IP Library Granted Patent US 11,780,794
Granted Patent B2
US 11,780,794 · App. 18/094,544 · Granted Oct 10, 2023

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

Inventors: Xuehui Sun (Kennett Square, PA); Karl Robert Krause (Kennett Square, PA)
Assignee: THE CHEMOURS COMPANY FC, LLC
C07C17/25C07C21/18B01J27/10C07C17/04C07C17/07C07C19/10
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,780,794
App. No.
18/094,544
Granted
Oct 10, 2023
Kind
B2
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.

Claims (15)

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.

Assignments (1)
SECURITY INTEREST Recorded May 7, 2024
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 067341/0844 →