IP Library Granted Patent US 8,058,486
Granted Patent B2
US 8,058,486 · App. 12/404,130 · Granted Nov 15, 2011

Integrated process to produce 2,3,3,3-tetrafluoropropene

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Quick Facts
Patent No.
US 8,058,486
App. No.
12/404,130
Granted
Nov 15, 2011
Kind
B2
Abstract

A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX 2 ═CCl—CH 2 X  (Formula I) CX 3 —CCl═CH 2   (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 X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.

Claims (27)

1. A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising:

a. providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III:

CX 2 ═CCl—CH 2 X  (Formula I)

CX 3 —CCl═CH 2   (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 X is not fluorine;

b. contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct;

c. contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane; and

d. dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene and a second chlorine-containing byproduct.

2. The method of claim 1 further comprising the step of removing at least a portion of said first chlorine-containing byproduct from said first intermediate composition subsequent to, and/or concurrently with, said contacting step (b).

3. The method of claim 2 further comprising the step of removing at least a portion of said second chlorine-containing byproduct from said product subsequent to, and/or concurrently with, said step (d).

4. The method of claim 1 wherein at least one X is chlorine.

5. The method of claim 4 wherein a majority of X is chlorine.

6. The method of claim 5 wherein said compound according to Formula I is 1,1,2,3-tetrachloropropene.

7. The method of claim 5 wherein said compound according to Formula II is 2,3,3,3-tetrachloropropene.

8. The method of claim 5 wherein said compound according to Formula III is 1,1,1,2,3-pentachloropropane.

9. The method of claim 1 wherein said first and second chlorine-containing byproducts comprise hydrogen chloride.

10. The method of claim 1 wherein said contacting step (b) comprises a vapor-phase catalytic fluorination of said compound having a structure according to Formulae I, II, or III.

11. The method of claim 10 wherein said first fluorinating agent is hydrogen fluoride.

12. The method of claim 11 further comprising the step of separating at least a portion of said hydrogen fluoride from said 2-chloro-3,3,3-trifluoropropene subsequent to, or concurrently with, step (b) and prior to step (c).

13. The method of claim 12 wherein said first fluorinating agent comprises at least a portion of said hydrogen fluoride separated from said 2-chloro-3,3,3-trifluoropropene.

14. The method of claim 1 wherein said contacting step (c) comprises a liquid-phase fluorination of said 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst.

15. The method of claim 14 wherein said second fluorinating agent is hydrogen fluoride.

16. The method of claim 15 wherein further comprising the step of separating at least a portion of said hydrogen fluoride from said 2-chloro-1,1,1,2-tetrafluoropropane subsequent to, or concurrently with, step (c) and prior to step (d).

17. The method of claim 16 wherein said second fluorinating agent comprises at least a portion of said hydrogen fluoride separated from said 2-chloro-1,1,1,2-tetrafluoropropane.

18. The method of claim 1 wherein said dehydrochlorination is conducted in the vapor phase and in the presence of a catalyst.

19. The method of claim 1 wherein said 2,3,3,3-tetrafluoroprop-1-ene is separated from said reaction product via at least one distillation operation.

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 Mar 16, 2009
From: MERKEL, DANIEL C.; TUNG, HSUEH SUNG; POKROVSKI, KONSTANTIN A.; BEKTESEVIC, SELMA; JOHNSON, ROBERT; WANG, HAIYOU
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 022402/0607 →