IP Library Granted Patent US 10,618,861
Granted Patent B2
US 10,618,861 · App. 16/514,241 · Granted Apr 14, 2020

Stabilization of 1-chloro-3,3,3-trifluoropropene

Inventors: Wissam Rached (Chaponost, FR); Sophie Guerin (Francheville, FR); Pascale Kindler (Fontaines sur Saone, FR)
Assignee: ARKEMA FRANCE
C07C17/42C09K5/044F01K25/10C09K2205/12
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Quick Facts
Patent No.
US 10,618,861
App. No.
16/514,241
Granted
Apr 14, 2020
Kind
B2
Abstract

The use of a C 3 to C 6 alkene compound including a sole double bond, for limiting or preventing the isomerization of trans-1-chloro-3,3,3-trifluoropropene to cis-1-chloro-3,3,3-trifluoropropene. Also, a composition including 1-chloro-3,3,3-trifluoropropene and a C 3 to C 6 alkene compound including a sole double bond, and also to various uses of this composition, such as a process for heating or cooling a fluid.

Claims (36)

1. A process for heating or cooling a fluid or a body with a vapor compression system containing a heat-transfer fluid, said process comprising, successively:

evaporating the heat-transfer fluid,

compressing the heat-transfer fluid,

condensing the heat-transfer fluid, and

expanding the heat-transfer fluid,

wherein the heat-transfer fluid is a composition comprising 1-chloro-3,3,3-trifluoropropene and a mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

2. The process of claim 1 , wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 100° C.

3. The process of claim 1 , wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 140° C.

4. The process of claim 1 , wherein the vapor compression system comprises a heat pump, wherein the heat-transfer fluid is at a temperature of at least 140° C. over at least 50% of its complete circulation time.

5. The process of claim 1 , wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 200° C.

6. The process of claim 1 , wherein the process is a cooling process.

7. The process of claim 1 , wherein the composition comprises from 0.01% to 5% of the mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

8. The process of claim 1 , wherein the composition comprises from 0.2% to 1% of the mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

9. The process of claim 1 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 90%.

10. The process of claim 1 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 99%.

11. The process of claim 1 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 99.9%.

12. The process of claim 1 , wherein the composition further comprises one or more heat-transfer compounds other than 1-chloro-3,3,3-trifluoropropene and/or one or more additives chosen from stabilizers other than the alkene compound, lubricants, surfactants, tracers, fluorescent agents, odorous agents, solubilizing agents, and mixtures thereof.

13. The process of claim 1 , wherein the composition is free of lubricant.

14. A process for producing electricity with a thermal engine, said process comprising, successively:

evaporating the heat-transfer fluid,

expanding the heat-transfer fluid in a turbine,

condensing the heat-transfer fluid, and

compressing the heat-transfer fluid,

wherein the heat-transfer fluid is a composition comprising 1-chloro-3,3,3-trifluoropropene and a mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

15. The process of claim 14 , wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 100° C.

16. The process of claim 14 , wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 140° C.

17. The process of claim 14 , wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 200° C.

18. The process of claim 14 , wherein the composition comprises from 0.01% to 5% of the mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

19. The process of claim 14 , wherein the composition comprises from 0.2% to 1% of the mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

20. The process of claim 14 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 90%.

21. The process of claim 14 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 99%.

22. The process of claim 14 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 99.9%.

23. The process of claim 14 , wherein the composition further comprises one or more heat-transfer compounds other than 1-chloro-3,3,3-trifluoropropene and/or one or more additives chosen from stabilizers other than the alkene compound, lubricants, surfactants, tracers, fluorescent agents, odorous agents, solubilizing agents, and mixtures thereof.

24. The process of claim 14 , wherein the composition is free of lubricant.

25. A composition comprising 1-chloro-3,3,3-trifluoropropene and a mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

26. The composition of claim 25 , comprising from 0.01% to 5% of the mixture comprising 2-methylbut-1-ene and 2-methylbut-2-ene.

Assignments (3)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
CORRECTIVE ASSIGNMENT TO CORRECT THE EXECUTION DATES FOR INVENTORS SOPHIE GUERIN AND PASCALE KINDLER PREVIOUSLY RECORDED ON REEL 049778 FRAME 0583. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Feb 27, 2020
From: RACHED, WISSAM; GUERIN, SOPHIE; KINDLER, PASCALE
To: ARKEMA FRANCE
Reel/Frame 052045/0980 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 17, 2019
From: RACHED, WISSAM; GUERIN, SOPHIE; KINDLER, PASCALE
To: ARKEMA FRANCE
Reel/Frame 049778/0583 →