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

Patent metadata

Field	Value
Publication number	US-10577296-B2
Application number	US-201815917376-A
Country	US
Kind code	B2
Filing date	Mar 9, 2018
Priority date	Mar 10, 2017
Publication date	Mar 3, 2020
Grant date	Mar 3, 2020

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 3,3,3-trifluoroprop-1-ene, comprising reacting 3-chloro-1,1,1-trifluoropropane with a base in an aqueous solvent component, wherein the reacting is conducted in the absence of a phase transfer catalyst, wherein the aqueous solvent component does not comprise an organic solvent.

2. The process of claim 1 , wherein the base is an aqueous base.

3. The process of claim 2 , 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 2 , wherein the base is NaOH, KOH, LiOH, CsOH, Ca(OH) 2 , Zn(OH) 2 , Na 2 CO 3 , K 2 CO 3 , K 3 PO 4 , Na 3 PO 4 , KF, or CsF.

5. The process of claim 2 , wherein the base is KOH or NaOH.

6. 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.

7. The process of claim 1 , wherein the reacting is conducted at a temperature of from about 20 ° C. to about 100 ° C.

8. The process of claim 1 , wherein the reacting is conducted at a pressure of about −10 psig to about 500 psig.

9. The process of claim 1 , wherein the reacting comprises mixing the 3-chloro-1,1,1-trifluoropropane and base with a mixing power of from about 0.1 to about 50 horsepower per 1000 gallons of the reaction mixture.

10. 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 230 psig.

11. The process of claim 1 , wherein the 3-chloro-1,1,1-trifluoropropane is prepared by a process comprising reacting 1,1,1,3-tetrachloropropane with hydrofluoric acid.

12. The process of claim 1 , further comprising chlorinating 3,3,3-trifluoropropene to form 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db).

13. The process of claim 12 , wherein said chlorinating comprises reacting with chlorine or HCl/oxygen.

14. The process of claim 12 , comprising dehydrochlorinating 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db) to form 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf).

15. The process of claim 14 , comprising reacting the 1,1,1-trifluoro-2,3-dichloropropane (HCFC-243db) with caustic to form 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf).

16. The process of claim 14 , further comprising hydrofluorinating 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with HF to form 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb).

17. The process of claim 14 , further comprising hydrofluorinating 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with HF to form 2,3,3,3-tetrafluoropropene (HFO-1234yf).

18. The process of claim 16 , further comprising dehydrochlorinating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) to form 2,3,3,3-tetrafluoropropene (HFO-1234yf).

19. The process of claim 16 , further comprising reacting 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) with caustic to form 2,3,3,3-tetrafluoropropene (HFO-1234yf).

20. A process of preparing 3,3,3-trifluoroprop-1-ene comprising reacting 3-chloro-1,1,1-trifluoropropane with aqueous NaOH, wherein the reacting is performed at a temperature of from about 35 ° C. to about 80° C. and at a pressure of from about 5 psig to about 230 psig, and wherein the reacting is conducted in the absence of a phase transfer catalyst and an organic solvent component.

Assignees

• Chemours Co Fc Llc

Inventors

• Sun Xuehui
• Krause Karl Robert

Classifications

• C07C19/10

  and chlorine · CPC title

• B01J27/10

  Chlorides · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C17/07

  by addition of hydrogen halides · CPC title

• C07C17/04

  to unsaturated halogenated hydrocarbons · CPC title