WO2020132307A1 - Azeotrope or azeotrope-like compositions of 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) and applications thereof - Google Patents

Azeotrope or azeotrope-like compositions of 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) and applications thereof Download PDF

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Publication number
WO2020132307A1
WO2020132307A1 PCT/US2019/067587 US2019067587W WO2020132307A1 WO 2020132307 A1 WO2020132307 A1 WO 2020132307A1 US 2019067587 W US2019067587 W US 2019067587W WO 2020132307 A1 WO2020132307 A1 WO 2020132307A1
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WIPO (PCT)
Prior art keywords
azeotrope
composition
trifluoro
trifluoromethylcyclobutane
compositions
Prior art date
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Ceased
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PCT/US2019/067587
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English (en)
French (fr)
Inventor
Robert J. Stewart
Ryan J. Hulse
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Honeywell International Inc
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Honeywell International Inc
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Publication date
Application filed by Honeywell International Inc filed Critical Honeywell International Inc
Priority to JP2021535118A priority Critical patent/JP2022514029A/ja
Priority to EP19899850.2A priority patent/EP3898878A4/en
Priority to CN201980087444.4A priority patent/CN113272402B/zh
Priority to CA3124814A priority patent/CA3124814A1/en
Publication of WO2020132307A1 publication Critical patent/WO2020132307A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Definitions

  • the azeotrope or azeotrope-like composition may have a boiling point of about 46.48°C ⁇ 0.01 °C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • An“azeotrope” composition is a unique combination of two or more components.
  • An azeotrope composition can be characterized in various ways. For example, at a given pressure, an azeotrope composition boils at a constant characteristic temperature which is either greater than the higher boiling point component (maximum boiling azeotrope) or less than the lower boiling point component (minimum boiling azeotrope). At this characteristic temperature the same composition will exist in both the vapor and liquid phases. The azeotrope composition does not fractionate upon boiling or evaporation. Therefore, the components of the azeotrope composition cannot be separated during a phase change.
  • the present disclosure provides an azeotrope or azeotrope- 1 ike composition which comprises effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and trans- 1 ,2-dichloroethylene to form an azeotrope or azeotrope- 1 ike composition.
  • the term“effective amount” is an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope-like mixture.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 1 wt.%, about 10 wt.% or about 15 wt.%, or as great as about 40 wt.%, about 50 wt.% or about 70 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane, or within any range defined between any two of the foregoing values
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 30 wt.%, about 50 wt.% or about 60 wt.%, or as great as about 85 wt.%, about 90 wt.% or about 99 wt.% trans- 1 ,2-dichloroethylene, or within any range defined between any two of the foregoing values.
  • Boiling point temperature was measured using a comparative ebulliometer including two adjacent flasks fitted with individual, chilled reflux condensers.
  • the top, or reflux condenser, of each ebulliometer was cooled with a circulating, chilled fluid (50/50 water/propylene glycol) to attain a temperature of about 15°C, which is significantly lower than the normal boiling points of 67.8°C for 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and 48.5°C for trans- 1 ,2-dichloroethylene at a pressure of 14.7 psia.
  • each flask was equipped with a calibrated thermistor with an accuracy of ⁇ 0.01 °C.
  • One flask contained pure fluid (in this case, either frans-1 ,2-dichloroethylene or 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane), and was used as a control.
  • the other flask contained mixed fluid (in this case, a mixture of frans-1 ,2-dichloroethylene and 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane).
  • the comparative ebulliometer was used to measure the boiling point temperature of pure and mixed fluids at ambient pressure. Approximately 2-3 grams of a first fluid was charged into both the control and the measurement flasks and heated to reflux while stirring. When the temperature of the condensing fluid reached a constant value, the second fluid was added to the measurement flask in measured increments. Sufficient time delay was allowed between additions of the second fluid to achieve proper mixing of the two fluids and thermodynamic equilibration. The second fluid was not added to the control flask. Rather, the control flask was used to confirm constant pressure throughout the duration of the experiment by measuring an invariable boiling point for the pure first fluid.
  • composition versus boiling point data was obtained for the composition range from 1 to 70 weight percent of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and is presented below in Table 1 , which shows a minimum in temperature which indicates that an azeotrope had been formed, and this data is also presented in graphic form in Fig. 1.
