IP Library Granted Patent US 12,304,880
Granted Patent B2
US 12,304,880 · App. 18/079,677 · Granted May 20, 2025

Method for dehydrochlorination of HCFC-244BB to manufacture HFO-1234YF

Inventors: Haluk Kopkalli (Staten Island, NY); Carlos Navar (Baton Rouge, LA); Yuon Chiu (Denville, NJ); Haiyou Wang (Amherst, NY)
Assignee: Honeywell International Inc.
C07C17/25C07C17/38C07C17/383
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Quick Facts
Patent No.
US 12,304,880
App. No.
18/079,677
Granted
May 20, 2025
Kind
B2
Abstract

A process for making 2,3,3,3-tetrafluoropropene (HFO-1234yf) includes providing a composition including 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) to a reactor including a heater surface at a surface temperature greater than about 850° F. (454° C.), and then bringing the composition into contact with the heater surface for a contact time of less than 10 seconds to dehydrochlorinate a portion of the HCFC-244bb to make HFO-1234yf.

Claims (27)

1. A process for making 2,3,3,3-tetrafluoropropene (HFO-1234yf), the process comprising:

providing a composition including at least 96 wt. % 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) to a reactor including a heater surface at a surface temperature from about 975° F. (524° C.) to about 1,005° F. (541° C.); and

bringing the composition into contact with the heater surface for a contact time of less than 10 seconds to dehydrochlorinate a portion of the HCFC-244bb to make a final product stream comprising HFO-1234yf, wherein the HFO-1234yf includes 1,1,1,2-tetrafluoroethane (HFC-134a) at a concentration from 0.0001 wt. % to 0.010 wt. % on an HCFC-244bb-free basis.

2. The process of claim 1 , wherein the contact time is from 0.1 seconds to 9 seconds.

3. The process of claim 1 , wherein the heater surface includes a catalytic surface.

4. The process of claim 3 , wherein the catalytic surface includes electroless nickel, nickel, stainless steel, nickel-copper alloy, nickel-chromium-iron alloy, nickel-chromium alloy, nickel-chromium-molybdenum, or combinations thereof.

5. The process of claim 3 , wherein the catalytic surface comprises nickel-chromium-iron alloy.

6. The process of claim 3 , wherein the catalytic surface comprises nickel-chromium-molybdenum alloy.

7. The process of claim 1 , wherein the heater surface is not a catalytic surface.

8. The process of claim 1 , further including:

vaporizing the composition; and

heating the vaporized composition to a temperature from about 575° F. (302° C.) to 1,200° F. (649° C.) before providing the composition to the reactor.

9. The process of claim 1 , wherein the dehydrochlorination of the portion of the HCFC-244bb produces hydrogen chloride (HCl) and wherein the final product stream comprises HFO-1234yf, HCl, and unreacted HCFC-244bb, the process further comprising:

separating the HFO-1234yf and the HCl from at least a portion of the HCFC-244bb in the distillation column;

recycling the separated HCFC-244bb forming a recycle stream and combining the recycle stream with the composition forming a combined stream and providing the combined stream into the reactor including the heater surface and vaporizing the combined stream to form a vaporized composition;

providing the HFO-1234yf and the HCl to an HCl separation unit; and

separating the HCl from the HFO-1234yf to form a final product stream including the HFO-1234yf.

10. The process of claim 9 , wherein the final product stream comprises the HFO-1234yf at a concentration greater than 99.1 wt. % on an HCFC-244bb-free basis.

11. The process of claim 1 , wherein the final product stream comprises the HFO-1234yf at a concentration greater than 99.1 wt. % on an HCFC-244bb-free basis.

12. The process of claim 1 , wherein the final product stream comprises the HFO-1234yf at a concentration greater than 99.5 wt. % on an HCFC-244bb-free basis.

13. The process of claim 1 , wherein the final product stream comprises the HFO-1234yf at a concentration greater than 99.8 wt. % on an HCFC-244bb-free basis.

14. The process of claim 1 , wherein the HFO-1234yf includes 1,1,1,2-tetrafluoroethane (HFC-134a) at a concentration from 0.001 wt. % to 0.010 wt. % on an HCFC-244bb-free basis.

15. The process of claim 1 , wherein the HFO-1234yf includes 1,1,1,2-tetrafluoroethane (HFC-134a) at a concentration from 0.05 wt. % to 0.010 wt. % on an HCFC-244bb-free basis.

16. The process of claim 1 , wherein the contact time is less than 8 seconds.

17. The process of claim 1 , wherein the contact time is less than 6 seconds.

18. The process of claim 1 , wherein the contact time is less than 4 seconds.

19. The process of claim 1 , wherein the reactor comprises a tubular body enclosing electrical resistance wires.

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 12, 2025
From: KOPKALLI, HALUK; NAVAR, CARLOS; CHIU, YUON; WANG, HAIYOU
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 070491/0355 →