IP Library Granted Patent US 9,586,876
Granted Patent B2
US 9,586,876 · App. 14/318,746 · Granted Mar 7, 2017

Process for producing 2,3,3,3-tetrafluoropropene

Inventors: Haiyou Wang (Williamsville, NY); Hsueh Sung Tung (Getzville, NY); Rajiv R. Singh (Getzville, NY); Ian Shankland (Randolph, NJ)
Assignee: HONEYWELL INTERNATIONAL INC.
C07C17/25C07C17/04C07C17/383C07C17/395C07C19/08C07C21/18
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Quick Facts
Patent No.
US 9,586,876
App. No.
14/318,746
Granted
Mar 7, 2017
Kind
B2
Abstract

The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.

Claims (23)

1. A method for producing 2,3,3,3-tetrafluoropropene (1234yf) from 1,1,1,2,3-pentafluoropropane (245eb) comprising:

(a) providing a stream containing at least about 50% by weight of 245eb and at least one impurity in an amount greater than 2% by weight, wherein said impurity is selected from 1,1,1,2,3,3-hexafluoropropane (236ea) and 1,2,3,3,3-pentafluoropropene (1225ye);

(b) processing said steam provided in step (a) to produce at least one reactor feed stream by ensuring that said at least one reactor feed stream contains not more than 2% by weight of any one of the compounds 1,1,1,2,3,3-hexafluoropropane (236ea) and 1,2,3,3,3,-penatfluoropropene (1225ye), based on the total weight of 245eb in the reactor feed stream(s); and

(c) feeding at least a portion of said feed stream to at least one dehydrofluorination reactor to produce a reaction product comprising relatively more 2,3,3,3-tetrafluoropropene compared to the amount of 2,3,3,3-tetrafluoropropene in said feed stream.

2. The method of claim 1 wherein said ensuring step comprises ensuring that said at least one reactor feed stream contains not more than about 0.5% by weight of any one of the compounds 1,1,1,2,3,3-hexafluoropropane (236ea) and 1,2,3,3,3,-penatfluoropropene (1225ye), based on the total weight of 245eb in the reactor feed stream(s).

3. The method of claim 1 wherein said ensuring step comprises treating said 245fa feed stream to reduce the content of at least one of said 1,1,1,2,3,3-hexafluoropropane (236ea) and 1,2,3,3,3,-penatfluoropropene (1225ye).

4. The method of claim 3 wherein said treating step comprises subjecting said 245eb feed stream to one or more of the steps of (i) photochlorination; (ii) distillation; and (iii) liquid-liquid extraction.

5. The method of claim 4 wherein said treating step comprises subjecting said 245eb feed stream to distillation, liquid-liquid extraction, or combinations of these.

6. The method of claim 1 wherein said method produces a 1234yf product comprising not more than about 500 part per million (ppm) of 1,2,3,3,3-pentafluoropropene and not more than about 50 ppm of trifluoropropene.

7. The method of claim 1 wherein said at least one impurity in an amount greater than 2% by weight is selected from 1,1,1,2,3,3-hexafluoropropane (236ea) and 1,2,3,3,3-pentafluoropropene (1225ye) and further comprising processing said reaction product to produce a high purity 1234yf product comprising not more than about 500 part per million (ppm) of 1,2,3,3,3-pentafluoropropene and not more than about 50 ppm of trifluoropropyne.

8. A method for producing 2,3,3,3-tetrafluoropropene (1234yf) from 1,1,1,2,3-pentafluoropropane (245eb) comprising:

(a) providing a raw feed stock comprising a majority of 1,1,1,2,3-pentafluoropropane and greater than 2% by weight of one or more impurities selected from, 1,2,3,3,3-pentafluoropropene (1225ye) and 1,1,1,2,3,3-hexafluoropropane (236ea);

(b) optionally, subjecting said raw feed stock to a photochlorination;

(c) purifying said raw feed stock or said modified feed stock to produce a high purity feed stock, wherein said purifying involves a distillation and/or a liquid-liquid extraction process and wherein said high purity feed stock comprises relatively less of at least one of said impurities compared to said raw feed stock or said modified feed stock;

(d) subjecting said high purify feed stock to conditions effective to dehydrofluorinate at least a portion of said 1,1,1,2,3-pentafluoropropane to produce a reaction product comprising relatively more 2,3,3,3-tetrafluoropropane compared to said high purity feed stock; and

(e) processing said reaction product to produce a final product comprising a majority of 2,3,3,3-tetrafluoropropane, and not greater than about 500 part per million (ppm) of 1,2,3,3,3-pentafluoropropene and not greater than about 50 ppm of trifluoropropene.

9. The method of claim 8 wherein said photochlorination is not optional and involves reacting 1,2,3,3,3-pentafluoropropene with Cl 2 in presence of ultraviolet light to yield 2,3-dichloro-1,1,1,2,3-pentafluoropropane.

10. The method of claim 8 wherein said high purity feed stream comprises at least about 99.9 weight percent 1,1,1,2,3-pentafluoropropane.

11. The method of claim 8 wherein said dehydrofluorination involves contacting said high purify feed stream with at least one dehydrohalogenation agent selected from the group consisting of KOH, NaOH, Ca(OH) 2 , and CaO.

12. The method of claim 8 wherein said dehydrohalogenation agent comprises an aqueous solution.

13. The method of claim 8 wherein said dehydrofluorination involves contacting said high purity feed stock with at least one dehydrohalogenation catalyst.

14. The method of claim 8 wherein said raw feed stock comprises greater than 2% by weight of 1,2,3,3,3-pentafluoropropene (1225ye) and wherein said final product comprises from 0 to about 200 part per million of 1,2,3,3,3-pentafluoropropene.

15. The method of claim 14 herein said final product comprises from 0 to about 100 part per million of 1,2,3,3,3-pentafluoropropene.

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 4, 2025
From: WANG, HAIYOU; TUNG, HSUEH SUNG; SINGH, RAJIV R.; SHANKLAND, IAN
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 070400/0597 →
Continuity (2)
Continuation 12510740 · Jul 28, 2009
Related Publication 20140316169A1 · Oct 23, 2014