IP Library Patent Application 16492188
Patent Application
App. No. 16/492,188

USES OF FLUORINATED EPOXIDES AND NOVEL MIXTURES THEREOF

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Patent No.
US None
App. No.
16/492,188
Abstract

This application relates to compositions comprising one or more partially fluorinated epoxides and/or one or more perfluorinated epoxides which may be useful in applications including refrigerants, air conditioning, heat transfer media, high-temperature heat pumps, organic Rankine cycles, fire extinguishing/fire suppression, propellants, foam blowing, solvents, dielectrics, and/or cleaning fluids.

Claims (79)

1 . A composition for use in refrigeration, in air conditioning, in heating, in heat transfer, in conversion of heat into mechanical work in a power cycle, as a foam blowing agent, as a solvent, or in preventing or quenching an electric discharge, comprising a refrigerant component, an air conditioning component, a heating component, a heat transfer component, a working fluid component, a blowing agent component, a solvent component, or a dielectric component, respectively, which is a compound of Formula (I):

wherein:

R 1 and R 4 are each independently H, Cl, F, Br, I, a partially fluorinated C 1-4 alkoxy, or a perfluorinated C 1-4 alkoxy; and

R 2 is selected from H, Cl, F, Br, I, a partially fluorinated C 1-10 alkyl, a perfluorinated C 1-10 alkyl, a partially fluorinated C 1-4 alkoxy, and a perfluorinated C 1-4 alkoxy;

wherein at least one of R 1 , R 2 , and R 4 is not H;

R 3 is selected from partially fluorinated C 1-10 alkyl and perfluorinated C 1-10 alkyl;

or alternatively, R 2 and R 3 are each independently selected from partially fluorinated or perfluorinated C 1-5 alkylene, which together form a monocyclic ring.

2 . The composition of claim 1 , wherein:

R 1 and R 4 are each independently H, Cl, F, a partially fluorinated C 1-4 alkoxy, or a perfluorinated C 1-4 alkoxy;

R 2 is H, F, partially fluorinated C 1-10 alkyl, or perfluorinated C 1-10 alkyl;

wherein at least one of R 1 , R 2 , and R 4 is not H; and

R 3 is selected from partially fluorinated C 1-10 alkyl and perfluorinated C 1-10 alkyl.

3 . The composition of claim 1 , wherein R 1 and R 4 are each independently H, Cl, or F; R 2 is F, CF 3 , CF 2 CF 3 , CF(CF 3 ) 2 , CF 2 CF 2 CF 3 , CF 2 CF 2 CF 2 CF 3 , or CF 2 CF 2 CF 2 CF 2 CF 3 ; and R 3 is CF 3 , CF 2 CF 3 , CF(CF 3 ) 2 , CF 2 CF 2 CF 3 , CF 2 CF 2 CF 2 CF 3 , or CF 2 CF 2 CF 2 CF 2 CF 3 .

4 . The composition of claim 1 , wherein R 1 and R 4 are each independently H, Cl, F, a partially fluorinated C 1-4 alkoxy, or a perfluorinated C 1-4 alkoxy; and R 2 and R 3 are each independently selected from partially fluorinated or perfluorinated C 1-5 alkylene, which together form a monocyclic ring.

5 . The composition of claim 1 , wherein R 1 and R 4 are H; R 2 is partially fluorinated or perfluorinated C 1-2 alkylene; and R 3 is partially fluorinated or perfluorinated C 1-2 alkylene; wherein said R 2 and R 3 are taken together form a 4-6 membered monocyclic ring.

6 . (canceled)

7 . The composition of claim 1 , wherein the compound of Formula (I) is selected from:

2,3-difluoro-2-(trifluoromethyl)oxirane;

2-fluoro-3-(trifluoromethyl)oxirane;

2,3-bis(trifluoromethyl)oxirane;

2-(trifluoromethyl)-3-(perfluoroethyl)oxirane;

2-(trifluoromethyl)-3-(perfluoropropan-2-yl)oxirane;

2,3-bis(perfluoropropyl)oxirane;

2-(perfluorobutyl)-3-(perfluoroethyl)oxirane;

2,3-bis(perfluorobutyl)oxirane;

2-(2,2,2-Trifluoroethoxy)-3-fluoro-2-(trifluoromethyl)-3-(perfluoroethyl)oxirane;

2,3-dichloro-2,3-bis(trifluoromethyl)oxirane;

2-fluoro-3-(perfluoropropan-2-yl)oxirane;

2,2,3,3,4,4-hexafluoro-6-oxa-bicyclo[3.1.0]hexane;

2,2,3,3-tetrafluoro-5-oxabicyclo[2.1.0]pentane;

2,3-difluoro-2-(perfluoroethyl)-3-(perfluoropropyl)oxirane; and

2,3-difluoro-2-(trifluoromethyl)-3-(perfluoropentyl)oxirane;

or a mixture thereof.

