Dehalogenation of trans-1-chloro-3,3,3-trifluoropropene
View Patent ↗The present invention is related to making hydrofluorocarbons (HCFCs), more specifically, 3,3,3-trifluoropropyne (TFP), from trans-1-chloro-3,3,3-trifluoropropene (trans-1233zd) by contacting the trans-1233zd with a base. Preferably, the base is potassium hydroxide or potassium tert-butoxide, which may or may not be dissolved in as solvent.
1. A method of making 3,3,3-trifluoropropyne from trans-1-chloro-3,3,3-trifluoropropene, the method comprising the steps of:
providing a first composition comprising potassium hydroxide;
contacting said first composition with a second composition comprising trans-1-chloro-3,3,3-trifluoropropene to make a third composition comprising 3,3,3-trifluoropropyne; and
wherein the first composition is heated to reflux temperature prior to contacting the first composition with the second composition.
2. The method of claim 1 , wherein the first composition further comprises calcium oxide.
3. The method of claim 1 , wherein the first composition further comprises tert-butanol.
4. The method of claim 1 , further comprising the step of obtaining a fourth composition comprising 3,3,3-trifluoropropyne from the third composition by maintaining the third composition at reflux temperature and collecting a fourth composition which has a higher concentration of 3,3,3-trifluoropropyne than said third composition.
5. The method of claim 1 , wherein the molar ratio of potassium hydroxide contacted with trans-1-chloro-3,3,3-trifluoropropene is at least 2.
6. The method of claim 1 , wherein the molar ratio of potassium hydroxide contacted with trans-1-chloro-3,3,3-trifluoropropene is between 3 and 5.
7. A method of making 3,3,3-trifluoropropyne from trans-1-chloro-3,3,3-trifluoropropene, the method comprising the steps of:
providing a first composition comprising potassium hydroxide;
contacting said first composition with a second composition comprising trans-1-chloro-3,3,3-trifluoropropene to make a third composition comprising 3,3,3-trifluoropropyne;
wherein the first composition optionally further comprises calcium oxide;
wherein the first composition optionally further comprises tert-butanol; and wherein the first composition is heated to reflux temperature prior to contacting the first composition with the second composition.
8. A method of making 3,3,3-trifluoropropyne from trans-1-chloro-3,3,3-trifluoropropene, the method comprising the steps of:
providing a first composition comprising potassium tert-butoxide dissolved in a solvent;
contacting said first composition with a second composition comprising trans-1-chloro-3,3,3-trifluoropropene to make a third composition comprising 3,3,3-trifluoropropyne; and
wherein the first composition is heated to reflux temperature prior to contacting the first composition with the second composition.
9. The method of claim 8 , wherein the first composition comprises tetrahydrofuran.
10. The method of claim 8 , wherein the first composition comprises tert-butanol.
11. The method of claim 8 , further comprising the step of obtaining a fourth composition comprising 3,3,3-trifluoropropyne from the third composition by maintaining the third composition at reflux temperature and collecting a fourth composition which has a higher concentration of 3,3,3-trifluoropropyne than said third composition.
12. The method of claim 8 , wherein the molar ratio of potassium tert-butoxide contacted with trans-1-chloro-3,3,3-trifluoropropene is at least 2.
13. The method of claim 8 , wherein the molar ratio of potassium tert-butoxide contacted with trans-1-chloro-3,3,3-trifluoropropene is between 3 and 5.
14. A method of making 3,3,3-trifluoropropyne from trans-1-chloro-3,3,3-trifluoropropene, the method comprising the steps of:
providing a first composition comprising potassium tert-butoxide dissolved in a solvent;
contacting said first composition with a second composition comprising trans-1-chloro-3,3,3-trifluoropropene to make a third composition comprising 3,3,3-trifluoropropyne;
wherein the first composition optionally comprises tetrahydrofuran; wherein the first composition optionally comprises tert-butanol; and
wherein the first composition is heated to reflux temperature prior to contacting the first composition with the second composition.