Process for reducing 3,3,3-trifluoropropyne in 2,3,3,3-tetrafluoropropene

Patent metadata

Field	Value
Publication number	US-10913697-B2
Application number	US-201716346739-A
Country	US
Kind code	B2
Filing date	Nov 2, 2017
Priority date	Nov 2, 2016
Publication date	Feb 9, 2021
Grant date	Feb 9, 2021

Abstract

The invention relates to a process for reducing the concentration of a fluorinated alkyne impurity, such as 3,3,3-trifluoropropyne (TFPY), in 2,3,3,3-tetrafluoropropene (HFO-1234yf) which comprises contacting such a mixture with a caustic material, such as sodium hydroxide (NaOH), under conditions effective to reduce the concentration of the fluorinated alkyne impurity, including in some practices reducing the concentration by at least about 50%.

First claim

What is claimed is:

1. A process for producing purified 2,3,3,3-tetrafluoropropene, the process comprising reducing the concentration of a fluorinated alkyne impurity in 2,3,3,3-tetrafluoropropene (HFO-1234yf) by contacting a mixture comprising HFO-1234yf and at least one fluorinated alkyne impurity having the formula RC≡CH, wherein R is a perfluorinated straight chain C 1 -C 3 alkyl, with a caustic material under conditions effective whereby at least one reaction product between the caustic material and at least a portion of the alkyne impurity is formed, and whereby the HFO-1234yf remains substantially unreacted.

2. The process of claim 1 further comprising recovering the HFO-1234yf having the reduced concentration of said fluorinated alkyne impurity.

3. The process of claim 1 wherein R is —CF 3 .

4. The process of claim 1 wherein the caustic material is selected from the group consisting of an alkali metal hydroxide, an alkali metal oxide, an alkali earth metal hydroxide, an alkali earth metal oxide, and combinations thereof.

5. The process of claim 4 wherein the alkali metal hydroxide is selected from the group consisting of potassium hydroxide (KOH), sodium hydroxide (NaOH), lithium hydroxide (LiOH), cesium hydroxide (CsOH), rubidium hydroxide (RbOH), and combinations thereof.

6. The process of claim 4 wherein the alkali earth metal hydroxide is selected from the group consisting of magnesium hydroxide (Mg(OH) 2 ), calcium hydroxide (Ca(OH) 2 ), strontium hydroxide (Sr(OH) 2 ), barium hydroxide (Ba(OH) 2 ), and combinations thereof.

7. The process of claim 4 wherein the alkali earth metal oxide is calcium oxide (CaO).

8. The process of claim 1 wherein the caustic material is present in an aqueous solution at less than about 50% by weight of the caustic material.

9. The process of claim 8 wherein the caustic material is present in an aqueous solution at between about 0.1% to about 20% by weight of the caustic material.

10. The process of claim 9 wherein the caustic material is present in an aqueous solution at between about 2% to about 5% by weight of the caustic material.

11. The process of claim 10 wherein the caustic material is NaOH.

12. The process of claim 1 wherein the concentration of the fluorinated alkyne impurity is reduced by at least about 20%.

13. The process of claim 12 wherein the concentration of the fluorinated alkyne impurity is reduced by at least about 50%.

14. A process for reducing the concentration of 3,3,3-trifluoropropyne (TFPY) in 2,3,3,3-tetrafluoropropene (HFO-1234yf) which comprises:
(a) providing a first composition comprising 2,3,3,3-tetrafluoropropene (HFO-1234yf) and a first concentration of 3,3,3-trifluoropropyne (TFPY);
(b) contacting the first composition with a caustic material under conditions effective to react the caustic material with at least a portion of the TFPY; and
(c) recovering a second composition comprising 1234yf and a second concentration of TFPY, the second concentration being less than the first concentration.

15. The process of claim 14 wherein first concentration of TFPY is greater than 300 ppm.

16. The process of claim 14 wherein the second concentration of TFPY is 300 ppm or less.

17. The process of claim 16 wherein the second concentration of TFPY is about 100 ppm or less.

18. The process of claim 14 wherein the caustic material comprises NaOH.

19. The process of claim 18 wherein the NaOH is provided as aqueous solution of about 0.1% to about 20% NaOH by weight.

20. The process of claim 19 wherein the NaOH is provided as aqueous solution of about 4% NaOH by weight.

Assignees

• Honeywell Int Inc

Inventors

• Wang Haiyou
• Tung Hsueh Sung
• Perez Willie Josue
• Zhai Yian
• Borowski Ralph John
• Tu Fang Huang
• Labuda Lucas Peter
• Welch John L

Classifications

• C07C17/395 Primary

  by treatment giving rise to a chemical modification of at least one compound · CPC title

• C07C17/25

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• C07C17/206

  the other compound being HX · CPC title

• C07C17/087

  to unsaturated halogenated hydrocarbons · CPC title

• B01D53/28

  Selection of materials for use as drying agents · CPC title