Methods for removing halogenated ethylene impurities in 2, 3, 3, 3-tetrafluoropropene product

• US 10,676,415 B2
• Filed: 10/12/2018
• Issued: 06/09/2020
• Est. Priority Date: 03/15/2013
• Status: Active Grant

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Wang, Haiyou, Tung, Hsueh Sung
• Primary Examiner(s): Parsa, Jafar F
• Application Number:
  US16/158,567
• Publication Number:
  US 20190047927A1
• Time in Patent Office: 606 Days
• CPC Class Codes: C07B 2200/09 Geometrical isomers
• CPC Class Codes: C07C 17/087 to unsaturated halogenated hydrocarbons
• CPC Class Codes: C07C 17/25 by splitting-off hydrogen halides from halogenated hydrocarbons
• CPC Class Codes: C07C 17/389 by adsorption on solids
• CPC Class Codes: C07C 19/10 and chlorine
• CPC Class Codes: C07C 21/18 containing fluorine
• CPC Class Codes: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

Disclosed is a composition comprised of at least one compound selected from 2,3,3,3-tetrafluoropropene, 1,3,3,3-tetrafluoro-1-propene and 1-chloro-3,3,3-trifluoropropene and halogenated impurity selected from the group consisting of HFO-1141 (CH₂═CHF), HCFO-1140 (CH₂═CHCl), and HCFO-1131 (CH₂═CFCl and/or trans/cis-CHF═CHCl) and combination thereof, said halogenated impurity being present in said composition in an amount of 50 ppm or less.

Claims

1. A composition comprised of 2,3,3,3-tetrafluoropropene and a halogenated impurity comprising CH₂═

CFCl, said halogenated impurity being present in said composition in an amount greater than 0 ppm and less than or equal to 50 ppm, wherein 2,3,3,3-tetrafluoropropene is present in said composition in at least 90% by weight.

2. The composition according to claim 1 wherein the hydrogenated impurity is present in said composition in an amount greater than 0 ppm but less than or equal to 20 ppm.

3. The composition according to claim 1 wherein the halogenated impurity is present in said composition in an amount greater than 0 ppm but less than or equal 10 ppm.

4. The composition according to claim 1 wherein one or more compounds selected from CF₃C═

CH, HFO-1243zf (CF₃CH═

CH₂), HFO-1234ze (E/Z-CF₃CH═

CHF), HCFO-1233zd (E/Z-CF₃CH═

CHCl), HCFO-1233xf (CF₃CCl═

CH₂) and combination thereof is additionally present.

5. The composition according to claim 2 wherein a compound selected from CF₃C═

CH, HFO-1243zf (CF₃CH═

CH₂), HFO-1234ze (E/Z-CF₃CH═

CHF), HCFO-1233zd (E/Z-CF₃CH═

CHCl), HCFO-1233xf (CF₃CCl═

CH₂) and combination thereof is additionally present.

6. The composition according to claim 3 wherein a compound selected from CF₃C═

CH, HFO-1243zf (CF₃CH═

CH₂), HFO-1234ze (E/Z-CF₃CH═

CHF), HCFO-1233zd (E/Z-CF₃CH═

CHCl), HCFO-1233xf (CF₃CCl═

CH₂) and combination thereof is additionally present.

7. The composition according to claim 6 wherein the compound is HFO-1243zf (CF₃CH═

CH₂), HFO-1234ze (E/Z-CF₃CH═

CHF), or HCFO-1233xf (CF₃CCl═

CH₂).

8. The composition according to claim 1 additionally comprising an additional impurity selected from the group consisting of HFO-1141 (CH₂═

CHF), HCFO-1140 (CH₂═

CHCl), and trans/cis, CHF—

CHCl and combination thereof, said CH₂═

CFCl and additional impurity being present in said composition in an amount greater than 0 ppm and less than or equal to 50 ppm.

9. The composition according to claim 8 wherein said additional impurity and CH₂═

CFCl is present in said composition in amount greater than 0 ppm and less than 20 ppm.

10. The composition according to claim 8 wherein said additional and CH₂═

CFCl is present in said composition in amount greater than 0 ppm and less than 10 ppm.

11. The composition according to claim 1 wherein 1,3,3,3-tetrafluoro-1-propene is additionally present.

12. The composition according to claim 11 which in addition comprises CH₂═

CHF.

13. A first composition comprising 2,3,3,3-tetrafluoropropene, adsorbent and halogenated impurity selected from the group consisting of HFO 1141 (CH₂═

CHF), HCFO 1140 (CH₂═

CHCl) and HCFO-1131 (CH₂═

CFCl) and/or trans/cis (CHF═

CHCl) and combination thereto, said first composition forming a second composition when separated from said absorbent, wherein the second composition comprises 2,3,3,3-tetrafluoropropene in greater than 90% by weight of said composition and said halogenated impurity is present in an amount greater than 0 ppm and less than 50 ppm.

14. The first composition according to claim 13, wherein said first composition forms a second composition when separated from said absorbent, wherein the second composition comprises 2,3,3,3-tetrafluoropropene in greater than 90% by weight of said composition and said halogenated impurity is present in an amount greater than 0 ppm and less than 20 ppm.

15. The first composition according to claim 14, wherein said first composition forms a second composition when separated from said absorbent, wherein the second composition comprises 2, 3, 3, 3-tetrafluoropropene in greater than 90% by weight of said composition and said halogenated impurity is present in an amount greater than 0 ppm and less than 10 ppm.

16. A first composition comprising 2, 3, 3, 3-tetrafluoropropene, adsorbent and halogenated impurity selected from the group consisting of HFO 1141 (CH₂═

CHF), HCFO 1140 (CH2=CHCl) and HCFO-1131 (CH₂═

CFCl) and/or trans/cis (CHF═

CHCl) and combination thereto.