US3173872A - Compositions of fluorocarbons - Google Patents
Compositions of fluorocarbons Download PDFInfo
- Publication number
- US3173872A US3173872A US179236A US17923662A US3173872A US 3173872 A US3173872 A US 3173872A US 179236 A US179236 A US 179236A US 17923662 A US17923662 A US 17923662A US 3173872 A US3173872 A US 3173872A
- Authority
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- United States
- Prior art keywords
- compositions
- boiling
- refrigerants
- refrigeration
- difluoromethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 44
- 238000009835 boiling Methods 0.000 claims description 32
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 18
- QYSGYZVSCZSLHT-UHFFFAOYSA-N octafluoropropane Chemical compound FC(F)(F)C(F)(F)C(F)(F)F QYSGYZVSCZSLHT-UHFFFAOYSA-N 0.000 claims description 11
- 229960004065 perflutren Drugs 0.000 claims description 11
- 239000003507 refrigerant Substances 0.000 description 18
- 238000005057 refrigeration Methods 0.000 description 14
- 239000007791 liquid phase Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- -1 difluoromethane-perfluoropropane Chemical compound 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011737 fluorine Chemical group 0.000 description 2
- 229910052731 fluorine Chemical group 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical class [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/04—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa
Definitions
- This invention relates to fluorinated hydrocarbons, and more particularly to constant boiling fluorocarbon mixtures which comprise difiuorornethane and pertluoropropane and which are especially adapted for use as high capacity, low temperature refrigeration compositions.
- the refrigeration capacity of a given amount of re frigerant is largely a function of boiling point, the lower boiling refrigerants generally offering the greater capacity at a given evaporator temperature. This factor to a great extent influences the design of refrigeration equipment and aifects capacity, power requirements, size and cost of the unit.
- Another important factor directly related to boiling point of the refrigerant is minimum cooling temperature obtained in the evaporator during the refrigeration cycle, the lower boiling refrigerants being used to achieve the lower refrigeration temperatures. For these reasons a large number of refrigerants of different boiling temperature and capacity are required to permit flexibility in design, and the art is continuously faced with the problem of providing new refrigerants as the need arises for new capacities and types of installations.
- the lower aliphatic hydrocarbons when substituted by chlorine and fluorine are well known to have potential as refrigerants. Many of these chlorofluorohydrocarbons exhibit certain desired properties including low cost, loW specific volume, low toxicity and chemical inertness which have resulted in the extensive use of such compounds in a large number of refrigeration applications. Examples of such compounds include difluorodichloromethane, B.P. 29.8 C., chlorodifiuoromethane, B.P. 40.8 C., fiuorodichloromethane, BI. 89 C., fluorotrichloromethane, B1. 23.8" C., and tetrafluorodichloroethane, 13.1. 3.5 C.
- a compound having considerable potential as a low temperature refrigerant is difiuoromethane, B.P. l.6 C.
- This fluorocarbon possesses many of the desired properties for use in refrigeration notwithstanding the presence of 2 hydrogen atoms which tend to induce flammability which may be objectionable in some refrigeration applications. While fiuorocarbons of this type are low boiling, the limited number of such compounds having the desired refrigerant properties represent widely different boiling points and fail to provide a satisfactory ran e of low boiling refrigerants of different capacity.
- An object of the present invention is to provide new low temperature compositions especially suitable for use as refrigerants. More particularly, it is an object to provide new refrigerants boiling lower and having greater capacity than the low boiling difluoromethane. Another object is to provide new low boiling compositions composed of difiuoromethane mixtures which are useful in producing refrigeration in those systems in which cooling is achieved by evaporation in the vicinity of the body to be cooled. A further object is to provide low boiling difluoromethane compositions in which the flammability is reduced to substantially negligible proportions.
- compositions consisting of difiuoromethane and approximately 10 mole percent to 62 mol percent perfluoropropane form a mixture system of liquid compositions which have a boiling temperature of about -58.1 C.
- These difluoromethaneperfiuoropropane compositions with the -58.l C. boiling temperature represent a marked reduction as compared with the boiling temperature of the lower boiling difiuoromethane component.
- the indicated difluoromethane-perfluoropropane compositions provide substantially increased refrigeration capacity and represent new refrigerant compositions useful in obtaining high capacity low temperature refrigeration. Further, flammability of difluoromethane is reduced by admixture with perfiuoropropane such that all compositions within the indicated range are substantially non-flammable.
- Boiling points of difluoromethane-perfiuoropropane mixtures were determined experimentally using difluoromethane and perfiuoropropane each better than 99.9% pure.
- Difluoromethane-perfluoropropane mixtures of known composition were prepared and boiling points were measured in a vacuum jacketed boiling point tube under Dry Ice-acetone reflux. Temperatures were measured using a platinum resistance thermometer, and all determinations run in duplicate. The experimentally determined boiling points were corrected to a normal atmospheric pressure of 760 mm. of Hg and are sum marized below:
- compositions consisting of difluoromethane and about 10 mol percent to 62 mol percent perfluoropropane have the same boiling tempera ture of about -5 8.1 C.
- difluoromethane and perfluoropropane make-up of the compo sitions of the invention requires no special procedures.
- the difluoromethane and perfluoropropane employed should be substantially pure, preferably at least about 9910 percent pure, and contain no substances deleteriously affecting the boiling characteristics of the mixture compositions or use as refrigerants.
- the minimum boiling two-liquid phase mixture system termed between difiuorornethane and perfluoropropane provides a broad range of mixture compositions which boil at substantially constant temperature and give a con- 7 of difiuoromethane and perfiuoropropane, in which the stant vapor composition.
- These two-liquid phase mixtures differ from refrigerant mixtures proposed in the past which otfer only' a relatively narrow range of useful compositions. Whileprior mixtures boil generally only about 1-3? C. below the lower boiling component, the "mixture system "of the present invention results in a relatively large reduction of about'6.5 C. over the boiling point of difiuoromethane.
- compositions of the invention may be used in design of refrigeration equipment or reduced size operating at the evaporator tem- "peratures of about minus 15 and below. to e.g.' minus
- the compositions of the'invention exhibit desired refrigeration properties including low toxicity, chemical inertness, and substantial non-flammability.
- providing high camol percent of perfluoropropane is within the range of about l062.
- the process of producing refrigeration comprises condensing a mixture consisting of difiuoromethane and perfiuoropropane in which the mol percent of per fluoropropane is within the range of about 10 62, and thereafter evaporating said mixture in the vicinityof a body to be cooled. 7
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent Ollice 3,173,372 Patented Mar. 16, 1965 3,173,872 COMPOIT10NS F FLUORGCARBGNS Robert D. Broadiey, Hanover Township, Morris County,
NJ, and Lyman F. Kells, New York, N.Y., assignors to Allied Chemical Corporation, New York, N.Y., a
corporation of New York No Drawing. Filed Mar. 12, 1962, Ser. No. 17?,236
2 Claims. (Cl. 252-67) This invention relates to fluorinated hydrocarbons, and more particularly to constant boiling fluorocarbon mixtures which comprise difiuorornethane and pertluoropropane and which are especially adapted for use as high capacity, low temperature refrigeration compositions.
The refrigeration capacity of a given amount of re frigerant is largely a function of boiling point, the lower boiling refrigerants generally offering the greater capacity at a given evaporator temperature. This factor to a great extent influences the design of refrigeration equipment and aifects capacity, power requirements, size and cost of the unit. Another important factor directly related to boiling point of the refrigerant is minimum cooling temperature obtained in the evaporator during the refrigeration cycle, the lower boiling refrigerants being used to achieve the lower refrigeration temperatures. For these reasons a large number of refrigerants of different boiling temperature and capacity are required to permit flexibility in design, and the art is continuously faced with the problem of providing new refrigerants as the need arises for new capacities and types of installations.
The lower aliphatic hydrocarbons when substituted by chlorine and fluorine are well known to have potential as refrigerants. Many of these chlorofluorohydrocarbons exhibit certain desired properties including low cost, loW specific volume, low toxicity and chemical inertness which have resulted in the extensive use of such compounds in a large number of refrigeration applications. Examples of such compounds include difluorodichloromethane, B.P. 29.8 C., chlorodifiuoromethane, B.P. 40.8 C., fiuorodichloromethane, BI. 89 C., fluorotrichloromethane, B1. 23.8" C., and tetrafluorodichloroethane, 13.1. 3.5 C. While these chlorine-fluorine derivatives provide an adequate range of refrigerants for many purposes, only a very few boil sufficiently low to ofier any potential as low temperature refrigerants. A major reason for this is the presence of the heavier chlorine substituent which generally results in a higher boiling compound than those containing predominantly fluorine or hydrogen.
A compound having considerable potential as a low temperature refrigerant is difiuoromethane, B.P. l.6 C. This fluorocarbon possesses many of the desired properties for use in refrigeration notwithstanding the presence of 2 hydrogen atoms which tend to induce flammability which may be objectionable in some refrigeration applications. While fiuorocarbons of this type are low boiling, the limited number of such compounds having the desired refrigerant properties represent widely different boiling points and fail to provide a satisfactory ran e of low boiling refrigerants of different capacity.
Increased activity in the field of cryogenics and low temperature refrigeration gives rise to a need for new low temperature refrigerants representing different capacities than now available. An object of the present invention is to provide new low temperature compositions especially suitable for use as refrigerants. More particularly, it is an object to provide new refrigerants boiling lower and having greater capacity than the low boiling difluoromethane. Another object is to provide new low boiling compositions composed of difiuoromethane mixtures which are useful in producing refrigeration in those systems in which cooling is achieved by evaporation in the vicinity of the body to be cooled. A further object is to provide low boiling difluoromethane compositions in which the flammability is reduced to substantially negligible proportions.
In accordance with the invention it has been discovered that compositions consisting of difiuoromethane and approximately 10 mole percent to 62 mol percent perfluoropropane (C F B.P. 37.0 C. form a mixture system of liquid compositions which have a boiling temperature of about -58.1 C. These difluoromethaneperfiuoropropane compositions with the -58.l C. boiling temperature represent a marked reduction as compared with the boiling temperature of the lower boiling difiuoromethane component. The indicated difluoromethane-perfluoropropane compositions provide substantially increased refrigeration capacity and represent new refrigerant compositions useful in obtaining high capacity low temperature refrigeration. Further, flammability of difluoromethane is reduced by admixture with perfiuoropropane such that all compositions within the indicated range are substantially non-flammable.
Boiling points of difluoromethane-perfiuoropropane mixtures were determined experimentally using difluoromethane and perfiuoropropane each better than 99.9% pure. Difluoromethane-perfluoropropane mixtures of known composition were prepared and boiling points were measured in a vacuum jacketed boiling point tube under Dry Ice-acetone reflux. Temperatures were measured using a platinum resistance thermometer, and all determinations run in duplicate. The experimentally determined boiling points were corrected to a normal atmospheric pressure of 760 mm. of Hg and are sum marized below:
TABLE I Normal boiling points of CH F C 5 mixture system M01 percent C F Normal boiling in solution: point, C.
The data demonstrate that compositions consisting of difluoromethane and about 10 mol percent to 62 mol percent perfluoropropane have the same boiling tempera ture of about -5 8.1 C. The presence of a broad range of compositions havinng the same boiling temperature of 58.1 0., representing a relatively marked depression of about 65 C. over that of the low boiling difiuoromethane component, indicated the difiuoromethane and periluoropropane were only partially miscible within the indicated range and formed compositions having two liquid phases. Examination of the 9.9 mol percent and 61.7 mol percent perfluoropropane compositions showed the presence of two liquid phases and confirmed the formation of a two-liquid phase system, while examination of the 1.7 mol percent perfluoropropane composition showed only a single liquid phase. We find that when the two liquid phases are present, the entire range of compositions consisting of difluoromethane and approximately 10 to 62 mol percent perfiuoropropane will boil at a substantially constant temperature and give a constant vapor composition for the two-liquid phase compositions described.
