Process for the production of fluorinated cyclobutane

Patent metadata

Field	Value
Publication number	US-10005705-B2
Application number	US-201715807033-A
Country	US
Kind code	B2
Filing date	Nov 8, 2017
Priority date	Nov 12, 2015
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

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.

First claim

The invention claimed is:

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.

Assignees

• Honeywell Int Inc

Inventors

• Nair Haridasan K
• Banavali Rajiv
• Zhai Yian
• Matthies Glenn

Classifications

• C07C2601/04

  with a four-membered ring · CPC title

• C07C17/275 Primary

  of hydrocarbons and halogenated hydrocarbons · CPC title

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title