IP Library Granted Patent US 10,005,705
Granted Patent B2
US 10,005,705 · App. 15/807,033 · Granted Jun 26, 2018

Process for the production of fluorinated cyclobutane

Inventors: Haridasan K. Nair (Williamsville, NY); Rajiv Banavali (Morristown, NJ); Yian Zhai (Lockport, NY); Glenn Matthies (Lockport, NY)
Assignee: Honeywell International Inc.
C07C17/275C07C2601/04
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Quick Facts
Patent No.
US 10,005,705
App. No.
15/807,033
Granted
Jun 26, 2018
Kind
B2
Abstract

The production of 1, 1, 2-trifluoro-2-(trifluoromethyl)cyclobutane (TFMCB). More specifically, the present invention relates to a process for making 1, 1, 2-trifluoro-2-(trifluoromethyl)cyclobutane via a continuous catalytic reaction from commercially available raw materials ethylene and hexafluoropropene.

Claims (28)

1. A process for producing 1,1,2-trifluoro-2-(trifluoromethyl)cyclobutane (TFMCB), comprising the following steps:

introducing hexafluoropropene and ethylene into a reaction vessel; and

reacting the hexafluoropropene and ethylene in the reaction vessel in the presence of at least one oligomerization/polymerization (OP) inhibitor and at least one metal catalyst.

2. The process of claim 1 , wherein the process is a continuous process and further comprises the additional steps, following the reacting step, of:

removing TFMCB product from the reaction vessel; and

repeating said introducing, reacting and removing steps (a) through (c).

3. The process of claim 1 , further comprising the additional steps, following the reacting step, of:

removing at least one of unreacted hexafluoropropene and unreacted ethylene from the reaction vessel; and

recycling the at least one of unreacted hexafluoropropene and unreacted ethylene back into the reaction vessel.

4. The process of claim 1 , further comprising the additional steps, following the reacting step, of:

removing unreacted hexafluoropropene and unreacted ethylene from the reaction vessel; and

recycling the unreacted hexafluoropropene and unreacted ethylene back into the reaction vessel.

5. The process of claim 1 , wherein the metal catalyst is selected from the group consisting of nickel and nickel-based alloys.

6. The process of claim 1 , wherein the oligomerization/polymerization (OP) inhibitor comprises at least one gas phase compound selected from the group consisting of nitric oxide (NO), nitrogen dioxide (NO 2 ), carbon monoxide (CO) and sulphur dioxide (SO 2 ).

7. The process of claim 1 , wherein the oligomerization/polymerization (OP) inhibitor is 2,2,6,6-tetramethylpiperidinyl-1-oxl.

8. The process of claim 1 , wherein the oligomerization/polymerization (OP) inhibitor is selected from the group consisting of catechol and catechol derivatives, terpenes, quinones and combinations thereof.

9. The process of claim 1 , wherein the oligomerization/polymerization (OP) inhibitor is present at from about 50 ppm to about 2,000 ppm by weight based on the total weight of the reaction composition in the reaction vessel.

10. The process of claim 1 , wherein the oligomerization/polymerization (OP) inhibitor is present at from about 500 ppm to about 1,000 ppm based on the total weight of the reaction composition in the reaction vessel.

11. The process of claim 1 , wherein the reacting step is conducted at a pressure between 600 psig and 1500 psig.

12. The process of claim 1 , wherein the reacting step is conducted at a pressure between 800 psig and 1200 psig.

13. The process of claim 1 , wherein the reacting step is conducted at a temperature between 300° C. and 500° C.

14. The process of claim 1 , wherein the reacting step is conducted at a temperature between 300° C. and 400° C.

15. The process of claim 1 , wherein during the reacting step, the hexafluoropropene and ethylene are present at a molar ratio of from 1:1 to 1:6.

16. The process of claim 6 , wherein the metal catalyst is selected from the group consisting of nickel and nickel-based alloys.

17. The process of claim 5 , wherein the oligomerization/polymerization (OP) inhibitor comprises at least one gas phase compound selected from the group consisting of nitric oxide (NO), nitrogen dioxide (NO 2 ), carbon monoxide (CO) and sulphur dioxide (SO 2 ).

18. The process of claim 17 , wherein the oligomerization/polymerization (OP) inhibitor is 2,2,6,6-tetramethylpiperidinyl-1-oxl.

19. The process of claim 17 , wherein the oligomerization/polymerization (OP) inhibitor is selected from the group consisting of catechol and catechol derivatives, terpenes, quinones and combinations thereof.

20. The process of claim 19 , wherein the oligomerization/polymerization (OP) inhibitor is present at from about 50 ppm to about 2,000 ppm by weight based on the total weight of the reaction composition in the reaction vessel.

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 Nov 8, 2017
From: NAIR, HARIDASAN K.; BANAVALI, RAJIV; ZHAI, YIAN; MATTHIES, GLENN
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 044075/0297 →
Continuity (5)
Continuation PCTUS2017060394 · Nov 7, 2017
Continuation In Part 15582981 · May 1, 2017
Continuation In Part 15345695 · Nov 8, 2016
Provisional Application 62254338 · Nov 12, 2015
Related Publication 20180065905A1 · Mar 8, 2018
Cited By (2)
US 12,281,053 US 12,304,880