Apart from use of the indicated amounts of difluoromethane and perfluoropropane make-up of the compo sitions of the invention requires no special procedures. The difluoromethane and perfluoropropane employed should be substantially pure, preferably at least about 9910 percent pure, and contain no substances deleteriously affecting the boiling characteristics of the mixture compositions or use as refrigerants. V
The minimum boiling two-liquid phase mixture system termed between difiuorornethane and perfluoropropane provides a broad range of mixture compositions which boil at substantially constant temperature and give a con- 7 of difiuoromethane and perfiuoropropane, in which the stant vapor composition. These two-liquid phase mixtures differ from refrigerant mixtures proposed in the past which otfer only' a relatively narrow range of useful compositions. Whileprior mixtures boil generally only about 1-3? C. below the lower boiling component, the "mixture system "of the present invention results in a relatively large reduction of about'6.5 C. over the boiling point of difiuoromethane. The compositions of the invention may be used in design of refrigeration equipment or reduced size operating at the evaporator tem- "peratures of about minus 15 and below. to e.g.' minus The compositions of the'invention exhibit desired refrigeration properties including low toxicity, chemical inertness, and substantial non-flammability. In addition to being useful as new refrigerants providing high camol percent of perfluoropropane is within the range of about l062. I
' 2; The process of producing refrigerationwhich comprises condensing a mixture consisting of difiuoromethane and perfiuoropropane in which the mol percent of per fluoropropane is within the range of about 10 62, and thereafter evaporating said mixture in the vicinityof a body to be cooled. 7
References @ited in the file of this patent 'UNITED STATES PATENTS 1,968,050 Midgley et al. July 31,1934 2,494,064 Simons et al Jan. 10, 1950 2,687,441 Price et al. Aug. 24, 1954 3,018,306 Sweeney et al. Jan. 23, 1962
Claims (1)
1. A LOW BOILING COMPOSITION CONSISTING OF A MIXTURE OF DIFLUOROMETHANE AND PERFLUOROPROPANE, IN WHICH THE MOLE PERCENT OF PERFLUOROPROPANE IS WITHIN THE RANGE OF ABOUT 10-62.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US179236A US3173872A (en) | 1962-03-12 | 1962-03-12 | Compositions of fluorocarbons |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US179236A US3173872A (en) | 1962-03-12 | 1962-03-12 | Compositions of fluorocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3173872A true US3173872A (en) | 1965-03-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US179236A Expired - Lifetime US3173872A (en) | 1962-03-12 | 1962-03-12 | Compositions of fluorocarbons |
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418242A (en) * | 1965-05-18 | 1968-12-24 | Du Pont | Refrigerant composition |
| US3444085A (en) * | 1966-07-28 | 1969-05-13 | Du Pont | Azeotropic composition |
| US3753345A (en) * | 1971-11-01 | 1973-08-21 | Aerojet General Co | Power fluid |
| EP0143509A1 (en) * | 1983-08-10 | 1985-06-05 | Imperial Chemical Industries Plc | Heat pumps |
| EP0430171A1 (en) * | 1989-11-30 | 1991-06-05 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| EP0430169A1 (en) * | 1989-11-30 | 1991-06-05 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| EP0430170A1 (en) * | 1989-11-30 | 1991-06-05 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| US5232618A (en) * | 1991-09-30 | 1993-08-03 | E. I. Du Pont De Nemours And Company | Substantially constant boiling compositions of difluoromethane and trifluoroethane or perfluoroethane |
| US5234613A (en) * | 1991-09-30 | 1993-08-10 | E.I. Du Pont De Nemours And Company | Substantially constant boiling compositions of difluoromethane and propane |
| US5248433A (en) * | 1992-04-30 | 1993-09-28 | E. I. Du Pont De Nemours And Company | Binary azeotropic mixtures of octafluoropropane and fluoroethane |
| US5304319A (en) * | 1989-11-30 | 1994-04-19 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| US5370811A (en) * | 1989-11-30 | 1994-12-06 | Matsushita Electric Industrial Co., Ltd. | Working fluid containing tetrafluoroethane |
| US5433879A (en) * | 1989-11-30 | 1995-07-18 | Matsushita Electric Industrial Co., Ltd. | Working fluid containing difluoroethane |
| US5645754A (en) * | 1993-03-02 | 1997-07-08 | E. I. Du Pont De Nemours And Company | Compositions including a hexafluoroprpoane and dimethyl ether for heat transfer |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1968050A (en) * | 1931-11-19 | 1934-07-31 | Gen Motors Corp | Heat transfer and refrigeration |
| US2494064A (en) * | 1947-03-31 | 1950-01-10 | Minnesota Mining & Mfg | Thermal hydrogenolysis of fluorocarbons to produce fluorocarbon hydrides |
| US2687441A (en) * | 1952-02-08 | 1954-08-24 | Du Pont | Preparation of fluorinated organic compounds |
| US3018306A (en) * | 1959-06-09 | 1962-01-23 | Allied Chem | Production of butyryl halides |
-
1962
- 1962-03-12 US US179236A patent/US3173872A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1968050A (en) * | 1931-11-19 | 1934-07-31 | Gen Motors Corp | Heat transfer and refrigeration |
| US2494064A (en) * | 1947-03-31 | 1950-01-10 | Minnesota Mining & Mfg | Thermal hydrogenolysis of fluorocarbons to produce fluorocarbon hydrides |
| US2687441A (en) * | 1952-02-08 | 1954-08-24 | Du Pont | Preparation of fluorinated organic compounds |
| US3018306A (en) * | 1959-06-09 | 1962-01-23 | Allied Chem | Production of butyryl halides |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3418242A (en) * | 1965-05-18 | 1968-12-24 | Du Pont | Refrigerant composition |
| US3444085A (en) * | 1966-07-28 | 1969-05-13 | Du Pont | Azeotropic composition |
| US3753345A (en) * | 1971-11-01 | 1973-08-21 | Aerojet General Co | Power fluid |
| EP0143509A1 (en) * | 1983-08-10 | 1985-06-05 | Imperial Chemical Industries Plc | Heat pumps |
| US5433879A (en) * | 1989-11-30 | 1995-07-18 | Matsushita Electric Industrial Co., Ltd. | Working fluid containing difluoroethane |
| EP0430169A1 (en) * | 1989-11-30 | 1991-06-05 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| EP0430170A1 (en) * | 1989-11-30 | 1991-06-05 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| US5304319A (en) * | 1989-11-30 | 1994-04-19 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| US5370811A (en) * | 1989-11-30 | 1994-12-06 | Matsushita Electric Industrial Co., Ltd. | Working fluid containing tetrafluoroethane |
| EP0430171A1 (en) * | 1989-11-30 | 1991-06-05 | Matsushita Electric Industrial Co., Ltd. | Working fluid |
| US5438849A (en) * | 1989-11-30 | 1995-08-08 | Matsushita Electric Industrial Co., Ltd. | Air conditioner and heat pump with tetra fluoroethane-containing working fluid |
| US5232618A (en) * | 1991-09-30 | 1993-08-03 | E. I. Du Pont De Nemours And Company | Substantially constant boiling compositions of difluoromethane and trifluoroethane or perfluoroethane |
| US5234613A (en) * | 1991-09-30 | 1993-08-10 | E.I. Du Pont De Nemours And Company | Substantially constant boiling compositions of difluoromethane and propane |
| US5788877A (en) * | 1991-09-30 | 1998-08-04 | E. I. Du Pont De Nemours And Company | Substantially constant boiling compositions of difluoromethane and trifluoroethane |
| US5248433A (en) * | 1992-04-30 | 1993-09-28 | E. I. Du Pont De Nemours And Company | Binary azeotropic mixtures of octafluoropropane and fluoroethane |
| US5645754A (en) * | 1993-03-02 | 1997-07-08 | E. I. Du Pont De Nemours And Company | Compositions including a hexafluoroprpoane and dimethyl ether for heat transfer |
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