CN101519580B - Azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane (hcfc-244bb) and hydrogen fluoride (hf) - Google Patents
Azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane (hcfc-244bb) and hydrogen fluoride (hf) Download PDFInfo
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- CN101519580B CN101519580B CN200910130733.6A CN200910130733A CN101519580B CN 101519580 B CN101519580 B CN 101519580B CN 200910130733 A CN200910130733 A CN 200910130733A CN 101519580 B CN101519580 B CN 101519580B
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Abstract
The present invention provides an azeotropic and azeotrope-like compositions of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (HF). Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
Description
the cross reference of related application
The rights and interests of the U.S. Provisional Patent Application that the sequence number that the application's requirement was applied on February 26th, 2008 is 61/031,602, and be incorporated herein with way of reference.
Background of invention
Description of related art
Traditionally, Chlorofluorocarbons (CFCs) (CFCs) is if trichlorofluoromethane and Refrigerant 12 are as refrigeration agent, whipping agent and gaseous sterilization thinner.In recent years, perhaps the Chlorofluorocarbons (CFCs) of perhalogeno has caused that to the ozonosphere of the earth is harmful the whole world pays close attention to widely.Therefore, need to be to the safer equivalent material of stratosphere.Therefore, the whole world is all used and is contained less or do not have the fluorine of chlorine substituent to replace hydrocarbon in effort.In this respect, have the consumption of low-ozone layer dive the 2-chloro-1,1,1,2-tetrafluoropropane (HFO-244bb) of value be considered to Chlorofluorocarbons (CFCs) as the Refrigerant 12 using in coolant system and as whipping agent use the surrogate of trichlorofluoromethane.HFC ' s, namely only contains carbon, and the preparation of the compound of hydrogen and fluorine has become to provide and can be used for solvent, whipping agent, refrigeration agent, sanitising agent, aerosol propellant, heat-transfer medium, dielectric medium, the theme that the product meeting the requirements on the environment of fire-extinguishing composite and power circulating working fluid is concerned about.Known in the artly can react to prepare for example HCF ' s of fluorocarbon by hydrogen fluoride and different hydrogen chlorocarbons.Because HCFC (HCFC ' s) or Chlorofluorocarbons (CFCs) (CFC ' s) are not zero ozone depletions, therefore these HCF ' s are considered to be not only than more environmental protection of HCFC (HCFC ' s) or Chlorofluorocarbons (CFCs) (CFC ' s), and they are fire-retardant, simultaneously and chloride Compound Phase than nontoxic.
HCFC-244bb is the intermediate of preparation 2,3,3,3-tetrafluoeopropene (HFO-1234yf), in U.S. Patent application 20070007488 and 20070197842, describes, and is known in this field, and its specification sheets is attached in the application by reference.HFO-1234yf has been published as effective refrigeration agent, fire-fighting medium, heat-transfer medium, propelling agent, pore forming material, whipping agent, gaseous dielectric medium, sterilant carrier, polymerisation medium, the fluid that particle removes, carrier fluid, polishing abrasive, displacement siccative and power circulating working fluid.
Have now found that in the preparation of substantially pure HFO-1234yf, important intermediate is azeotropic or the Azeotrope-like compositions of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (HF).Once this intermediate generates, and can be separated into by known abstraction technique its component subsequently.This azeotropic or Azeotrope-like compositions are not only preparation 2, the intermediate of 3,3,3-tetrafluoeopropene (HFO-1234yf), also be the non-aqueous etchant mixture as etching semiconductor in electronic industry, and also as the composition of removing oxidation on metal surface layer.In addition, the formation of HCFC-244bb and hydrofluoric azeotropic or Azeotrope-like compositions is for separated HCFC-244bb and impurity, halogen-carbon compound for example, and as 2,3,3,3-tetrafluoeopropene, 1,2-bis-is chloro-3,3,3-trifluoro propene, or 1,1,1,2,2-pentafluoropropane is useful.When the mixture of the separated HCFC-244bb of needs and impurity, add HF to form the azeotropic mixture of HCFC-244bb and HF, then impurity by as distillation, washing or other known method are removed from azeotropic mixture.
Invention field
The present invention relates to 2-chloro-1,1,1, Azeotrope compositions and the Azeotrope-like compositions of 2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (HF), more specifically, the present invention relates to prepare 2,3, useful such Azeotrope compositions and the Azeotrope-like compositions of intermediate in 3,3-tetrafluoeopropene (HFO-1234yf).
Summary of the invention
The invention provides a kind of azeotropic or Azeotrope-like compositions substantially being formed by hydrogen fluoride and 2-chloro-1,1,1,2-tetrafluoropropane.
