Method of manufacturing 1-chloro-2,3,3-trifluoropropene
There is provided a method of efficiently manufacturing 1-chloro-2,3,3-trifluoropropene by an industrially feasible method by using a raw material which is easy to obtain. A method of manufacturing 1-chloro-2,3,3-trifluoropropene, including subjecting 3-chloro-1,1,2,2-tetrafluoropropane to a dehydrofluorination reaction in the presence of a base.
1. A method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene, comprising:
subjecting 3-chloro-1,1,2,2-tetrafluoropropane to a dehydrofluorination reaction in the presence of a base, under a reaction temperature of 10 to 80° C., to produce (Z)-1-chloro-2,3,3-trifluoropropene.
2. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein the base is at least one selected from the group consisting of a metal hydroxide, a metal oxide, and a metal carbonate.
3. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein the base is a metal hydroxide.
4. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein the base is at least one selected from the group consisting of potassium hydroxide and sodium hydroxide.
5. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein an amount of the base is 0.5 to 10.0 mol with respect to 1 mol of the 3-chloro-1,1,2,2-tetrafluoropropane.
6. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein the 3-chloro-1,1,2,2-tetrafluoropropane is subjected to a dehydrofluorination reaction in a liquid phase in the presence of a solvent and the base.
7. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 6 , wherein the solvent is water.
8. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 6 , wherein an amount of the base is 0.5 mass% to 48 mass% with respect to total mass of the solvent and the base.
9. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 6 , wherein the dehydrofluorination reaction is performed in the presence of a phase-transfer catalyst.
10. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 9 , wherein the phase-transfer catalyst is a quaternary ammonium salt.
11. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 10 , wherein the quaternary ammonium salt is at least one selected from the group consisting of tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, and methyltri-n-octylammonium chloride.
12. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 6 , wherein the dehydrofluorination reaction is performed in the presence of a water-soluble organic solvent capable of dissolving the 3-chloro-1,1,2,2-tetrafluoropropane.
13. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 12 , wherein the water-soluble organic solvent is used in a proportion of 1 to 200 parts by mass to 100 parts by mass of the 3-chloro-1,1,2,2-tetrafluoropropane.
14. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein the base is at least one selected from the group consisting of potassium hydroxide and sodium hydroxide, the dehydrofluorination reaction is performed in the presence of a phase-transfer catalyst which is at least one selected from the group consisting of tetra-n-butylammonium chloride, tetra-n-butylammonium bromide and methyltri-n-octylammonium chloride, and an amount of the base is 1.05 to 2.99 mol with respect to 1 mol of the 3-chloro-1,1,2,2-tetrafluoropropane.
15. The method of manufacturing (Z)-1-chloro-2,3,3-trifluoropropene according to claim 1 , wherein a yield of (Z)-1-chloro-2,3,3-trifluoropropene is at least 86.2%.