IP Library Granted Patent US 9,272,968
Granted Patent B2
US 9,272,968 · App. 13/826,627 · Granted Mar 1, 2016

Process to suppress the formation of 3,3,3-trifluoropropyne in fluorocarbon manufacture

Inventors: Haluk Kopkalli (Staten Island, NY); Jeffrey A. Ball (Randolph, NJ); Yuon Chiu (Denville, NJ); Hsueh Sung Tung (Getzville, NY); Konstantin A. Pokrovski (Orchard Park, NY); Daniel C. Merkel (West Seneca, NY)
Assignee: Honeywell International Inc.
C07C17/38C07B2200/09C07C17/206C07C17/25C07C17/383C07C17/389
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Quick Facts
Patent No.
US 9,272,968
App. No.
13/826,627
Granted
Mar 1, 2016
Kind
B2
Abstract

This invention relates to a process for the suppression of 3,3,3-trifluoropropyne during the manufacture of fluorocarbons, fluoroolefins, hydrochlorofluoroolefins. More particularly, this invention is directed to a process to suppress the formation of 3,3,3-trifluoropropyne during processes for the manufacture of HCFO-1233zd(E), HCFO-1233zd(Z), HFO-1234ze(E), and/or HFO-1234ze(Z).

Claims (28)

1. A process for preventing the formation of 3,3,3-trifluoropropyne during the manufacture of fluorocarbon compounds, said method comprising the steps of:

(a) forming a fluorocarbon compound selected from the group consisting of HCFO-1233zd(Z) and HFO-1234ze(Z) in a reaction process that generates reaction products comprising one or more acids;

(b) conducting one or more substantially caustic-free bulk acid removal procedures on the reaction products of step (a);

wherein the bulk removal of the acids in step (b) comprises treating the reaction products with a first scrubber solution in a first absorber to remove the bulk of the acid; and

(c) conducting one or more trace acid removal procedures to remove acids remaining after step (b); and

whereby the formation of 3,3,3-trifluoropropyne is prevented by the removal of acid during the process.

2. The process of claim 1 , wherein the bulk removal of the acids in step (b) further comprises one or more purification techniques selected from distillation, extraction, and decantation.

3. The process of claim 1 , wherein the first scrubber solution comprises water.

4. The process of claim 1 , wherein the acid being removed is HF and the first scrubber solution comprises a weak HF solution.

5. The process of claim 1 , wherein the first scrubber solution comprises H 2 SO 4 .

6. The process of claim 1 , whereby in step (c) the reaction products of step (b) are treated in a second absorber with a second scrubber solution to remove further amounts of acid.

7. The process of claim 6 , wherein the second scrubber solution comprises water.

8. The process of claim 6 , wherein the second scrubber solution comprises H 2 SO 4 .

9. The process of claim 1 , wherein step (b) comprises a liquid phase deacidification process, using water to absorb and remove the bulk of the acid.

10. The process of claim 9 , wherein the step (b) process is conducted in batch mode.

11. The process of claim 10 , wherein the step (b) process is conducted in a single stage.

12. The process of claim 10 , wherein the step (b) process is conducted in multiple stages.

13. The process of claim 10 , wherein the step (b) process is conducted in continuous mode.

14. The process of claim 13 , wherein the step (b) process is conducted in a single stage.

15. The process of claim 13 , wherein the step (b) process is conducted in multiple stages.

16. The process of claim 10 , wherein the step (b) process further comprises a continuous extraction procedure.

17. A process for preventing the formation of 3,3,3-trifluoro-propyne during the manufacture of fluorocarbon compounds, said method comprising the steps of:

(a) forming a fluorocarbon compound selected from the group consisting of HCFO-1233zd(Z) and HFO-1234ze(Z) in a reaction process that generates reaction products comprising one or more acids;

(b) conducting one or more substantially caustic-free bulk acid removal procedures on the reaction products of step (a);

wherein the bulk removal of the acids in step (b) comprises treating the reaction products with a first scrubber solution selected from water and an aqueous HF solution in a first absorber to remove the bulk of the acid; and

(c) conducting one or more trace acid removal procedures to remove acids remaining after step (b);

wherein in step (c) the reaction products of step (b) are treated in a second absorber with a second scrubber solution selected from water and H 2 SO 4 to remove further amounts of acid; and

whereby the formation of 3,3,3-trifluoropropyne is prevented by the removal of acid during the process.

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 14, 2013
From: KOPKALLI, HALUK; BALL, JEFFREY A.; CHIU, YUON; TUNG, HSUEH SUNG; MERKEL, DANIEL C.; POKROVSKI, KONSTANTIN A.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 029999/0505 →
Continuity (1)
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