The present invention further provides a kind of azeotropic or Azeotrope-like compositions, it is comprised of the hydrogen fluoride of about 1-approximately 50 weight percents and the 2-chloro-1,1,1,2-tetrafluoropropane of about 50-approximately 99 weight percents substantially.In the time of under the pressure of the about 103psia of about 14psia-, the boiling point of said composition is approximately 0 ℃-Yue 61 ℃.
The present invention also provides a kind of method of preparing azeotropic or Azeotrope-like compositions, it comprises and forms one substantially by the hydrogen fluoride of about 1-approximately 50 weight percents and the 2-chloro-1 of about 50-approximately 99 weight percents, 1,1, the mixture that 2-tetrafluoropropane forms is azeotropic or the Azeotrope-like compositions of approximately 0 ℃-Yue 61 ℃ thereby be formed on boiling point under the pressure of the about 103psia of about 14psia-.
The present invention also further provides a kind of 2-chloro-1,1,1 that removes from mixture, the method of 2-tetrafluoropropane, this mixture contains 2-chloro-1,1,1,2-tetrafluoropropane and at least one impurity, the method is included in this mixture and adds and effectively determine to form 2-chloro-1,1,1, the hydrogen fluoride of the amount of 2-tetrafluoropropane and hydrofluoric azeotropic or Azeotrope-like compositions, subsequently that this Azeotrope compositions is separated from impurity.
Accompanying drawing summary
Fig. 1 is presented at 0 ℃, measures the steam pressure value figure of the mixture that embodiment 2 forms at 25 ℃ and 61 ℃.
Detailed Description Of The Invention
In a kind of method of preparing HCFC-244bb precursor, reagent is fluoridized with hydrogen fluoride.For example,, by liquid phase or gas phase catalysis CF
3cCl=CH
2(HCFO-1233xf) and HF fluoridize that to obtain HCFC-244bb be feasible.These methods are open in U.S. Patent application 20070007488 and 20070197842.The reaction product of these precursors comprises HCFC-244bb, unreacted HF and other by products.By removing by product, form binary azeotropic or the Azeotrope-like compositions of HCFC-244bb and HF.Then this binary azeotropic or Azeotrope-like compositions are separable into its component.The azeotropic of HCFC-244bb and HF or Azeotrope-like compositions also can be used as the recycle of fluorination reactor.Therefore, for example, in the process of preparation HCFC-244bb, can recovery part HCFC-244bb as azeotropic or the Azeotrope-like compositions of HCFC-244bb and HF, and recirculation said composition is in reactor.
HCFC-244bb and HF form azeotropic or Azeotrope-like compositions.The thermodynamic state of fluid consists of its pressure, temperature, liquid and vapor composition is determined.For a kind of true Azeotrope compositions, within the scope of given temperature and pressure, liquid forms and vapor phase equates substantially.In fact this means that these components can not be separated in phase transition process.According to object of the present invention, azeotrope is a kind of boiling point of the component of mixture with respect to surrounding environment, demonstrates the liquid mixture of the highest or minimum boiling point.Azeotropic or Azeotrope-like compositions are a kind of mixtures that has two or more different componentss, wherein under setting pressure, these components exist with liquid form, substantially constant more higher than or more at the temperature lower than each component boiling temperature, seethe with excitement, and can produce and form substantially the same vapor composition with liquid in boiling process.According to object of the present invention, Azeotrope compositions is defined as and contains Azeotrope-like compositions, and this Azeotrope-like compositions has and the similar character of Azeotrope compositions, that is to say, has constant boiling point characteristic or under boiling or evaporation conditions, there is no the trend of fractionation.Therefore the vapor composition, forming in boiling or evaporation forms identical or substantially the same with original liquid.Therefore, in the process of boiling or evaporation, this liquid ingredient, if changed, changing is only also inferior limit or negligible degree.This and non-Azeotrope-like compositions liquid in boiling or evaporative process forms noticeable change and forms contrast.Therefore, the principal character of azeotrope and Azeotrope-like compositions is: under given pressure, the boiling point that liquid forms is fixed, and the vapor composition that forms of boiling is the composition that the liquid that can seethe with excitement forms substantially, and the composition fractionation of liquid ingredient does not namely occur substantially.When Azeotrope compositions or Azeotrope-like compositions seethe with excitement under different pressures, in Azeotrope compositions, the boiling point of each component and weight percent may change.Therefore, azeotropic or Azeotrope-like compositions, can be according to the relation being present between its component, or according to the compositing range of component, or is defined according to take the accurate weight percent under specified pressure with every kind of component of the composition that fixedly boiling point is feature.
The invention provides a kind of hydrogen fluoride that includes significant quantity and HCFC-244bb to form the composition of azeotropic or Azeotrope-like compositions.Significant quantity refers to that every kind of component forms the consumption of azeotropic or Azeotrope-like compositions when mixing with other component.The present composition is preferably the binary azeotrope being substantially only comprised of hydrogen fluoride and HCFC-244bb.