  • the bubble point temperature of the mixture remained constant indicating that the mixture was azeotrope-like over a large composition range.
  • the present disclosure provides an azeotrope or azeotrope- 1 ike composition which comprises effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and n- pentane to form an azeotrope or azeotrope- 1 ike composition.
  • the term “effective amount” is an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope-like mixture.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, from about 3 wt.% to about 50 wt.% 1 , 2 , 2-trif I uoro- 1 - trifluoromethylcyclobutane, from about 8 wt.% to about 40 wt.% 1 ,2, 2-trif I uoro- 1- trifluoromethylcyclobutane, from about 13 wt.% to about 30 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane, or about 21 wt.% 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane, and from about 50 wt.% to about 97 wt.% n-pentane, from about 60 wt.% to about 92 wt.% n- pentane, from about 70 wt.% to about 87 w
  • the azeotrope or azeotrope-like composition of the present disclosure has a boiling point of about 35.39°C ⁇ 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the azeotrope or azeotrope-like composition may consist essentially of 1 , 2, 2-trifluoro-1 -trifluoromethylcyclobutane and n- pentane in the above amounts, or consist of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and n-pentane in the above amounts.
  • the azeotrope or azeotrope-like composition has a boiling point of about 35.39°C + 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 3 wt.%, about 8 wt.% or about 13 wt.%, or as great as about 30 wt.%, about 40 wt.% or about 50 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane, or within any range defined between any two of the foregoing values
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 50 wt.%, about 60 wt.% or about 70 wt.%, or as great as about 87 wt.%, about 92 wt.% or about 97 wt.% n-pentane, or within any range defined between any two of the foregoing values.
  • the azeotrope or azeotrope like composition comprises, consists essentially of, or consists of, about 21 wt.% and 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and about 79 wt.% of n-pentane.
  • the azeotrope or azeotrope-like composition of the present disclosure has a boiling point of about 35.39°C ⁇ 0.01 °C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the present disclosure also provides a composition comprising the azeotrope or azeotrope- 1 ike composition.
  • a composition comprising at least about 5 wt.% of the azeotrope or azeotrope-like composition, or at least about 15 wt.% of the azeotrope or azeotrope- 1 ike composition, or at least about 50 wt.% of the azeotrope or azeotrope-like composition, or at least about 70 wt.% of the azeotrope or azeotrope-like composition, or at least about 90 wt.% of the azeotrope or azeotrope-like composition.
  • Example 1 The comparative ebulliometer described in Example 1 was used to measure the boiling point temperature of pure and mixed fluids at ambient pressure. Approximately 2- 3 grams of a first fluid was charged into both the control and the measurement flasks and heated to reflux while stirring. When the temperature of the condensing fluid reached a constant value, the second fluid was added to the measurement flask in measured increments. Sufficient time delay was allowed between additions of the second fluid to achieve proper mixing of the two fluids and thermodynamic equilibration. The second fluid was not added to the control flask. Rather, the control flask was used to confirm constant pressure throughout the duration of the experiment by measuring an invariable boiling point for the pure first fluid.
  • the measurement was carried out by first introducing about 2 g of n-pentane having a purity of >99 area% as determined by gas chromatography (GC) into the ebulliometer by weighing the container before and after the addition using a balance having an accuracy of ⁇ 0.01 g. The liquid was brought to a boil and the equilibrium temperature of the n-pentane was recorded at the recorded barometric pressure. Then, 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane having a purity of > 99.9 area% as determined by gas
  • GC gas chromatography
  • composition versus boiling point data was obtained for the composition range from 0 to 70 weight percent of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and is presented below in Table 2, which shows a minimum in temperature which indicates that an azeotrope had been formed, and this data is also presented in graphic form in Fig. 2.
  • the bubble point temperature of the mixture remained constant indicating that the mixture was azeotrope-like over a large composition range.
  • TFMCB 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane
  • the azeotrope or azeotrope- 1 ike compositions may consist essentially of 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and ethanol, or the azeotrope or azeotrope- 1 ike compositions may consist of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol.
  • the present disclosure provides an azeotrope or azeotrope- 1 ike composition which comprises effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol to form an azeotrope or azeotrope-like composition.
