IP Library Granted Patent US 9,085,721
Granted Patent B2
US 9,085,721 · App. 13/981,095 · Granted Jul 21, 2015

Azeotropic and azeotrope-like compositions involving certain haloolefins and uses thereof

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Quick Facts
Patent No.
US 9,085,721
App. No.
13/981,095
Granted
Jul 21, 2015
Kind
B2
Abstract

Azeotropic or azeotrope-like compositions are disclosed. The azeotropic or azeotrope-like compositions are mixtures of (A) a compound of the formula CF 3 CX═CHR a where X is H or F and R a is CF 3 CF 2 , CF 3 or Cl, provided that (i) when X is F, R a is Cl, (ii) when R a is CF 3 CF 2 or Cl, the compound of formula CF 3 CX═CHR a is the E configurational isomer, and (iii) when R a is CF 3 , the compound of formula CF 3 CX═CHR a is the Z configurational isomer; and (B) a compound of the formula CF 3 R b where R b is CHFCH 2 F or CH═CHCF 3 , provided that when R b is CH═CHCF 3 , X is F and the compound of formula CF 3 R b is the Z configurational isomer. Also disclosed are processes for using such azeotropic or azeotrope-like compositions for preparing a thermoplastic or thermoset foam, for producing refrigeration, for producing an aerosol product and for extinguishing and suppressing a fire; and as blowing agents, solvents, heat transfer media and dielectrics.

Claims (25)

1. A composition consisting essentially of:

(a) E-1,1,1,4,4,5,5,5-octafluoro-2-pentene; and

(b) 1,1,1,2,3-pentafluoropropane; wherein the 1,1,1,2,3-pentafluoropropane is present in an effective amount to form an azeotropic combination with the E-1,1,1,4,4,5,5,5-octafluoro-2-pentene.

2. The composition of claim 1 , consisting essentially of from about 3.9 mole % to about 24.1 mole % of E-1,1,1,4,4,5,5,5-octafluoro-2-pentene and from about 75.9 mole % to about 96.1 mole percent 1,1,1,2,3-pentafluoropropane.

3. The composition of claim 1 , consisting essentially of from about 3.9 mole % to about 24.1 mole % of E-1,1,1,4,4,5,5,5-octafluoro-2-pentene and from about 75.9 mole % to about 96.1 mole percent 1,1,1,2,3-pentafluoropropane, wherein the vapor pressure is from about 0.59 psia to about 346 psia at a temperature of from about −40° C. to about 140° C.

4. A composition consisting essentially of:

(a) E-1,1,1,4,4,5,5,5-octafluoro-2-pentene; and

(b) 1,1,1,2,3-pentafluoropropane; wherein the 1,1,1,2,3-pentafluoropropane is present in an effective amount to form an azeotrope-like combination with the E-1,1,1,4,4,5,5,5-octafluoro-2-pentene.

5. The composition of claim 4 , consisting essentially of from about 1 mole % to about 99 mole % of E-1,1,1,4,4,5,5,5-octafluoro-2-pentene and from about 99 mole % to about 1 mole % 1,1,1,2,3-pentafluoropropane.

6. The composition of claim 4 , consisting essentially of from about 1 mole % to about 99 mole % of to about 99 mole % of E-1,1,1,4,4,5,5,5-octafluoro-2-pentene and from about 99 mole % to about 1 mole % 1,1,1,2,3-pentafluoropropane, at a temperature of from about −40° C. to about 120° C.

7. A composition consisting essentially of:

(a) E-1-chloro-2,3,3,3-tetrafluoropropene; and

(b) 1,1,1,2,3-pentafluoropropane; wherein the 1,1,1,2,3-pentafluoropropane is present in an effective amount to form an azeotropic combination with the E-1-chloro-2,3,3,3-tetrafluoropropene.

8. The composition of claim 7 , consisting essentially of from about 65.6 mole % to about 86.7 mole % of E-1-chloro-2,3,3,3-tetrafluoropropene, and from about 13.3 mole % to about 34.4 mole % 1,1,1,2,3-pentafluoropropane.

9. The composition of claim 7 , consisting essentially of from about 65.6 mole % to about 86.7 mole % of E-1-chloro-2,3,3,3-tetrafluoropropene, and from about 13.3 mole % to about 34.4 mole % 1,1,1,2,3-pentafluoropropane, wherein the vapor pressure is from about 0.98 psia to about 333 psia at a temperature of from about −40° C. to about 130° C.

10. A composition consisting essentially of:

(a) E-1-chloro-2,3,3,3-tetrafluoropropene; and

(b) 1,1,1,2,3-pentafluoropropane; wherein the 1,1,1,2,3-pentafluoropropane is present in an effective amount to form an azeotrope-like combination with the E-1-chloro-2,3,3,3-tetrafluoropropene.

11. The composition of claim 10 , consisting essentially of from about 1 mole % to about 99 mole % of E-1-chloro-2,3,3,3-tetrafluoropropene and from about 99 mole % to about 1 mole % of 1,1,1,2,3-pentafluoropropane.

12. The composition of claim 10 , consisting essentially of from about 1 mole % to about 99 mole % of E-1-chloro-2,3,3,3-tetrafluoropropene and from about 99 mole % to about 1 mole % of 1,1,1,2,3-pentafluoropropane, at a temperature of from about −40° C. to about 120° C.

13. A composition consisting essentially of:

(a) Z-1,1,1,4,4,4-hexafluoro-2-butene; and

(b) E-1-chloro-2,3,3,3-tetrafluoropropene; wherein the E-1-chloro-2,3,3,3-tetrafluoropropene is present in an effective amount to form an azeotrope-like combination with the Z-1,1,1,4,4,4-hexafluoro-2-butene.

14. The composition of claim 13 , consisting essentially of from about 1 mole % to about 99 mole % of Z-1,1,1,4,4,4-hexafluoro-2-butene and from about 99 mole % to 1 mole % of E-1-chloro-2,3,3,3-tetrafluoropropene.

15. The composition of claim 13 , consisting essentially of from about 1 mole % to about 99 mole % of Z-1,1,1,4,4,4-hexafluoro-2-butene and from about 99 mole % to 1 mole % of E-1-chloro-2,3,3,3-tetrafluoropropene, at a temperature of from about −40° C. to about 140° C.

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 27, 2013
From: ROBIN, MARK L.
To: E. I. DU PONT DE NEMOURS AND COMPANY
Reel/Frame 030890/0224 →