One preferred embodiment in, composition of the present invention is containing the HF of 1-approximately 50 weight percents of having an appointment, preferably, from approximately 15 weight percents to approximately 40 weight percents, be more preferably approximately 22 weight percents to approximately 33 weight percents, the weighing scale based on azeotropic or Azeotrope-like compositions.
One preferred embodiment in, composition of the present invention is containing the HCFC-244bb of 50-approximately 99 weight percents of having an appointment, preferably approximately 60 weight percents are to approximately 85 weight percents, be more preferably approximately 67 weight percents to approximately 78 weight percents, the weighing scale based on azeotropic or Azeotrope-like compositions.
The composition of the present invention preferably boiling point under the about 103psia pressure of about 14psia-is approximately 0 ℃-Yue 61 ℃.In one embodiment, the boiling point under the pressure of about 14psia is about 0 ℃.In another embodiment, the boiling point under the pressure of about 37psia is about 25 ℃.In another embodiment, the boiling point under the pressure of about 103psia is about 61 ℃.A kind of azeotropic of HCFC-244bb or boiling point of Azeotrope-like compositions containing the have an appointment HF of 27 ± 2 weight percents and approximately 73 ± 2 weight percents is 23 ℃.
In another embodiment of the invention, 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) can be separated from the mixture that contains 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and impurity.Impurity wherein for example, is formed by the production stage of preparing 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb).Separated by adding hydrogen fluoride to realize in the mixture at 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and impurity.To be enough to form 2-chloro-1,1,1, the hydrogen fluoride of the amount of the Azeotrope compositions of 2-tetrafluoropropane (HCFC-244bb) and HF is added in mixture, this Azeotrope compositions, for example, by distillation, washs or the separation from impurity of other separation means known in the art subsequently.In one embodiment, impurity itself not with 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), hydrogen fluoride, or 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrofluoric mixture form azeotropic mixture.In another concrete enforcement, impurity and 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb), hydrogen fluoride or 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrofluoric mixture form azeotropic mixture.The impurity of typical 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) comprises halohydrocarbon that other can be miscible with 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) for example 2,3,3,3-tetrafluoeopropene; 1,1,1,2,2-pentafluoropropane or 1,2-bis-are chloro-3,3,3-trifluoro propene.
Following non-limiting example is used for illustrating the present invention.
embodiment 1
The 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) of 73g mixes with the HF of 27g, to form heterogeneous azeotropic mixture.At approximately 25 ℃, the vapour pressure of this mixture is about 37psia.
embodiment 2
The binary composition that will only contain 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and HF mixes, to form the different heterogeneous Azeotrope compositions that form.Respectively at approximately 0 ℃, 25 ℃ and 61 ℃ of vapour pressures of measuring these mixtures, result is as follows.Table 1 has represented at approximately 0 ℃, under 25 ℃ and 61 ℃ of constant temps as the function with the composition of the HF that changes weight percent, P-T-X balance each other, HCFC-244bb and HF vapor pressure measurement value, it is multiphase mixture that this data presentation goes out HCFC-244bb/HF.
The P-T-X of table 1:HCFC-244bb/HF system
These data also show this mixture be azeotropic or class azeotropic, this is because under all blending ratios of listing, the vapour pressure of this HCFC-244bb and HF mixture is greater than the vapour pressure of HCFC-244bb and the HF of Individual existence, namely as shown in the first row of table 1 and last column, when HF be 0.0wt.% and 244bb be 100.0wt.% and when 244bb be that 0.0wt.% and HF are while being 100.0wt.%.The data of table 1 present with diagram form at Fig. 1.
embodiment 3
The azeotropic of this HCFC-244bb/HF mixture or Azeotrope-like compositions also can be verified by solution-air-liquid balance (VLLE).At 23 ℃, the 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) of 60g mixes with the HF of 30g, the mixture of heterogeneous to form (range estimation).To gas composition, the liquid on upper strata (rich HF), the liquid of bottom (organically) sampling.Result shows that this Azeotrope compositions is containing the HF of the 27 ± 2wt% that has an appointment at 23 ℃.
Although the preferred by reference embodiment of the present invention and specifically show and illustrate, the present invention utilizes method that those of ordinary skill is known can carry out multiple change and modification and does not deviate from the spirit and scope of the present invention.Claim will contain published embodiment, discussed above those supply to select embodiment and all equal modes thereof.
Claims (15)
1. azeotropic or an Azeotrope-like compositions, it is comprised of hydrogen fluoride and 2-chloro-1,1,1,2-tetrafluoropropane substantially.