  • the term “effective amount” is an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope-like mixture.
  • the present azeotrope or azeotrope- 1 ike compositions may consist essentially of combinations of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol, or consist of combinations of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol.
  • the present disclosure also provides a method of forming an azeotrope or azeotrope-like composition by mixing, combining, or blending, effective amounts of, 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and ethanol.
  • Any of a wide variety of methods known in the art for combining two or more components to form a composition can be used in the present methods.
  • 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol can be mixed, blended, or otherwise combined by hand and/or by machine, as part of a batch or continuous reaction and/or process, or via combinations of two or more such steps.
  • Both 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol are commercially available and can be procured from several different vendors.
  • the components can be provided in the required amounts, for example by weighing and then combining the amounts.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, from about 30 wt.% to about 98 wt.% 1 ,2,2-trifluoro-1 - trifluoromethylcyclobutane, from about 70 wt.% to about 96 wt.% 1 ,2,2-trifluoro-1 - trifluoromethylcyclobutane, from about 80 wt.% to about 90 wt.% 1 ,2,2-trifluoro-1 - trifluoromethylcyclobutane, or about 88 wt.% 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane, and from about 2 wt.% to about 70 wt.% ethanol, from about 4 wt.% to about 30 wt.% ethanol, from about 10 wt.% to about 20 wt.% ethanol, or about 12 wt.% ethanol.
  • the azeotrope or azeotrope-like composition of the present disclosure has a boiling point of about 66.61°C ⁇ 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the azeotrope or azeotrope- 1 ike composition may comprise from about 30 wt.% to about 98 wt.% 1 , 2, 2-trifluoro-1 -trifluoromethylcyclobutane and from about 70 wt.% to about 96 wt.% ethanol, or from about 80 wt.% to about 90 wt.% 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and from about 2 wt.% to about 70 wt.% ethanol, or from about 4 wt.% to about 30 wt.% 1 , 2, 2-trifluoro-1 -trifluoromethylcyclobutane and from about 10 wt.% to about 20 wt.% ethanol, or about 88 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane and about 12 wt.% ethanol.
  • the azeotrope or azeotrope-like composition may consist essentially of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol in the above amounts, or consist of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and ethanol in the above amounts.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 30 wt.%, about 70 wt.% or about 80 wt.%, or as great as about 90 wt.%, about 96 wt.% or about 98 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane, or within any range defined between any two of the foregoing values
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 2 wt.%, about 4 wt.% or about 10 wt.%, or as great as about 20 wt.%, about 30 wt.% or about 70 wt.% ethanol, or within any range defined between any two of the foregoing values.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little
  • composition comprises, consists essentially of, or consists of, about 88 wt.% and 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and about 12 wt.% of ethanol.
  • azeotrope or azeotrope-like composition of the present disclosure has a boiling point of about 66.61°C ⁇ 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the present disclosure also provides a composition comprising the azeotrope or azeotrope- 1 ike composition.
  • a composition comprising at least about 5 wt.% of the azeotrope or azeotrope-like composition, or at least about 15 wt.% of the azeotrope or azeotrope- 1 ike composition, or at least about 50 wt.% of the azeotrope or azeotrope-like composition, or at least about 70 wt.% of the azeotrope or azeotrope-like composition, or at least about 90 wt.% of the azeotrope or azeotrope-like composition.
  • Example 1 The comparative ebulliometer described in Example 1 was used to measure the boiling point temperature of pure and mixed fluids at ambient pressure. Approximately 2- 3 grams of a first fluid was charged into both the control and the measurement flasks and heated to reflux while stirring. When the temperature of the condensing fluid reached a constant value, the second fluid was added to the measurement flask in measured increments. Sufficient time delay was allowed between additions of the second fluid to achieve proper mixing of the two fluids and thermodynamic equilibration. The second fluid was not added to the control flask. Rather, the control flask was used to confirm constant pressure throughout the duration of the experiment by measuring an invariable boiling point for the pure first fluid.
