IP Library › Granted Patent US 9,701,599
Granted Patent B2
US 9,701,599 · App. 15/190,828 · Granted Jul 11, 2017

Process for producing 2,3,3,3-tetrafluoropropene

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 9,701,599
App. No.
15/190,828
Granted
Jul 11, 2017
Kind
B2
Abstract

The invention relates to a process to prepare 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) or 2-chloro-1,1,12-tetrafluoropropane (HCFC-244bb) using dichloro-trifluoropropanes and/or trichloro-difluoropropanes, and to prepare 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) using various 242 and 243 isomers.

Claims (16)

1. A process to prepare 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) comprising contacting a compound selected from the group consisting of a dichloro-trifluoropropane, a trichloro-difluoropropane, and combinations thereof, with anhydrous hydrogen fluoride (HF) under conditions effective to produce HCFC-244bb, in the presence of a fluorination catalyst consisting of the group consisting of metal oxide, metal hydroxide, metal halide, metal oxyhalide, and mixtures thereof, wherein the metal is selected from the group consisting of chromium, aluminum, cobalt, manganese, nickel and iron and mixtures thereof.

2. The process of claim 1 wherein the dichloro-trifluoropropane is selected from the group consisting of 2,2-dichloro-1,1,1-trifluoropropane (HCFC-243ab), 1,2-dichloro-1,1,2-trifluoropropane (HCFC-243bc), 2,3-dichloro-1,1,1-trifluoropropane (HCFC-243db) and combinations thereof.

3. The process of claim 1 wherein the process occurs in a vapor phase.

4. The process of claim 1 wherein the catalyst is selected from the group consisting of Cr 2 O 3 , FeCl 3 /C, Cr 2 O 3 /Al 2 O 3 , Cr 2 O 3 /AlF 3 , Cr 2 O 3 /carbon, CoCl 2 /Cr 2 O 3 /Al 2 O 3 , NiCl 2 /Cr 2 O 3 /Al 2 O 3 , CoCl 2 /AlF 3 , NiCl 2 /AlF 3 and combinations thereof.

5. The process of claim 1 wherein the contacting occurs at a temperature between about 150° C. and about 500° C.

6. The process of claim 1 wherein the contacting occurs at a pressure of between about 20 psig and about 200 psig.

7. A process to prepare 2-chloro-1,1,1,2-tetrafluorpropane (244bb) comprising contacting 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) with HF in a reaction zone under conditions effective to form a composition comprising 244bb and 1,1,1-trifluoro-2,2-dichloropropane (243ab); contacting the 243ab with a dehydrochlorination catalyst selected from the group consisting of carbon solids, metal halides, halogenated metal oxides, zero metals and combinations thereof under conditions effective to form 1233xf; and recycling the formed 1233xf to the reaction zone.

8. The process of claim 1 wherein the trichloro-difluoropropane is selected from the group consisting of 1,2,2-trichloro-1,1-difluoropropane (HCFC-242ac), 1,1,2-trichloro-1,2-difluoropropane (HCFC-242bc), 1,2,3-trichloro-1,1-difluoropropane (HCFC-242dc) and combinations thereof.

9. A process to prepare 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) comprising contacting a compound selected from the group consisting of a trichloro-difluoropropane, and combinations thereof, with anhydrous hydrogen fluoride (HF) under conditions effective to produce HCFC-244bb, wherein the trichloro-difluoropropane is selected from the group consisting of 1,2,2-trichloro-1,1-difluoropropane (HCFC-242ac), 1,1,2-trichloro-1,2-difluoropropane (HCFC-242bc), 1,2,3-trichloro-1,1-difluoropropane (HCFC-242dc) and combinations thereof.

10. The process of claim 9 wherein the process occurs in a vapor phase.

11. The process of claim 9 wherein the contacting occurs in the presence of a catalyst.

12. The process of claim 9 wherein the catalyst is selected from the group consisting of Cr 2 O 3 , FeCl 3 /C, Cr 2 O 3 /Al 2 O 3 , Cr 2 O 3 /AlF 3 , Cr 2 O 3 /carbon, CoCl 2 /Cr 2 O 3 /Al 2 O 3 , NiCl 2 /Cr 2 O 3 /Al 2 O 3 , CoCl 2 /AlF 3 , NiCl 2 /AlF 3 and combinations thereof.

13. The process of claim 9 wherein the contacting occurs at a temperature between about 150° C. and about 500° C.

14. The process of claim 9 wherein the contacting occurs at a pressure of between about 20 psig and about 200 psig.

15. A process to prepare 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) which comprises contacting 2-chloro-3,3,3-trifluoropropene (HCO-1233x) with HF in a first reaction zone under conditions effective to form a composition comprising 244bb and dichlorotrifluoropropane 243 isomer and recycling the dichlorotrifluoropropane 243isomer to a second reaction zone wherein said dichlorotrifluoropropane 243 isomer is contacted with HF under effective conditions to form 2-chloro-3,3,3-trifluoropropane and contacting 2-chloro-3,3,3-trifluoropropane with HF in the presence of a fluorination catalyst under conditions effective to form 2-chloro-1,1,1,2-tetrafluoropropane.

16. The process according to claim 15 wherein s dichlorotrifluoropropane 243 isomer is 2,3-dichloro-1,1,1-trifluoropropane.

Assignments (1)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →