GB2546845A - Composition - Google Patents

Composition Download PDF

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Publication number
GB2546845A
GB2546845A GB1615045.0A GB201615045A GB2546845A GB 2546845 A GB2546845 A GB 2546845A GB 201615045 A GB201615045 A GB 201615045A GB 2546845 A GB2546845 A GB 2546845A
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Prior art keywords
mol
composition
azeotropic
column
bara
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GB201615045D0 (en
Inventor
Lloyd Gary
Mary Skae Clare
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Mexichem Fluor SA de CV
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Mexichem Fluor SA de CV
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Priority to GB1615045.0A priority Critical patent/GB2546845A/en
Publication of GB201615045D0 publication Critical patent/GB201615045D0/en
Publication of GB2546845A publication Critical patent/GB2546845A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/38—Separation; Purification; Stabilisation; Use of additives
    • C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
    • C07C17/386—Separation; Purification; Stabilisation; Use of additives by distillation with auxiliary compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An azeotropic or near-azeotropic composition comprising HF and CH2ClCHClCHF3 (243db). The composition preferably consists essentially of HF and 243db, or more preferably consists of HF and 243db. The use of the azeotropic or near-azeotropic composition in the manufacture of one or more hydrofluoroolefins, particularly CHFCHF3 (1234zeE) or CH2CHFCF3, is also claimed. A process for the separation of the claimed azeotrpic or near-azeotropic composition is provided. The separation process preferably performed using pressure swing distillation, particularly wherein the pressure swing apparatus comprises two columns operated sequentially at different pressures and/or at different temperatures. The first column is preferably operated at a pressure 0.5 to 15 bara and at a temperature of 1°C to 115°C. The second column is preferably operated a pressure between 1 to 20 bara and at a temperature of 18°C to 203°C. The separation process is preferably continuous.

Description

Composition
The present invention relates to azeotropic or near-azeotropic compositions comprising CH2CICHCICF3 (243db) and HF along with uses thereof of such compositions. 2,3-dichloro-1,1,1-trifluoropropane is also known as R243db, or more simply 243db. Hereinafter, unless otherwise stated, 2,3-dichloro-1,1,1-trifluoropropane will be referred to as 243db.
The listing or discussion of a prior-published document in this specification should not necessarily be taken as an acknowledgement that the document is part of the state of the art or is common general knowledge.
The present invention provides azeotropic or near-azeotropic compositions comprising 243db and HF.
Also provided by the invention is the use of such azeotropic or near-azeotropic compositions (e.g. as an intermediate) in the manufacture of one or more hydrofluoroolefins.
Further provided by the invention is the use of such azeotropic or near-azeotropic compositions (e.g., as an intermediate) in the manufacture of 2,3,3,3-tetrafluoropropene (1234yf) and/or 1,3,3,3-tetrafluoropropene (1234ze) and/or 2-chloro-3,3,3-trifluoropropene (1233xf).
Also provided is a process for the separation of an azeotropic or near-azeotropic composition of the invention.
Compositions of the Invention
In a first aspect, the invention provides an azeotropic or near-azeotropic composition comprising HF and CH2CICHCICF3 (243db).
In an embodiment, the azeotropic composition of the invention consists essentially of HF and 243db. In a further embodiment, the composition consists of HF and 243db.
By azeotrope or azeotropic composition, we mean a preferably binary composition which at vapour-liquid equilibrium has the same composition in both the liquid and vapour phase, and whose boiling point is lower than that of either of the pure components. By near-azeotrope or near-azeotropic composition (e.g. a near-azeotropic composition of 243db and HF), we mean a composition that behaves similarly to an azeotrope composition (i.e. the composition has constant boiling characteristics or a tendency not to fractionate upon boiling), but may not have all of the properties of an azeotrope, for example binary liquid compositions whose vapour pressure is above that of the pure component with the lower boiling point (e.g. HF compared to 243db) when measured at equivalent temperature, but whose equilibrium vapour composition may differ from the liquid composition.
In essence, at a given pressure, a boiling azeotrope or near azeotrope composition has substantially the same constituent proportions in the vapour phase as in the boiling liquid phase. This means that no (or substantially no) fractionation of the components in the liquid composition takes place.
Furthermore, it is also contemplated that the azeotropic or near-azeotropic composition of the invention is a heteroazeotropic composition, depending on the temperature and pressure of the system, where the yapour phase coexists with two liquid phases.
Preferably, the azeotropic or near-azeotropic composition of the invention comprises, or preferably consists of, about 10 mol% to about 99 mol% HF and from about 90 mol% to about 1 mol% 243db. Alternatively, the azeotropic or near-azeotropic composition of the invention comprises, or preferably consists of, from about 20 mol% to about 99 mol% HF and from about 80 mol% to about 1 mol% 243db, such as about 30 mol% to about 99 mol% HF and from about 70 mol% to about 1 mol% 243db, for example about 40 mol% to about 99 mol% HF and from about 60 mol% to about 1 mol% 243db, preferably about 50 mol% to about 99 mol% HF and from about 50 mol% to about 1 mol% 243db, such as from about 60 mol% to about 99 mol% HF and from about 40 mol% to about 1 mol% 243db, for example from about 70 mol% to about 99 mol% HF and from about 30 mol% to about 1 mol% 243db, preferably from about 80 mol% to about 99 mol% HF and from about 20 mol% to about 1 mol% 243db, such as from about 85 mol% to about 99 mol% HF and from about 15 mol% to about 1 mol% 243db, for example from about 90 mol% to about 99 mol% HF and from about 10 mol% to about 1 mol% 243db, such as from about 90 mol% to about 98 mol% HF and from about 10 mol% to about 2 mol% 243db and most preferably from about 92 mol% to about 98 mol% HF and from about 8 mol% to about 2 mol% 243db.
In an embodiment, the azeotropic or near-azeotropic composition of the invention is present at temperatures of from about -20°C to about +90°C, such as from about from about 0°C to about +70°C, preferably from temperatures of from about +30°C to about +70°C.
In a further embodiment, the azeotropic or near-azeotropic composition of the invention is present at pressures of from about 0.5 bara to about 30 bara, for example from about 1 to about 10 bara.
In a preferred embodiment, the azeotropic or near-azeotropic composition of the invention comprises from about 92 mol% to about 98 mol% HF and from about 10 mol% to about 3 mol% 243db, wherein the azeotropic or near-azeotropic composition is present at temperatures of between about -20°C to about +70°C and pressures of between about 1 bara to about 10 bara.
In some embodiments, the azeotropic or near-azeotropic composition comprises from about 20 mol% to about 98 mol% HF and from about 80 mol% to about 2 mol% 243db at temperatures of about -20°C to about 70°C and pressures of about 0.18 bara to about 5.6 bara. In further embodiments, the azeotropic or near-azeotropic composition comprises from about 30 mol% to about 98 mol% HF and from about 70 mol% to about 2 mol% 243db at temperatures of about 0°C to about 70°C and pressures of about 0.5 bara to about 5.6 bara. In further embodiments, the azeotropic or near-azeotropic composition comprises from about 30 mol% to about 98 mol% HF and from about 70 mol% to about 2 mol% 243db at temperatures of from about 30°C to about 70°C and pressures of about 1.4 bara to about 5.6 bara.
In another aspect, the invention provides the use of an azeotropic or near-azeotropic composition comprising CH2CICHCICF3 (243db) and HF (e.g. as an intermediate) in the manufacture of one or more hydrofluoroolefins. For example, the azeotropic or near-azeotropic composition of the invention has been found to be particularly useful in the manufacture of 1234yf and/or 1234ze and/or 2-chloro-3,3,3-trifluoropropene (1233xf).
In a further aspect, the invention provides a process for the separation of an azeotropic or near-azeotropic composition comprising CH2CICHCICF3 (243db) and HF comprising separating the composition via the use of a pressure swing apparatus. Such pressure swing apparatus set-ups may comprise at least two columns, which may be operated sequentially at different pressures. Similarly, the columns may be operated sequentially at two different temperatures.
In an embodiment, a first column A may be operated at a pressure of from about 0.5 to about 15 bara, such as from about 0.5 to about 5 bara, preferably from about 0.5 to about 2 bara, for example about 1 bara.
In a further embodiment, a second column B may be operated at a pressure of from about 1to about 20 bara, such as from about 5 to about 20 bara, preferably from about 15 to about 20 bara, for example about 20 bara.
In another embodiment, column A is operated at a temperature of from about 1°C to about 115°C, such as from about 1°C to about 80°C, preferably from about 15°C to about 80°C. In one embodiment, a temperature gradient exists in column A where the temperature varies from 18 °C at one end of the column to 76°C at the other end.
In another embodiment, column B is operated at a temperature of from about 18°C to about 203°C, such as from about 67°C to about 203°C, preferably from about 109°C to about 203°C. Advantageously, a temperature gradient exists in column B where the temperature varies from 121 °C at one end of the column to 129°C at the other end.
In an embodiment, an azeotropic or near-azeotropic feed composition (Fi) of the invention comprising 243db and HF is fed into column A. Such compositions may comprise, or preferably consist of, about 50 mol% to about 97 mol% HF and from about 50 mol% to about 3 mol% 243db, advantageously from about 60 mol% to about 97 mol% HF and from about 40 mol% to about 3 mol% 243db, such as about 70 mol% to about 97 mol% HF and from about 30 mol% to about 3 mol% 243db, for example about 80 mol% to about 97 mol% HF and from about 20 mol% to about 3 mol% 243db, preferably about 90 mol% to about 97 mol% HF and from about 10 mol% to about 3 mol% 243db. Advantageously, the Fi composition consists of about 97 mol% HF and about 3 mol% 243db.
On entering column A, 243db is separated from the Fi composition. As such, 243db may be recovered from column A yielding a 243db rich composition (Di) comprising greater than about 90 mol% 243db, such as greater than about 95 mol% 243db, preferably greater than 99 mol% 243db, and an azeotropic or near-azeotropic composition (Ci) comprising 243db and HF in a molar ratio that is richer in HF than Fi. Preferably, composition Di is recovered from column A at the higher temperature region of the column.
On recovering the composition Di from column, a preferably azeotropic or near-azeotropic composition Ci comprising 243db and HF is fed into column B, wherein the Ci composition is separated into two further fluid compositions, wherein HF is separated from the azeotrope composition to yield a composition (D2) comprising greater than about 90 mol% HF, such as greater than about 95 mol% HF, preferably greater than 99 mol% HF, and an azeotropic or near-azeotropic composition (C2) comprising 243db and HF in a molar ratio that is richer in 243db than C1. Preferably, composition D2 is recovered from column B at the higher temperature region of the column.
The recovery of compositions D1 and C1 from column A may occur simultaneously or sequentially. Preferably, the recovery of compositions D1 and C1 occurs simultaneously.
On recovering the composition D2 from column B, a preferably azeotropic or near-azeotropic composition (C2) consisting of 243db and HF may be recovered at the opposite end of the column. As HF has been recovered from composition C1, the C2 composition is richer in 243db than C1. Preferably, such compositions comprise, or preferably consist of, about 3 mol% to about 10 mol% 243db and from about 90 mol% to about 97 mol% HF, such as from about 4 mol% to about 10 mol% 243db and from 90 mol% to about 96 mol% HF. Preferably, such compositions comprise, or preferably consist of, 10 mol% 243db and 90 mol% HF.
The recovery of compositions D2 and C2 from column B may occur simultaneously or sequentially. Preferably, the recovery of compositions D2 and C2 occurs simultaneously.
In an embodiment, upon recovery of the composition C2from column B, this composition may be recycled back into column A. Preferably, this process is, therefore, continuous.
Although it is preferred that the separation of composition F1 is via first entering column A then column B, it is envisaged that the process may be reversed and the azeotropic or near-azeotropic composition may be subjected to the separation process in column B first before being subjected to the separation process in column A.
Embodiments of the present invention will now be described with reference to the following drawings:
Figure 1 shows a pressure swing apparatus set-up, which is suitable for the separation of azeotropic or near-azeotropic compositions of the invention.
Figure 2 shows the results obtained when measuring the vapour mole fraction of 243db and liquid mole fraction of 243db using varying compositions of 243db and HF at pressures of 1 bar to 10 bar.
Figures 3 to 6 show the results obtained when measuring the vapour pressure of varying compositions of 243db and HF at temperatures of -20°C, 0°C, 30°C and 70°C.
The present invention provides an azeotropic or near-azeotropic composition comprising HF and 243db. Without wishing to be bound by theory, the existence of an azeotropic or near-azeotropic composition is generally dependent on temperature, pressure and the ratio of components in the composition. By varying the temperature, pressure and composition, an azeotrope or near-azeotropic composition of the invention may occur at any point between these values.
The components of azeotropic or near-azeotropic compositions may be separated via the use of a pressure swing distillation apparatus. Such set-ups typically comprise one or more distillation columns operated at temperatures and pressures specific to the azeotropic or near-azeotropic composition of interest. By fine tuning the temperature and pressure of the pressure swing distillation column(s), an azeotrope composition may be distilled from the column, wherein, depending on the pressure and temperature of the column, the resulting distillate may comprise the components of the azeotropic composition in different molar ratios than that of the original feed composition. This, therefore, can result in the liquid phase that is left in the column being richer in one component of the azeotropic composition than the other. In some cases, the liquid phase may be almost 100 mol% of the component left in the liquid phase.
An exemplary pressure swing apparatus set-up for the separation of azeotropic or near-azeotropic compositions of the invention is provided in Figure 1. This set-up comprises two columns (A and B), which are operated at different temperatures and pressures. Preferably, column A is operated at a lower pressure to the second column B. However, it is envisaged that column B may be operated at a lower pressure to column A. Similarly, column A is preferably operated at higher temperatures to column B. However, column B may just as easily be operated at higher temperatures to column A if the process requires.
In a specific embodiment, and with reference to Figure 1, a feed composition (Fi) comprising about 10 mol% to about 3 mol% 243db and about 90 mol% to about 97 mol% HF is fed into column A, which is operated at a pressure (Pa) of about 1 bara and temperatures of about 76 °C at the bottom (Tai) of the column and about 18 °C at the top (Ta2). Under these conditions, the Fi composition undergoes partial distillation, wherein a distillate composition (Ci) is distilled from the top of the column leaving a 243db rich residue (Di). After this first separation process, the Ci composition comprises about 3 mol% 243db and about 97 mol% HF. Whereas, the Di residue composition comprises about 99 to about 100 mol% 243db. The highly pure Di composition is removed from the column and collected, and the Ci composition is fed into column B, which is operated at a pressure (Pb) of about 20 bara and temperatures of about 129 °C at the bottom (Tbi) of the column and 121 °C at the top (Tb2). Under such conditions, the Ci composition undergoes distillation to provide a distillate composition (C2) comprising about 10 mol% to about 3 mol% 243db and about 90 mol% to about 97 mol% HF, which results in a HF rich residue (D2) remaining in the column. This D2 residue typically comprises about 99 mol% to about 100 mol% HF. After the separation process in column B, the highly pure D2 composition is removed from the column and collected, and the distillate composition C2 is recycled back into column A to repeat the process.
The graph in Figure 2 shows that the composition of the vapour phase and liquid phase of a 243db and HF binary mixture is the same, or essentially the same, in compositions wherein HF is present in an amount of from about 92 mol% to about 98 mol% and 243db is present in an amount of from about 8 mol% to about 2 mol% at pressures ranging from about 1 bar to about 10 bar, which is consistent with what would be expected of azeotropic compositions.
Examples Example 1 A binary azeotrope between 243db and HF was identified by a study of the vapour-liquid equilibrium of binary mixtures over a temperature range of -20°C to +70°C using a constant volume apparatus.
The experimental data were measured in a static constant volume apparatus consisting of a vessel of precisely known internal volume located in a temperature-controlled metal block. A magnetic stirring device was located inside the vessel. Refrigerated fluid was passed through the block to allow precise control of temperature inside the vessel. The cell was evacuated then known amounts of compositions of 243db and HF were charged to the cell. The temperature of the cell was then varied to temperatures between -20°C and +70°C. At each step the cell temperature and pressure were logged and recorded when stable conditions were reached.
The phase behaviour of these compositions at exemplary temperatures is illustrated in Figures 3 to 6, which show that a constant vapour pressure is reached at compositions wherein HF is present in an amount of from about 35 mol% to about 98 mol% and 243db is present in an amount of from about 65 mol% to about 2 mol%, which is consistent with what would be expected of azeotropic compositions. This trend is evidenced across all temperature ranges tested. A pressure maxima demonstrates the presence of a minimum boiling azeotrope. However, the constant vapour pressure (plateau region) suggests the present of two liquid phases within the azeotropic or near-azeotropic composition. Therefore, the azeotropic or near-azeotropic composition also comprises heteroazeotropic compositions where the vapour phase coexists with two liquid phases
Preferences and options for a given aspect, feature or parameter of the invention should, unless the context indicates otherwise, be regarded as having been disclosed in combination with any and all preferences and options for all other aspects, features and parameters of the invention.

Claims (26)

Claims
1. An azeotropic or near-azeotropic composition comprising HF and CH2CICHCICF3 (243db).
2. A composition according to Claim 1 consisting essentially of HF and 243db.
3. A composition according to Claim 1 or Claim 2 consisting of HF and 243db.
4. A composition according to any one of Claims 1 to 3 containing from about 10 mol% to about 99 mol% HF and from about 90 mol% to about 1 mol% 243db.
5. A composition according to Claim 4 comprising from about 20 mol% to about 99 mol% HF and from about 80 mol% to about 1 mol% 243db, such as about 30 mol% to about 99 mol% HF and from about 70 mol% to about 1 mol% 243db, for example about 40 mol% to about 99 mol% HF and from about 60 mol% to about 1 mol% 243db, preferably about 50 mol% to about 99 mol% HF and from about 50 mol% to about 1 mol% 243db, such as from about 60 mol% to about 99 mol% HF and from about 40 mol% to about 1 mol% 243db, for example from about 70 mol% to about 99 mol% HF and from about 30 mol% to about 1 mol% 243db, preferably from abou 80 mol% to about 99 mol% HF and from about 20 mol% to about 1 mol% 243db, such as from about 85 mol% to about 99 mol% HF and from about 15 mol% to about 1 mol% 243db, for example from about 90 mol% to about 99 mol% HF and from about 10 mol% to about 1 mol% 243db, such as from about 90 mol% to about 98 mol% HF and from about 10 mol% to about 2 mol% 243db and most preferably from about 92 mol% to about 98 mol% HF and from about 8 mol% to about 2 mol% 243db.
6. A composition according to any one of the preceding claims, wherein the azeotropic or near-azeotropic composition is present at temperatures of from about -20°C to about +90°C
7. A composition according to Claim 6, wherein the azeotropic or near-azeotropic composition is present at temperatures of from about -20°C to about +70°C, such as from about 0°C to about +70°C, preferably from temperatures of from about +30°C to about +70°C
8. A composition according to any one of the preceding claims, wherein the azeotropic or near-azeotropic composition is present at pressures of from about 0.5 bara to about 30 bara, for example from about 1 to about 10 bara.
9. The use of a composition (e.g. as an intermediate) according to any one of the preceding claims in the manufacture of one or more hydrofluoroolefins.
10. The use according to Claim 9, wherein the manufactured hydrofluoroolefin is one or both of CHFCHCFs (1234zeE) or CH2CFCF3 (1234yf).
11. A process for the separation of an azeotropic or near-azeotropic composition according to any one of Claims 1 to 8.
12. A process according to Claim 11, wherein the azeotropic or near-azeotropic composition is separated via the use of a pressure swing distillation.
13. A process according to Claims 11 or 12, wherein the pressure swing apparatus comprises two columns operated sequentially at different pressures.
14. A process according to any one of Claim 13, wherein the first column (A) is operated at a higher pressure to the second column (B).
15. A process according to Claim 12 to 14, wherein column A is operated at a pressure of from about 0.5 to about 15 bara, such as from about 0.5 to about 5 bara, preferably from about 0.5 to about 2 bara, for example about 1 bara.
16. A process according to any one of Claims 12 to 15, wherein column B is operated at a pressure of from about 1 to about 20 bara, such as from about 5 to about 20 bara, preferably from about 15 to about 20 bara, for example about 20 bara.
17. A process according to any one of Claims 12 to 16, wherein the two columns are operated sequentially at different temperatures.
18. A process according to Claim 17, wherein column A is operated at a temperature of from about 1°C to about 115 °C, such as from about 1 °C to about 80 °C, preferably from about 15 °C to about 80 °C.
19. A process according to Claims 17 or 18, wherein column B is operated at a temperature of from about 18 °C to about 203 °C, such as from about 67 °C to about 203 °C, preferably from about 109 °C to about 203 °C.
20. A process according to any one of Claims 12 to 19, wherein a composition (Fi) is fed into the process, wherein Fi comprises 50 mol% to about 97 mol% HF and from about 50 mol% to about 3 mol% 243db, advantageously from about 60 mol% to about 97 mol% HF and from about 40 mol% to about 3 mol% 243db, such as about 70 mol% to about 97 mol% HF and from about 30 mol% to about 3 mol% 243db, for example about 80 mol% to about 97 mol% HF and from about 20 mol% to about 3 mol% 243db, preferably about 90 mol% to about 97 mol% HF and from about 10 mol% to about 3 mol% 243db.
21. A process according to any one of Claims 12 to 20, wherein the Fi composition is separated into two liquid compositions in column A, wherein 243db is separated from the azeotrope composition to yield a composition (Di) comprising greater than about 90 mol% 243db, such as greater than about 95 mol% 243db, preferably greater than 99 mol% 243db, and an azeotropic or near-azeotropic composition (Ci) comprising 243db and HF in a molar ratio that is richer in HF than Fi.
22. A process according to any one of Claims 12 to 21, wherein Di is removed from the separating apparatus and Ci is fed into column B, wherein the Ci composition is separated into two further liquid compositions, wherein HF is separated from the azeotrope composition to yield a composition (D2) comprising greater than about 90 mol% HF, such as greater than about 95 mol% HF, preferably greater than 99 mol% HF, and an azeotropic or near-azeotropic composition (C2) comprising 243db and HF in a molar ratio that is richer in 243db than Ci.
23. A process according to any one of Claims 12 to 22, wherein composition D2 is removed from the separating apparatus and composition C2 is recycled back into column A.
24. A process according to any one of Claims 12 to 23, wherein the process is continuous.
25. A process according to any one of Claims 18 to 24, wherein the azeotropic or near-azeotropic composition is subjected to the separation process in column B first before being subjected to the separation process in column A.
26. Any novel composition, method or process as described herein, optionally with reference to the examples.
GB1615045.0A 2016-09-05 2016-09-05 Composition Withdrawn GB2546845A (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0940382A1 (en) * 1998-03-05 1999-09-08 Elf Atochem North America, Inc. Azeotrope of HF and 1,1,1-trifluro-3-chloro-2-propene
WO2002059231A2 (en) * 2001-01-24 2002-08-01 Honeywell International Inc. Azeotrope-like composition of 1,2-dichloro-3,3,3-trifluoropropene and hydrogen fluoride
EP2096096A1 (en) * 2008-02-26 2009-09-02 Honeywell International Inc. Azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244BB) and hydrogen fluoride (HF)
EP2098499A1 (en) * 2008-03-06 2009-09-09 Honeywell International Inc. Azeotrope-like composition of 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) and hydrogen fluoride (HF)
WO2010051327A2 (en) * 2008-10-31 2010-05-06 Honeywell International Inc. Azeotrope-like compositions of 1,1,2,3-tetrachloropropene and hydrogen fluoride
WO2014151448A2 (en) * 2013-03-15 2014-09-25 Honeywell International Inc. An improved integrated process to produce 2,3,3,3-tetrafluoropropene
EP2970741A1 (en) * 2013-03-13 2016-01-20 Honeywell International Inc. Azeotropic compositions of 1,3,3-trichloro-1,1-difluoropropane and hydrogen fluoride

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0940382A1 (en) * 1998-03-05 1999-09-08 Elf Atochem North America, Inc. Azeotrope of HF and 1,1,1-trifluro-3-chloro-2-propene
WO2002059231A2 (en) * 2001-01-24 2002-08-01 Honeywell International Inc. Azeotrope-like composition of 1,2-dichloro-3,3,3-trifluoropropene and hydrogen fluoride
EP2096096A1 (en) * 2008-02-26 2009-09-02 Honeywell International Inc. Azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244BB) and hydrogen fluoride (HF)
EP2098499A1 (en) * 2008-03-06 2009-09-09 Honeywell International Inc. Azeotrope-like composition of 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) and hydrogen fluoride (HF)
WO2010051327A2 (en) * 2008-10-31 2010-05-06 Honeywell International Inc. Azeotrope-like compositions of 1,1,2,3-tetrachloropropene and hydrogen fluoride
EP2970741A1 (en) * 2013-03-13 2016-01-20 Honeywell International Inc. Azeotropic compositions of 1,3,3-trichloro-1,1-difluoropropane and hydrogen fluoride
WO2014151448A2 (en) * 2013-03-15 2014-09-25 Honeywell International Inc. An improved integrated process to produce 2,3,3,3-tetrafluoropropene

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