  • the measurement was carried out by first introducing about 2 g of ethanol having a purity of >99 area% as determined by gas chromatography (GC) into the ebulliometer by weighing the container before and after the addition using a balance having an accuracy of ⁇ 0.01 g. The liquid was brought to a boil and the equilibrium temperature of the n-pentane was recorded at the recorded barometric pressure. Then, 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane having a purity of > 99.9 area% as determined by gas
  • TFMCB 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane
  • the azeotrope or azeotrope-like compositions may consist essentially of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and cyclopentane, or the azeotrope or azeotrope like compositions may consist of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and
  • the present disclosure provides an azeotrope or azeotrope- 1 ike composition which comprises effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and cyclopentane to form an azeotrope or azeotrope-like composition.
  • the term “effective amount” is an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope-like mixture.
  • the present azeotrope or azeotrope- 1 ike compositions may consist essentially of combinations of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and cyclopentane, or consist of combinations of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and cyclopentane.
  • the present disclosure also provides a method of forming an azeotrope or azeotrope-like composition by mixing, combining, or blending, effective amounts of, 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and cyclopentane.
  • Any of a wide variety of methods known in the art for combining two or more components to form a composition can be used in the present methods.
  • 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and cyclopentane can be mixed, blended, or otherwise combined by hand and/or by machine, as part of a batch or continuous reaction and/or process, or via combinations of two or more such steps.
  • Both 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and cyclopentane are commercially available and can be procured from several different vendors.
  • the components can be provided in the required amounts, for example by weighing and then combining the amounts.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, from about 20 wt.% to about 60 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane, from about 30 wt.% to about 50 wt.% 1 ,2,2-trifluoro-1 - trifluoromethylcyclobutane, from about 35 wt.% to about 40 wt.% 1 ,2,2-trifluoro-1 - trifluoromethylcyclobutane, or about 39 wt.% 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane, and from about 40 wt.% to about 80 wt.% cyclopentane, from about 50 wt.% to about 70 wt.% cyclopentane, from about 60 wt.% to about 65 wt.% cyclopentane, or about
  • the azeotrope or azeotrope- 1 ike composition of the present disclosure has a boiling point of about 45.59°C ⁇ 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the azeotrope or azeotrope- 1 ike composition may comprise from about 20 wt.% to about 60 wt.% 1 , 2, 2-trifluoro-1 -trifluoromethylcyclobutane and from about 40 wt.% to about 80 wt.% cyclopentane, or from about 30 wt.% to about 50 wt.% 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and from about 50 wt.% to about 70 wt.% cyclopentane, or from about 35 wt.% to about 40 wt.% 1 , 2 , 2-trif I uoro- 1 - trifluoromethylcyclobutane and from about 60 wt.% to about 65 wt.% cyclopentane, or about 39 wt.% 1 , 2, 2-trifluoro-1 -trifluoromethylcyclobutane and about 61
  • the azeotrope or azeotrope-like composition may consist essentially of 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane and cyclopentane in the above amounts, or consist of 1 ,2,2- trifluoro-1 -trifluoromethylcyclobutane and cyclopentane in the above amounts.
  • the azeotrope or azeotrope-like composition has a boiling point of about 45.59°C + 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 20 wt.%, about 30 wt.% or about 35 wt.%, or as great as about 40 wt.%, about 50 wt.% or about 60 wt.% 1 ,2,2-trifluoro-1- trifluoromethylcyclobutane, or within any range defined between any two of the foregoing values
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, as little as about 40 wt.%, about 50 wt.% or about 60 wt.%, or as great as about 65 wt.%, about 70 wt.% or about 80 wt.% cyclopentane, or within any range defined between any two of the foregoing values.
  • the azeotrope or azeotrope like composition comprises, consists essentially of, or consists of, about 39 wt.% and 1 ,2,2- trifluoro-1-trifluoromethylcyclobutane and about 61 wt.% of cyclopentane.
  • the azeotrope or azeotrope-like composition of the present disclosure has a boiling point of about 45.59 °C ⁇ 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the present disclosure also provides a composition comprising the azeotrope or azeotrope- 1 ike composition.
  • a composition comprising at least about 5 wt.% of the azeotrope or azeotrope-like composition, or at least about 15 wt.% of the azeotrope or azeotrope- 1 ike composition, or at least about 50 wt.% of the azeotrope or azeotrope-like composition, or at least about 70 wt.% of the azeotrope or azeotrope-like composition, or at least about 90 wt.% of the azeotrope or azeotrope-like composition.
