IP Library Granted Patent US 11,555,001
Granted Patent B2
US 11,555,001 · App. 16/972,473 · Granted Jan 17, 2023

Method for dehydrochlorination of HCFC-244bb to manufacture HFO-1234yf

Inventors: Haluk Kopkalli (Morris Plains, NJ); Carlos Navar (Morris Plains, NJ); Yuon Chiu (Morris Plains, NJ); Haiyou Wang (Morris Plains, NJ)
Assignee: Honeywell International Inc.
C07C17/25C07C17/38C07C17/383
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Quick Facts
Patent No.
US 11,555,001
App. No.
16/972,473
Granted
Jan 17, 2023
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 (22)

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);

vaporizing the composition;

heating the vaporized composition before providing the composition to a reactor including a heater surface at a surface temperature from about 870° F. (466° C.) to about 1200° F. (649° 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 HFO-1234yf forming a product stream, and

providing the product stream from the reactor to a distillation column;

wherein heating the vaporized composition includes exchanging heat between the vaporized composition and the product stream from the reactor before providing the product stream to the distillation column.

2. The process of claim 1 , wherein the heater surface is at a surface temperature from about 940° F. (504° C.) to about 1,005° F. (541° C.).

3. The process of claim 2 , wherein the HFO-1234yf includes 1,1,1,2-tetrafluoroethane at a concentration less than 0.1 wt. % on an HCFC-244bb-free basis as an indication of a low rate of carbon build-up in the reactor.

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

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

6. The process of claim 5 , 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.

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 product stream comprises HFO-1234yf, HCl, and unreacted HCFC-244bb, the process further including:

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 includes the HFO-1234yf at a concentration greater than 99.1 wt. % on an HCFC-244bb-free basis.

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 Nov 3, 2021
From: KOPKALLI, HALUK; NAVAR, CARLOS; CHIU, YUON; WANG, HAIYOU
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 058011/0165 →