Processes for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene
View Patent ↗To provide a simple and economical process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, which does not require purification of the raw material component obtained in the form of a mixture of isomers, and a process for producing 2,3,3,3-tetrafluoropropene from the product thereby obtained. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, characterized by bringing a mixture of dichloropentafluoropropane isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane into contact with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture, and a process for producing 2,3,3,3-tetrafluoropropene from the 1,1-dichloro-2,3,3,3-tetrafluoropropene thereby obtained.
1. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, comprising contacting a mixture of dichloropentafluoropropane isomers which comprises 1,1-dichloro-2,2,3,3,3-pentafluoropropane with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture.
2. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the mixture of dichloropentafluoropropane isomers comprises, in addition to the 1,1-dichloro-2,2,3,3,3-pentafluoropropane, at least one isomer selected from 1,3-dichloro-1,2,2,3,3-pentafluoropropane, 2,2-dichloro-1,1,3,3,3-pentafluoropropane, 1,2-dichloro-1,2,3,3,3-pentafluoropropane and 2,3-dichloro-1,1,2,3,3-pentafluoropropane.
3. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the content of the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture of dichloropentafluoropropane isomers is at most 99.5 mol %.
4. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the concentration of the aqueous alkali solution is from 0.5 mass % to 40 mass %.
5. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the temperature at which the mixture of dichloropentafluoropropane isomers is brought into contact with the aqueous alkali solution in the presence of a phase transfer catalyst is from 0 to 80° C.
6. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the temperature at which the mixture of dichloropentafluoropropane isomers is brought into contact with the aqueous alkali solution in the presence of a phase transfer catalyst is from 0 to 25° C.
7. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting the 1,1-dichloro-2,3,3,3-tetrafluoropropene obtained by the process as defined in claim 1 , with hydrogen in the presence of a catalyst.
8. The process for producing 2,3,3,3-tetrafluoropropene according to claim 7 , wherein the amount of the hydrogen which is used for the reaction for forming the 2,3,3,3-tetrafluoropropene, is less than 3 mol to 1 mol of the 1,1-dichloro-2,3,3,3-tetrafluoropropene.
9. The process for producing 2,3,3,3-tetrafluoropropene according to claim 7 , wherein the reaction for forming the 2,3,3,3-tetrafluoropropene is carried out in the presence of an inert gas.
10. The process for producing 2,3,3,3-tetrafluoropropene according to claim 9 , wherein the reaction for forming the 2,3,3,3-tetrafluoropropene is carried out in the presence of an inert gas in an amount of at least 0.5 time by mol to the 1,1-dichloro-2,3,3,3-tetrafluoropropene.
11. The method of claim 1 , wherein said aqueous alkali solution comprises at least one alkali selected from the group consisting of sodium hydroxide and potassium hydroxide.
12. The method of claim 1 , wherein an amount of said aqueous alkali solution is 0.5 to 1.5 mol equivalents to an amount of 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
13. The method of claim 1 , wherein said phase transfer catalyst is at least one catalyst selected from the group consisting of a quaternary ammonium salt, a quaternary phosphonium salt substituted by a hydrocarbon group and a crown ether.
14. The method of claim 1 , wherein said phase transfer catalyst is in an amount of 0.001 to 5 mass % to a mass of said 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
15. The method of claim 1 , wherein said phase transfer catalyst is in an amount of 0.01 to 1 mass % to a mass of said 1,1-dichloro-2,2,3,3,3-pentafluoropropane.
16. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the content of the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture of dichloropentafluoropropane isomers is at least 10 mol %.
17. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein the content of the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture of dichloropentafluoropropane isomers is at least 48 mol %.
18. The process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene according to claim 1 , wherein said mixture of dichloropentafluoropropane isomers is brought into contact with the aqueous alkali solution in the presence of a phase transfer catalyst at at pressure of 98,000-200,000 Pa and a temperature of 50-80° C.