IP Library Granted Patent US 10,399,918
Granted Patent B2
US 10,399,918 · App. 15/878,794 · Granted Sep 3, 2019

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 10,399,918
App. No.
15/878,794
Granted
Sep 3, 2019
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 (38)

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 C3 to C6 alkene compound comprising a sole double bond, selected from the group consisting of but-1-ene, cis-but-2-ene, trans-but-2-ene, 2-methylprop-1-ene, pent-1-ene, cis-pent-2-ene, trans-pent-2-ene, 2-methylbut-1-ene, 2-methylbut-2-ene and 3-methylbut-1-ene,

wherein the heat transfer fluid is at a temperature, at at least one point, greater than or equal to 100° C.

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 140° C.

3. 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.

4. 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.

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

6. The process of claim 1 , wherein the alkene is a butene or a pentene.

7. The process of claim 1 , wherein the alkene is a pentene.

8. The process of claim 1 , wherein the composition comprises from 0.01% to 5% of alkene compound.

9. The process of claim 1 , wherein the composition comprises from 0.2% to 1% of alkene compound.

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 90%.

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%.

12. 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%.

13. 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.

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

15. 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 C3 to C6 alkene compound comprising a sole double bond, selected from the group consisting of but-1-ene, cis-but-2-ene, trans-but-2-ene, 2-methylprop-1-ene, pent-1-ene, cis-pent-2-ene, trans-pent-2-ene, 2-methylbut-1-ene, 2-methylbut-2-ene and 3-methylbut-1-ene,

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 15 , 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 15 , 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 15 , wherein the alkene is a butene or a pentene.

19. The process of claim 15 , wherein the alkene is a pentene.

20. The process of claim 15 , wherein the composition comprises from 0.01% to 5% of alkene compound.

21. The process of claim 15 , wherein the composition comprises from 0.2% to 1% of alkene compound.

22. The process of claim 15 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 90%.

23. The process of claim 15 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 99%.

24. The process of claim 15 , wherein the 1-chloro-3,3,3-trifluoropropene is in trans form in a weight proportion greater than or equal to 99.9%.

25. The process of claim 15 , 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.

26. The process of claim 15 , wherein the composition is free of lubricant.

Assignments (2)
CHANGE OF ADDRESS Recorded Jul 4, 2025
From: ARKEMA FRANCE
To: ARKEMA FRANCE
Reel/Frame 071814/0739 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 24, 2018
From: RACHED, WISSAM; GUERIN, SOPHIE; KINDLER, PASCALE
To: ARKEMA FRANCE
Reel/Frame 044717/0101 →
Priority Claims (1)
FR 15 52222 · Mar 18, 2015 · national
Continuity (2)
Continuation 15073108 · Mar 17, 2016
Related Publication 20180148395A1 · May 31, 2018