in the raw material to 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
2. The process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane according to claim 1 , wherein the raw material further contains 1,3-dichloro-1,2,2,3,3-pentafluoropropane, and in the above reaction, at the same as isomerization of 2,2-dichloro-1,1,1,3,3-pentafluoropropane to 1,1-dichloro-2,2,3,3,3-pentafluoroporpane, at least a part of the 1,3-dichloro-1,2,2,3,3-pentafluoropropane is isomerized to 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
3. The process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane according to claim 1 or 2 , wherein the temperature for the reaction is at least 150° C. to 180° C.
4. The process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane according to claim 1 or 2 , wherein the metal oxide catalyst is an aluminum oxide type catalyst.
5. The process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane according to claim 1 or 2 , wherein the above metal oxide catalyst is a partially fluorinated metal oxide catalyst.
6. The process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane according to claim 1 or claim 2 , wherein the metal oxide catalyst is a partially fluorinated aluminum oxide catalyst.
7. The process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane according to claim 1 or claim 2 , wherein hydrochlorofluorocarbon compounds other than dichloropentafluoropropane, which are produced as by-products are less than 10 mol % based on the total amount of dichloropentafluoropropane in the reaction product.
8. A process for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane, which comprises:
subjecting dichloropentafluoropropane containing 1,1-dichloro-2,2,3,3,3-pentafluoropropane and 2,2-dichloro-1,1,1,3,3-pentafluoropropane to a dehydrofluorination reaction in an alkali aqueous solution in the presence of a phase-transfer catalyst to produce 1,1-dichloro-2,3,3,3-tetrafluoropropene from 1,1-dichloro-2,2,3,3,3-pentafluoropropane;
then, separating 1,1-dichloro-2,3,3,3-tetrafluoropropene from the reaction product; and
reacting dichloropentafluoropropane containing 2,2-dichloro-1,1,1,3,3-pentafluoropropane after separating 1,1-dichloro-2,3,3,3-tetrafluoropropene, at a temperature of 150° C. to 290° C. in a gas phase in the presence of a metal oxide catalyst thereby to isomerize at least a part of 2,2-dichloro-1,1,1,3,3-pentafluoropropane in the above dichloropentafluoropropane to 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
9. A process for producing 1,1-dichloro-2,2,3,3,3-tetrafluoropropene, which comprises:
subjecting dichloropentafluoropropane containing 1,1-dichloro-2,2,3,3,3-pentafluoropropane and 2,2-dichloro-1,1,1,3,3-pentafluoropropane to a dehydrofluorination reaction in an alkali aqueous solution in the presence of a phase-transfer catalyst to produce 1,1-dichloro-2,3,3,3-tetrafluoropropene from 1,1-dichloro-2,2,3,3,3-pentafluoropropane;
separating 1,1-dichloro-2,3,3,3-tetrafluoropropene from the above dehhydrofluorination reaction product;
reacting dichloropentafluoropropane containing 2,2-dichloro-1,1,1,3,3-pentafluoropropane after separating 1,1-dichloro-2,3,3,3-tetrafluoropropene, at a temperature of 150° C. to 290° C. in a gas phase in the presence of a metal oxide catalyst, to isomerize a part of 2,2-dichloro-1,1,1,3,3-pentafluoropropane in the above dichloropentafluoropropane thereby to produce dichloropentafluoropropane including 1,1-dichloro-2,2,3,3,3-pentafluoropropane and 2,2-dichloro-1,1,1,3,3-pentafluoropropane; and
repeating the above process to produce 1,1-dichloro-2,3,3,3-tetrafluoropropene from the obtained dichloropentafluoropropane.
10. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 9 , wherein the above isomerization reaction is carried out by adding 1,3-dichloro-1,2,2,3,3-pentafluoropropane to the dichloropentafluoropropane as the raw material for the isomerization reaction, so that at the same time as the isomerization of 2,2-dichloro-1,1,1,3,3-pentafluoropropane to 1,1-dichloro-2,2,3,3,3-pentatluoropropane, the 1,3-dichloro-1,2,2,3,3-pentafluoropropane is isomerized to 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
11. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 9 or 10 , wherein the isomerization reaction is carried out by adding 2,2-dichloro-1,1,1,3,3-pentafluoropropane to the dichloropentafluoropropane as the raw material for the isomerization reaction.