Synthesis of 3,3,3-trifluoropropyne
View Patent ↗In accordance with the present invention, processes of synthesizing 3,3,3-trifluoropropyne from 1,3,3,3-tetrafluoropropene, 1-chloro-3,3,3-trifluoropropene, and/or 1,1,1,3,3-pentafluoropropane are provided.
1. A process of synthesizing 3,3,3-trifluoropropyne, the process comprising the steps of:
providing a solution of 1-chloro-3,3,3-trifluoropropene in tetrahydrofuran; and,
adding potassium tert-butoxide to the solution to yield the 3,3,3-trifluoropropyne.
2. The process of claim 1 , wherein the solution of 1-chloro-3,3,3-trifluoropropene is at about 50-60° C. during the addition of potassium tert-butoxide to the solution.
3. The process of claim 1 , wherein the 1-chloro-3,3,3-trifluoropropene is cis-1-chloro-3,3,3-trifluoropropene.
4. The process of claim 2 , wherein the 1-chloro-3,3,3-trifluoropropene is cis-1-chloro-3,3,3-trifluoropropene.
5. A process of synthesizing 3,3,3-trifluoropropyne, the process comprising the steps of:
providing a compound selected from the group consisting of 1,3,3,3-tetrafluoropropene, 1-chloro-3,3,3-trifluoropropene, and 1,1,1,3,3-pentafluoropropane;
mixing the compound with a solvent to make a first mixture;
adding sodium amide to the first mixture to make a second mixture;
adding hydrochloric acid to the second mixture to yield the 3,3,3-trifluoropropyne.
6. The process of claim 5 , wherein the compound is selected from the group consisting of 1,3,3,3-tetrafluoropropene and 1-chloro-3,3,3-trifluoropropene.
7. The process of claim 6 , wherein the majority of the compound is in a cis form.
8. The process of claim 6 , wherein the majority of the compound is in a trans form.
9. The process of claim 6 , wherein the molar ratio of sodium amide to the compound in the first mixture is 2 or greater.
10. The process of claim 9 , wherein the molar ratio of sodium amide to the compound in the first mixture is between 2 and 3.
11. A process of synthesizing 3,3,3-trifluoropropyne, the process comprising the steps of:
providing a solution comprising potassium hydroxide; and,
heating a first mixture comprising trans-1-chloro-3,3,3-trifluoropropene, the solution, and a catalyst to yield the 3,3,3-trifluoropropyne.
12. The process of claim 11 , wherein the first mixture is heated to at least 50° C. for at least 20 hours.
13. The process of claim 11 , wherein the solution comprising potassium hydroxide comprises at least 20% potassium hydroxide.
14. The process of claim 11 , wherein the solution comprising potassium hydroxide comprises the catalyst.
15. The process of claim 14 , wherein the catalyst is aliquat 336.