8 . (canceled)

9 . The composition of claim 1 , wherein the composition is a composition for use in refrigeration or air conditioning, wherein the composition comprises said refrigerant component or said air conditioning component, respectively.

10 - 12 . (canceled)

13 . A process for producing cooling, comprising evaporating the refrigerant component in the composition of claim 9 in the vicinity of a body to be cooled, and thereafter condensing said refrigerant component.

14 . A process for replacing an incumbent refrigerant, comprising substantially replacing said incumbent refrigerant with a composition of claim 9 .

15 - 18 . (canceled)

19 . A process for producing heating, comprising condensing the composition of claim 9 in the vicinity of a body to be heated, and thereafter evaporating said heating component.

20 . The composition of claim 1 , wherein the composition is for use in heat transfer, wherein the working fluid component is a heat transfer component.

21 . (canceled)

22 . The composition of claim 20 , wherein the composition further comprises difluoromethane, 1,1-difluoroethane, 1,1,1,2-tetrafluoroethane, pentafluoroethane, 1,1,1,2,3,3,3-heptafluoropropane, (E)-1,3,3,3-tetrafluoroprop-1-ene (E-HFO-1234ze), 2,3,3,3-tetrafluoroprop-1-ene (HFO-1234yf), (E)-1,1,1,4,4,4-hexafluorobut-2-ene (E-HFO-1336mzz), (Z)-1,1,1,4,4,4-hexafluorobut-2-ene (Z-1336mzz), (E)-1-chloro-3,3,3-trifluoropropene (E-1233zd), (Z)-1-chloro-3,3,3-trifluoropropene (Z-1233zd), (Z)-1-chloro-2,3,3,3-tetrafluoropropene (Z-HCFO-1224yd), (E)-1-chloro-2,3,3,3-tetrafluoropropene (E-HCFO-1224yd), (Z)-1,3,3,3-tetrafluoroprop-1-ene (Z-HFO-1234ze), (E)-1,2,3,3-tetrafluoropropene (E-HFO-1234ye), (Z)-1,2,3,3-tetrafluoropropene (Z-HFO-1234ye), (E)-1,1,1,4,4,5,5,5-octafluoro-2-pentene (E-HFO-1438mzz), (Z)-1,1,1,4,4,5,5,5-octafluoro-2-pentene (Z-HFO-1438mzz), (E)-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)but-1-ene (E-HFO-1438ezy), (Z)-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)but-1-ene (Z-HFO-1438ezy), 1,1,1,3,3-pentafluoropropane (HFC-245fa), 1-methoxyheptafluoropropane (HFE-7000),1,1,1,3,3-pentafluorobutane (HFC-365mfc), 1,1,1,2,2,3,4,5,5,5-decafluoropentane (HFC-4310mee), 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane (HFE-7100), methyl perfluoroheptene ether isomers, or (2E)-1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene (HFO-153-10mzzy), or a mixture thereof.

23 . (canceled)

24 . A process for transferring heat from heat source to heat sink, comprising transporting the composition of claim 20 from the heat source to the heat sink.

25 - 28 . (canceled)

29 . A process for converting heat into mechanical work in a power cycle, comprising the steps of heating the composition of claim 1 with a heat source to a temperature sufficient to pressurize the composition; and causing the pressurized composition to perform mechanical work.

30 - 35 . (canceled)

36 . A process of converting heat to mechanical work in a Rankine cycle comprising the steps of: (a) vaporizing the composition of claim 1 with a low temperature heat source; (b) expanding the resulting vapor through an expansion device to generate mechanical work; (c) cooling the resulting expanded vapor to condense the vapor into a liquid; (d) pumping the composition to said heat source to repeat the process.

37 - 40 . (canceled)

41 . A foamable composition for use in formation of a foam, comprising the foam blowing agent composition of claim 1 and one or more additional components capable of reacting and/or foaming under the proper conditions to form a foam or cellular structure.

42 . A process for forming a foam, comprising reacting or extruding the foamable composition of claim 41 under conditions effective to form a foam.

