IP Library Granted Patent US 9,353,030
Granted Patent B2
US 9,353,030 · App. 14/737,530 · Granted May 31, 2016

One-step process for hexafluoro-2-butene

Inventors: Haridasan K. Nair (Williamsville, NY); David Nalewajek (West Seneca, NY); Glenn Matthies (Lockport, NY)
Assignee: Honeywell International Inc.
C07C17/361B01J21/18B01J23/462B01J23/466B01J23/755B01J27/132C07C17/26C07C17/358
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Quick Facts
Patent No.
US 9,353,030
App. No.
14/737,530
Granted
May 31, 2016
Kind
B2
Abstract

Disclosed is a one step process for making of 1,1,1,4,4,4-hexafluoro-2-butene. More specifically, the present invention provides a process for making hexafluoro-2-butene, continuously, from 2-chloro-3,3,3-trifluoropronene using Fe 2 O 3 /NiO impregnated carbon catalyst at 600° to 650° C.

Claims (18)

1. A process for making 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336) from 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) comprising reacting HCFC-1233xf with a selected catalyst, at a reactive temperature, to produce HFO-1336.

2. The process of claim 1 , which is conducted in the vapor phase.

3. The process of claim 2 , which is conducted in a continuous manner.

4. The process of claim 2 , wherein the catalyst comprises Fe 2 O 3 /NiO.

5. The process of claim 4 , wherein the catalyst comprises a ratio of about 95-99 wt % Fe 2 O 3 to about 5-1 wt % NiO.

6. The process of claim 4 , wherein the catalyst comprises a ratio of about 98 wt % Fe 2 O 3 to 2 wt % NiO.

7. The process of claim 2 , wherein the catalyst is selected from the group consisting of RuO 2 , RuO 4 , and OsO 4 in combination with oxides of Pd or Pt.

8. The process of claim 2 , wherein the catalyst is impregnated on carbon.

9. The process of claim 8 , wherein the carbon is activated carbon.

10. The process of claim 9 , wherein the activated carbon is granular with a mesh size of 4-14.

11. The process of claim 9 , wherein the activated carbon is pelletized.

12. The process of claim 2 , wherein the reaction temperature ranges from 600° to 650° C.

13. The process of claim 1 , wherein both the trans and cis isomers of HFO-1336 are formed.

14. The process of claim 13 , wherein the predominant isomer of HFO-1336 formed is the trans isomer.

15. The process of claim 14 , wherein the ratio of the trans isomer to the cis isomer of HFO-1336 is about 88:12.

16. The process of claim 15 , wherein the trans isomer is converted into the cis isomer by reaction with an isomerization catalyst.

17. The process of claim 16 , wherein the isomerization catalyst comprises a fluorinated chromia catalyst.

18. The process of claim 1 , further comprising the step of using 1,1,1,4,4,4 hexafluoro-2-butene as a foam blowing agent.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2015
From: NAIR, HARIDASAN K.; NALEWAJEK, DAVID; MATTHIES, GLENN
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 035899/0672 →
Continuity (2)
Provisional Application 62028851 · Jul 25, 2014
Related Publication 20160023972A1 · Jan 28, 2016