Process for preparing 3,3,3-trifluoroprop-1-ene

Patent metadata

Field	Value
Publication number	US-11780794-B2
Application number	US-202318094544-A
Country	US
Kind code	B2
Filing date	Jan 9, 2023
Priority date	Mar 10, 2017
Publication date	Oct 10, 2023
Grant date	Oct 10, 2023

Abstract

The present application provides a process of preparing 3,3,3-trifluoroprop-1-ene, comprising reacting 3-chloro-1,1,1-trifluoropropane with a base in an aqueous solvent component in the absence of a phase transfer catalyst.

First claim

What is claimed is:

1. A process of preparing a mixture of 3,3,3-trifluoropropene (HFO-1243zf) and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), comprising reacting a mixture of 3-chloro-1,1,1-trifluoropropane (HCFC-253fb) and 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db) with a base in a liquid phase comprising an aqueous solvent with up to 40 weight percent of an organic solvent and in the absence of a phase transfer catalyst.

2. The process of claim 1 wherein the organic solvent is elected from one of methanol, ethanol, n-propanol, isopropanol, and butanol.

3. The process of claim 1 wherein the base is a metal hydroxide base, a metal carbonate base, a metal phosphate base, or a metal fluoride base.

4. The process of claim 1 wherein the base is NaOH, KOH, LiOH, CsOH, Ca(OH)2, Zn(OH)2, Na2CO3, K2CO3, K3PO4, Na3PO4, KF, or CsF.

5. The process of claim 1 , wherein the base is KOH or NaOH.

6. The process of claim 5 , wherein the base is NaOH.

7. The process of claim 1 , wherein about 0.01 to about 5 molar equivalents of base is used based on one molar equivalent of 3-chloro-1,1,1-trifluoropropane.

8. The process of claim 1 , wherein the reacting is conducted at a temperature of from about bout 40° C. to about 80° C.

9. The process of claim 1 , wherein the reacting is conducted at a temperature of from about bout 55° C. to about 65° C.

10. The process of claim 1 , wherein the reacting is conducted at a pressure selected from one of between 5 psig to about 150 psig, 0 psig to about 100 psig and −10 to about 100 psig.

11. A process of claim 1 , wherein the selectivity to and 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is at least 90 mole percent.

12. The process of claim 1 , wherein the 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is isolated.

13. The process of claim 12 , wherein about at least about 50 to at least about 99 weight percent of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) is isolated.

14. The process of claim 1 , wherein the reacting is conducted at a temperature of from about 35° C. to about 80° C. and at a pressure of about 5 psig to about 150 psig.

15. The process of claim 1 , wherein the reaction is conducted in the presence of hydrofluoric acid.

Assignees

• Chemours Co Fc Llc

Inventors

• Sun Xuehui
• Krause Karl Robert

Classifications

• C07C17/25 Primary

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• C07C21/18

  containing fluorine · CPC title

• B01J27/10

  Chlorides · CPC title

• C07C17/04

  to unsaturated halogenated hydrocarbons · CPC title

• C07C17/07

  by addition of hydrogen halides · CPC title