  • the present disclosure provides an azeotrope or azeotrope- 1 ike composition which comprises effective amounts of 1 ,2, 2-trifluoro-1 -trifluoromethylcyclobutane and perfluoro(2-methyl-3-pentanone) to form an azeotrope or azeotrope-like composition.
  • the term“effective amount” is an amount of each component which, when combined with the other component, results in the formation of an azeotrope or azeotrope like mixture.
  • the azeotrope or azeotrope-like composition comprises, consists essentially of, or consists of, about 10 wt.% and 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and about 90 wt.% of perfluoro(2-methyl-3-pentanone).
  • the azeotrope or azeotrope-like composition of the present disclosure has a boiling point of about 48.70°C ⁇ 0.01°C at a pressure of about 14.7 psia ⁇ 0.2 psia.
  • the present disclosure also provides a composition comprising the azeotrope or azeotrope- 1 ike composition.
  • a composition comprising at least about 5 wt.% of the azeotrope or azeotrope-like composition, or at least about 15 wt.% of the azeotrope or azeotrope- 1 ike composition, or at least about 50 wt.% of the azeotrope or azeotrope-like composition, or at least about 70 wt.% of the azeotrope or azeotrope-like composition, or at least about 90 wt.% of the azeotrope or azeotrope-like composition.
  • the mechanical work may be transmitted to an electrical device such as a generator to produce electrical power.
  • an electrical device such as a generator to produce electrical power.
  • heat pumps examples include heat pump tumble driers, reversible heat pumps, and air-to-air heat pumps.
  • the heat pump may also be a heat pump water heater. It will be appreciated that the heat pump may be a high temperature heat pump.
  • “high temperature heat pump” it is meant a heat pump that is able to generate temperatures of at least about 80°C, preferably at least about 90°C, more preferably at least about 100°C.
  • the refrigerant or heat transfer compositions of the present invention may be used as secondary fluid in a secondary loop system.
  • a secondary loop system contains a primary vapor compression system loop that uses a primary refrigerant and whose evaporator cools the secondary loop fluid.
  • the secondary fluid then provides the necessary cooling for an application.
  • the secondary fluid must be non-flammable and have low-toxicity since the fluid in such a loop is potentially exposed to humans in the vicinity of the cooled space.
  • the refrigerant or heat transfer composition of the present invention may be used as a“secondary fluid” in a secondary loop system.
  • the primary fluid used in the primary loop may be selected from but not limited to HFO-1234ze(E), HFO-1234yf, propane, R455A, R32, R466A, R44B, R290, R717, R452B, R448A, and R449A, preferably HFO-1234ze(E), HFO-1234yf, or propane.
  • Examples of where secondary loop refrigeration systems may be used include a low temperature refrigeration system, a medium temperature refrigeration system, a commercial refrigerator, a commercial freezer, an industrial freezer, an industrial refrigerator and a chiller.
  • secondary loop air conditioning systems examples include in mobile air conditioning systems.
  • Mobile air-conditioning systems including air conditioning of road vehicles such as automobiles, trucks and buses, as well as air conditioning of boats, and trains.
  • the secondary loop air conditioning system may be a stationary air conditioning system.
  • stationary air conditioning systems include a chiller, particularly a positive displacement chiller, more particularly an air cooled or water cooled direct expansion chiller, which is either modular or conventionally singularly packaged, a residential air conditioning system, particularly a ducted split or a ductless split air conditioning system, a residential heat pump, a residential air to water heat pump/hydronic system, an industrial air conditioning system a commercial air conditioning system, particularly a packaged rooftop unit and a variable refrigerant flow (VRF) system; a commercial air source, water source or ground source heat pump system.
  • a chiller particularly a positive displacement chiller, more particularly an air cooled or water cooled direct expansion chiller, which is either modular or conventionally singularly packaged
  • a residential air conditioning system particularly a ducted split or a ductless split air conditioning system
  • a residential heat pump a residential air to water heat pump/hydronic system
  • an industrial air conditioning system a commercial air conditioning system, particularly a packaged rooftop unit and a variable refrigerant flow (VRF) system
  • the secondary loop air conditioning or refrigeration system may comprise a suction line/liquid line heat exchanger (SL-LL HX).
  • the heat transfer fluids, thermal management fluid, refrigerant or heat transfer compositions of the invention may be used as a for existing fluids.
