IP Library Granted Patent US 10,351,494
Granted Patent B1
US 10,351,494 · App. 15/864,730 · Granted Jul 16, 2019

Systems and methods for reducing the formation of impurities during 244bb dehydrochlorination to 1234yf

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Quick Facts
Patent No.
US 10,351,494
App. No.
15/864,730
Granted
Jul 16, 2019
Kind
B1
Abstract

The present disclosure provides various manufacturing processes for the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf or 1234yf). Such methods may allow for the improved yields, more economical processes, and waste reduction in the production of 1234yf and subsequent processes.

Claims (28)

1. A method of manufacturing 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising:

providing a feed comprising 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and 1-chloro-3,3,3-trifluoropropane (HCFC-253fb);

removing the HCFC-253fb from the feed until the feed contains less than 200 ppm of the HCFC-253fb; and

dehydrochlorinating the HCFC-244bb in the feed to form a product stream containing HFO-1234yf.

2. The method of claim 1 , wherein the removing step comprises at least one of distillation, partial vaporization, partial condensing, or combinations thereof.

3. The method of claim 2 , wherein the removing step comprises continuous distillation.

4. The method of claim 1 , wherein the removing the HCFC-253fb from the feed is performed until the feed contains less than 100 ppm of the HCFC-253fb.

5. The method of claim 4 , wherein the removing the HCFC-253fb from the feed is performed until the feed contains less than 50 ppm of the HCFC-253fb.

6. A method of manufacturing 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising:

providing a feed comprising 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), HF, and 1-chloro-3,3,3-trifluoropropane (HCFC-253fb);

separating the HF and the HCFC-253fb; and

dehydrochlorinating the HCFC-244bb in the feed to form a product stream containing HFO-1234yf.

7. The method of claim 6 , wherein the separating step comprises distillation.

8. The method of claim 7 , wherein the distillation is multistage distillation.

9. The method of claim 7 , wherein at least a portion of the HCFC-253fb is separated by taking a side draw from a distillation column.

10. The method of claim 7 , wherein the distillation is continuous distillation.

11. The method of claim 6 , wherein the separating comprises at least one of decanting, centrifuging, liquid-liquid extraction, distilling, flash distilling, or combinations thereof.

12. The method of claim 6 , wherein the separating step comprises forming an azeotrope in a distillation column.

13. The method of claim 6 , further comprising, after dehydrochlorination, separating and recycling unreacted HCFC-244bb.

14. A method of manufacturing 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising:

providing a feed comprising 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and 1-chloro-3,3,3-trifluoropropane (HCFC-253fb);

dehydrochlorinating the HCFC-244bb in the feed to form a product stream containing HFO-1234yf; and

controlling the formation of vinyl chloride (1140), 3,3,3-trifluoropropene (HFO-1243zf), or combinations thereof at or below a predetermined threshold, wherein the controlling the formation 1140, HFO-1243zf, or combinations thereof includes removal of HCFC-253fb prior to the dehydrochlorinating step.

15. The method of claim 14 , wherein the predetermined threshold is about 300 ppm.

16. The method of claim 14 , wherein the removal of HCFC-253fb is performed until the feed has less than 200 ppm of HCFC-253fb.

17. The method of claim 14 , wherein the formation of vinyl chloride (1140) is controlled below 200 ppm.

18. The method of claim 14 , wherein the formation of 3,3,3-trifluoropropene (HFO-1243zf) is controlled below 200 ppm.

19. The method of claim 2 , wherein the distillation comprises removal of the HCFC-244bb from a side-draw.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074343/0989 →
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 Jan 10, 2018
From: WANG, HAIYOU; YANG, TERRIS; MERKEL, DANIEL C.; KOPKALLI, HALUK; CERRI, GUSTAVO; CHIU, YUON; HORWATH, RICHARD D.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 044588/0293 →