IP Library Granted Patent US 9,394,217
Granted Patent B2
US 9,394,217 · App. 14/206,100 · Granted Jul 19, 2016

Staged fluorination process and reactor system

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Quick Facts
Patent No.
US 9,394,217
App. No.
14/206,100
Granted
Jul 19, 2016
Kind
B2
Abstract

The invention relates to a process to produce 244bb from 1233xf in multiple reaction zones whereby the 1233xf starting material is at least 95% converted to 244bb and by-product such as 245cb forms in amounts less than about 2%.

Claims (27)

1. A process to prepare 2-chloro-1,1,1,2-tetrafluoropropane (244bb) comprising contacting 2-chloro-3,3,3,-trifluoropropene (1233xf) with HF in the presence of a fluorination catalyst in multiple reaction zones under conditions effective to produce a composition that comprises 244bb and less than about 2% by weight 1, 1, 1, 2, 2-pentafluoropropane (245cb).

2. The process of claim 1 wherein the composition produced comprises less than about 1% by weight 245cb.

3. The process of claim 1 wherein the composition produced further comprises less than about 5% by weight of unreacted 1233xf.

4. The process of claim 3 wherein the composition produced further comprises less than about 2% by weight of unreacted 1233xf.

5. The process of claim 1 wherein more than about 95% of the 1233xf is converted to 244bb.

6. The process of claim 5 wherein more than about 98% of the 1233xf is converted to 244bb.

7. The process of claim 1 wherein the multiple reaction zones comprise multiple reactors operated in series.

8. The process of claim 7 wherein the multiple reactors comprise at lease least first and second reactors operated in series.

9. The process of claim 1 wherein the fluorination catalyst is selected from the group consisting of Lewis acids, transition metal halides, transition metal oxides, Group IVb metal halides, a Group Vb metal halides, or combinations thereof.

10. The process of claim 9 wherein the fluorination catalyst is select from the group consisting of SbCl 5 , SbCl 3 , SbF 5 , SnCl 4 , TaCl 5 , TiCl 4 , NbCl 5 , MoCl 6 , FeCl 3 , a fluorinated species of SbCl 5 , a fluorinated species of SbCl 3 , a fluorinated species of SnCl 4 , a fluorinated species of TaCl 5 , a fluorinated species of TiCl 4 , a fluorinated species of NbCl 5 , a fluorinated species of MoCl 6 , a fluorinated species of FeCl 3 , or combinations thereof.

11. The process of claim 1 wherein the fluorination catalyst is the same or different in each of the multiple reaction zones.

12. A process to prepare 2-chloro-1,1,1,2-tetrafluoropropane (244bb) comprising:

a) contacting, in a first reaction zone, feed 2-chloro-3,3,3,-trifluoropropene (1233xf) with HF and first fluorination catalyst under conditions effective to produce a first composition comprising unreacted 1233xf, a first amount of 2-chloro-1,1,1,2-tetrafluoropropane (244bb), and a first amount of 1,1,1,2,2-pentafluoropropane (245cb);

b) contacting, in a second reaction zone, the first composition with a second fluorination catalyst under conditions to produce a second composition, wherein the second composition comprises 244bb, and less than about 5% 1233xf by weight relative to the amount of feed 1233xf, and less than about 2% by weight 245cb.

13. The process of claim 12 wherein the second reaction zone is comprised of one or more reactors operated in series.

14. The process of claim 12 wherein the first and the second reaction zones each comprise CSTR reactors.

15. The process of claim 12 wherein said first composition further comprises carryover first fluorination catalyst which is removed from the first composition prior to contacting in said second reaction zone.

16. The process of claim 12 wherein the first and second fluorination catalysts each comprise a fluorinated SbCl 5 species.

17. A process to prepare 2,3,3,3-tetrafluoropropene (1234yf) comprising:

a) providing a starting composition comprising at least one compound having a structure selected from Formula I, II and II:

CX 2 ═CCl—CH 2 X  (Formula I)

CX 3 —CCl═CH2  (Formula II)

CX 3 —CHCl—CH 2 X  (Formula III)

 wherein X is independently selected from F, Cl, Br and I, provided that at least one of X is not F;

b) contacting said starting composition with HF under conditions effective to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene (1233xf);

c) contacting said first intermediate composition comprising 1233xf with HF in the presence of a fluorination catalyst in multiple reaction zones under conditions effective to produce a second intermediate composition comprising 244bb and less than about 2% by weight 1,1,1,2,2-pentafluoropropane (245cb); and

d) dehydrochlorinating at least a portion of said 244bb to produce a reaction product comprising 1234yf.

Assignments (2)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 14, 2014
From: CHIU, YUON; SMITH, ROBERT A.; KOPKALLI, HALUK; MERKEL, DANIEL C.
To: HONEYWELL INTERNATIONAL, INC.
Reel/Frame 032885/0801 →