  • the thermal management fluid of the invention may be used as a replacement for existing fluids such as HFC-4310mee, HFE-7100 and HFE-7200.
  • the replacement may be in existing systems, or in new systems.
  • Step (a) may involve removing at least about 5wt%, at least about 10wt%, at least about 15wt%, at least about 50wt% at least about 70wt%, at least about 90wt%, at least about 95wt%, at least about 99wt% or at least about 99.5wt% of said existing refrigerant from said system prior to step (b).
  • the method may optionally comprise the step of flushing said system with a solvent after conducting step (a) and prior to conducting step (b).
  • compositions are used as heat transfer fluids in the form of refrigerants or working fluids in electronic devices including personal computers, microprocessors, servers, cell phones, tablets, digital home appliances (e.g. televisions, media players, games consoles etc.), personal digital assistants, Datacenters, hybrid or electric vehicles, wind turbine, train engine, or generator, preferably wherein the electronic device is a hybrid or electric vehicle.
  • electronic devices including personal computers, microprocessors, servers, cell phones, tablets, digital home appliances (e.g. televisions, media players, games consoles etc.), personal digital assistants, Datacenters, hybrid or electric vehicles, wind turbine, train engine, or generator, preferably wherein the electronic device is a hybrid or electric vehicle.
  • the compositions demonstrate effective heat transfer properties.
  • perfluoro(2-methyl-3-pentanone) is prepared and demonstrates effective heat transfer properties in these applications.
  • compositions are used as heat transfer fluids in the form of refrigerants or working fluids in a process for converting thermal energy to mechanical energy in an Organic Rankine Cycle (ORC), the method comprising the steps of i) vaporizing a working fluid with a heat source and expanding the resulting vapor, then ii) cooling the working fluid with a heat sink to condense the vapor.
  • ORC Organic Rankine Cycle
  • perfluoro(2-methyl-3-pentanone) is prepared and demonstrates effective heat transfer properties in this application.
  • compositions are used as heat transfer fluids in the form of refrigerants or working fluids in a method of heating a fluid or body using a heat pump including the steps of (a) condensing a refrigerant in the vicinity of the fluid of body or be heated, and (b) evaporating said refrigerant.
  • the compositions demonstrate effective heat transfer properties.
  • an azeotrope or azeotrope-like composition consisting essentially of effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and
  • an azeotrope or azeotrope-like composition consisting essentially of effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and
  • polyisocyanurate foam and a phenolic foam may also used as a blowing agent for thermoplastic foams selected from a polyethylene foam, a polypropylene foam, a
  • Solvent compositions including the present azeotropic or azeotrope-like compositions are loaded into aerosol cans. Aerosol valves are crimped into place and HFC- 134a is added through the valves to achieve a pressure in the cans of about 20 PSIG. The compositions are then sprayed onto metal coupons soiled with solder flux. The flux is removed and the coupons are visually clean.
  • Example 14
  • Aspect 13 is the azeotrope or azeotrope-like composition of Aspect 12, consisting essentially of from about 8 wt.% to about 40 wt.% 1 , 2 , 2-trif I uo ro- 1 - trifluoromethylcyclobutane and from about 60 wt.% to about 92 wt.% n-pentane.
  • Aspect 36 is the method of Aspect 35, wherein the thermal management fluid is in direct contact with the heat generating component.
  • Aspect 37 is the method of Aspect 35 or Aspect 36, wherein the thermal management fluid consists essentially of an azeotrope or azeotrope-like composition consisting essentially of effective amounts of 1 ,2,2-trifluoro-1-trifluoromethylcyclobutane and perfluoro(2-methyl-3-pentanone).
  • Aspect 40 is the method of Aspect 39, wherein the electronic device is a hybrid or electric vehicle.

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EP19899850.2A EP3898878A4 (en) 2018-12-21 2019-12-19 Azeotrope or azeotrope-like compositions of 1,2,2-trifluoro-1-trifluoromethylcyclobutane (tfmcb) and applications thereof
CN201980087444.4A CN113272402B (zh) 2018-12-21 2019-12-19 1,2,2-三氟-1-三氟甲基环丁烷（tfmcb）的共沸物或类共沸物组合物及其应用
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