Process for the preparation of 1-chloro-3,3,3-trifluoropropene using a phase transfer catalyst
View Patent ↗Disclosed is a process in which the fluorination of an organic reactant comprising 1,1,1,3,3-pentachloropropane (240fa) with anhydrous HF is conducted in the presence of an effective amount of a phase-transfer catalyst which facilitates the reaction between these incompatible reaction components to produce 1-chloro-3,3,3-trifluoro-propene (1233zd). Other organic reactant materials include 1,1,3,3-tetrachloropropene (HCO-1230za), 1,3,3,3-tetrachloropropene (HCO-1230zd), and various mixtures with or without 240fa.
1. A process to produce 1-chloro-3,3,3-trifluoropropene (1233zd) comprising the fluorination of an organic reactant comprising 1,1,1,3,3-pentachloropropane (240fa) with anhydrous hydrogen fluoride (HF) in the presence of an effective amount of a phase-transfer catalyst.
2. The process of claim 1 , wherein the 240fa is in a mixture with 1,1,3,3-tetrachloropropene (HCO-1230za).
3. The process of claim 1 , wherein the 240fa is in a mixture with 1,3,3,3-tetrachloropropene (HCO-1230zd).
4. The process of claim 1 , wherein the 240fa is in a mixture with both 1,1,3,3-tetrachloropropene (HCO-1230za) and 1,3,3,3-tetrachloropropene (HCO-1230zd).
5. The process of claim 1 , wherein the phase-transfer catalyst comprises an onium salt.
6. The process of claim 5 , wherein the onium salt comprises a quaternary phosphonium salt.
7. The process of claim 6 , wherein quaternary phosphonium salt is selected from the group consisting of tetra-n-butyl-phosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium chloride, triphenylmethylphosphonium bromide, and triphenylmethylphosphonium chloride.
8. The process of claim 5 , wherein the onium salt comprises a quaternary ammonium salt.
9. The process of claim 8 , wherein the quaternary ammonium salt is selected from the group consisting of tetramethylammonium chloride, tetramethylammonium bromide, benzyltriethylammonium chloride, methyltrioctylammonium chloride, tetra-n-butylammonium chloride, tetra-n-butylammonium bromide, and tetra-n-butylammonium hydrogen sulfate.
10. The process of claim 1 , wherein the effective amount of the phase-transfer catalyst used relative to the amount of the organic reactant is from about 0.001 to about 10 mol %.
11. The process of claim 1 , wherein the effective amount of the phase-transfer catalyst used relative to the amount of the organic reactant is from about 0.01 to about 5 mol %.
12. The process of claim 1 , wherein the effective amount of the phase-transfer catalyst used relative to the amount of the organic reactant is from about 0.05 to about 5 mol %.
13. A process to produce 1-chloro-3,3,3-trifluoropropene (1233zd) comprising the fluorination of an organic reactant comprising 1,1,3,3-tetrachloropropene (HCO-1230za) with anhydrous hydrogen fluoride (HF) in the presence of an effective amount of a phase-transfer catalyst.
14. The process of claim 13 , wherein the 1230za is in a mixture with 1,1,1,3,3-pentachloropropane (240fa).
15. The process of claim 13 , wherein the 1230za is in a mixture with 1,3,3,3-tetrachloropropene (HCO-1230zd).
16. The process of claim 13 , wherein the 1230za is in a mixture with both 1,1,1,3,3-pentachloropropane (240fa) and 1,3,3,3-tetrachloropropene (HCO-1230zd).
17. A process to produce 1-chloro-3,3,3-trifluoropropene (1233zd) comprising the fluorination of an organic reactant comprising 1,3,3,3-tetrachloropropene (HCO-1230zd) with anhydrous hydrogen fluoride (HF) in the presence of an effective amount of a phase-transfer catalyst.
18. The process of claim 17 , wherein the 1230zd is in a mixture with 1,1,1,3,3-pentachloropropane (240fa).
19. The process of claim 17 , wherein the 1230zd is in a mixture with 1,1,3,3-tetrachloropropene (HCO-1230za).
20. The process of claim 17 , wherein the 1230zd is in a mixture with both 1,1,1,3,3-pentachloropropane (240fa) and 1,1,3,3-tetrachloropropene (HCO-1230za).
21. The process of claim 1 , wherein the fluorination reaction is conducted in the presence of a polar aprotic solvent.
22. The process of claim 21 , wherein polar aprotic solvent is selected from the group consisting of dimethylformamide, and dimethyl sulfoxide.
23. The process of claim 21 , wherein an effective amount of the polar aprotic is used, relative to the amount of organic reactant.
24. The process of claim 23 , wherein the amount of solvent used relative to the amount of organic reactant is from about 0.001 to about 10 mol %.
25. The process of claim 23 , wherein the amount of solvent used relative to the amount of organic reactant is from about 0.01 to about 5 mol %.
26. The process of claim 23 , wherein the amount of solvent used relative to the amount of organic reactant is from about 0.05 to about 5 mol %.
27. The process of claim 1 , wherein the phase-transfer catalyst is selected from the group consisting of 4-dialkylaminopyridinium salts, tetraphenylarsonium chloride, bis[tris(dimethyl-amino)phosphine]iminium chloride, and tetratris[tris(dimethylamino)phosphinimino]phosphonium chloride.