43 - 65 . (canceled)

66 . A process for dissolving a solute, comprising contacting and mixing said solute with a sufficient quantity of the composition according to claim 1 .

67 . A process of cleaning a surface, comprising contacting the composition of claim 62 with said surface.

68 . A process for removing at least a portion of water from the surface of a wetted substrate, comprising contacting the substrate with the composition of claim 1 and then removing the substrate from contact with the composition.

69 - 74 . (canceled)

75 . A composition for fire suppression or fire extinguishment, comprising (a) a fluoroepoxide selected from (Z)-2,3-difluoro-2-(trifluoromethyl)oxirane, (E)-2,3-difluoro-2-(trifluoromethyl)oxirane, trans-2-fluoro-3-(trifluoromethyl)oxirane, trans-2,3-bis(trifluoromethyl)oxirane, trans-2-(trifluoromethyl)-3-(perfluoroethyl)oxirane, cis-2-fluoro-3-(trifluoromethyl)oxirane, trans-2-fluoro-3-(perfluoropropan-2-yl)oxirane, or a mixture thereof; and (b) one or more of 2-bromo-1,1,1-trifluoro-2-propene, E-1,2-dichloro-1,2-difluoroethylene, Z-1,2-dichloro-1,2-difluoroethylene, E-1-chloro-3,3,3-trifluoropropene, Z-1-chloro-3,3,3-trifluoropropene, E-1,1,1,4,4,4-hexafluoro-2-butene, Z-1,1,1,4,4,4-hexafluoro-2-butene, perfluoroethyl perfluoroisopropyl ketone (F-ethyl isopropyl ketone), E-1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene), E-1,2,3,3,3-pentafluoropropene, Z-1,2,3,3,3-pentafluoropropene, E-1-chloro-2,3,3,3-tetrafluoropropene, Z-1-chloro-2,3,3,3-tetrafluoropropene, CF 3 I, carbon dioxide, nitrogen, and argon.

76 . (canceled)

77 . A process for extinguishing or suppressing a flame comprising dispensing the composition of claim 75 at said flame.

78 . (canceled)

79 . A method of reducing the flammability of a fluid comprising adding the composition of claim 75 to the fluid.

80 - 83 . (canceled)

84 . A sprayable composition comprising a propellant component and a co-propellant component comprising a compound of Formula (I):

wherein:

R 1 and R 4 are each independently H, Cl, F, Br, I, a partially fluorinated C 1-4 alkoxy, or a perfluorinated C 1-4 alkoxy; and

R 2 is selected from H, Cl, F, Br, I, a partially fluorinated C 1-10 alkyl, a perfluorinated C 1-10 alkyl, a partially fluorinated C 1-4 alkoxy, and a perfluorinated C 1-4 alkoxy;

wherein at least one of R 1 , R 2 , and R 4 is not H;

R 3 is selected from partially fluorinated C 1-10 alkyl and perfluorinated C 1-10 alkyl;

or alternatively, R 2 and R 3 are each independently selected from partially fluorinated or perfluorinated C 1-5 alkylene, which together form a monocyclic ring.

85 - 90 . (canceled)

91 . A method of anesthetizing a subject, comprising administering to the subject an effective amount of a compound of Formula (I):

wherein:

R 1 and R 4 are each independently H, Cl, F, Br, I, a partially fluorinated C 1-4 alkoxy, or a perfluorinated C 1-4 alkoxy; and

R 2 is selected from H, Cl, F, Br, I, a partially fluorinated C 1-10 alkyl, a perfluorinated C 1-10 alkyl, a partially fluorinated C 1-4 alkoxy, and a perfluorinated C 1-4 alkoxy;

wherein at least one of R 1 , R 2 , and R 4 is not H;

R 3 is selected from partially fluorinated C 1-10 alkyl and perfluorinated C 1-10 alkyl;

or alternatively, R 2 and R 3 are each independently selected from partially fluorinated or perfluorinated C 1-5 alkylene, which together form a monocyclic ring.

92 . (canceled)

Assignments (2)
PATENT SECURITY AGREEMENT Recorded May 7, 2020
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 052598/0572 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2019
From: PETROV, VIACHESLAV A.; BRANDT, DREW RICHARD; MINOR, BARBARA HAVILAND; KONTOMARIS, KONSTANTINOS; ROBIN, MARK L.; WYSONG, ERNEST BYRON; MUSYIMI, HARRISON K.; GLATT, CHRISTINE M.
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 050306/0349 →