2. an azeotropic or Azeotrope-like compositions, it is substantially by the hydrogen fluoride of weighing scale 1-50 weight percent based on this azeotropic or Azeotrope-like compositions and the 2-of 50-99 weight percent chloro-1,1,1,2-tetrafluoropropane forms, said composition is under the pressure of 14psia-103psia, and boiling point is 0 ℃-61 ℃.
3. azeotropic as claimed in claim 2 or Azeotrope-like compositions, said composition is comprised of hydrogen fluoride and 2-chloro-1,1,1,2-tetrafluoropropane.
4. a method of preparing azeotropic or Azeotrope-like compositions, the method comprises formation mixture, the 2-chloro-1,1,1,2-tetrafluoropropane that this mixture is gone up substantially by the hydrogen fluoride of 1-50 weight percent and 50-99 weight percent forms.
5. the method for preparing azeotropic or Azeotrope-like compositions as claimed in claim 4, wherein said composition is comprised of hydrogen fluoride and 2-chloro-1,1,1,2-tetrafluoropropane.
6. the method for preparing azeotropic or Azeotrope-like compositions as claimed in claim 4, the method also comprises by transformation distills the step with separated 2-chloro-1,1,1,2-tetrafluoropropane hydrofluoric azeotropic or Azeotrope-like compositions from 2-chloro-1,1,1,2-tetrafluoropropane.
7. the method for preparing azeotropic or Azeotrope-like compositions as claimed in claim 4, the method is also included in the step that adds 2-chloro-1,1,1,2-tetrafluoropropane and hydrofluoric azeotropic or Azeotrope-like compositions in fluorination reactor.
8. one kind from containing 2-chloro-1,1,1, in the mixture of 2-tetrafluoropropane and at least one impurity, separated 2-chloro-1, the method of 1,1,2-tetrafluoropropane, the method comprises hydrogen fluoride is joined in this mixture, described hydrofluoric amount is enough to form 2-chloro-1,1,1,2-tetrafluoropropane and hydrofluoric azeotropic or Azeotrope-like compositions, thereafter that this Azeotrope compositions is separated with impurity.
9. as claimed in claim 8 from containing 2-chloro-1,1,1, in the mixture of 2-tetrafluoropropane and at least one impurity, separated 2-chloro-1,1,1, the method of 2-tetrafluoropropane, wherein said impurity not with 2-chloro-1,1,1,2-tetrafluoropropane, hydrogen fluoride or 2-chloro-1,1,1,2-tetrafluoropropane and hydrofluoric mixture form azeotropic mixture.
10. as claimed in claim 8 from containing 2-chloro-1,1,1, in the mixture of 2-tetrafluoropropane and at least one impurity, separated 2-chloro-1,1,1, the method of 2-tetrafluoropropane, wherein said impurity and 2-chloro-1,1,1,2-tetrafluoropropane, hydrogen fluoride or 2-chloro-1,1,1,2-tetrafluoropropane and hydrofluoric mixture form azeotropic mixture.
11. as claimed in claim 8 from the mixture that contains 2-chloro-1,1,1,2-tetrafluoropropane and at least one impurity the method for separated 2-chloro-1,1,1,2-tetrafluoropropane, wherein said impurity comprises halohydrocarbon.
12. as claimed in claim 8 from the mixture that contains 2-chloro-1,1,1,2-tetrafluoropropane and at least one impurity the method for separated 2-chloro-1,1,1,2-tetrafluoropropane, wherein said impurity and 2-chloro-1,1,1,2-tetrafluoropropane are miscible.
13. as claimed in claim 8 from the mixture that contains 2-chloro-1,1,1,2-tetrafluoropropane and at least one impurity separated 2-chloro-1, the method of 1,1,2-tetrafluoropropane, wherein said impurity comprises 2,3,3,3-tetrafluoeopropene, 1,1,1,2,2-pentafluoropropane and 1,2-bis-chloro-3,3,3, one or more of in-trifluoro propene.
14. as claimed in claim 8 from the mixture that contains 2-chloro-1,1,1,2-tetrafluoropropane and at least one impurity the method for separated 2-chloro-1,1,1,2-tetrafluoropropane, wherein said separation is undertaken by distillation.
15. is as claimed in claim 8 from containing 2-chloro-1,1, in the mixture of 1,2-tetrafluoropropane and at least one impurity, separated 2-chloro-1,1,1, the method of 2-tetrafluoropropane, wherein said Azeotrope compositions is substantially by the hydrogen fluoride of 1-50 weight percent and the 2-of 50-99 weight percent chloro-1,1,1,2-tetrafluoropropane forms.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3160208P | 2008-02-26 | 2008-02-26 | |
| US61/031602 | 2008-02-26 | ||
| US61/031,602 | 2008-02-26 | ||
| US12/368,395 | 2009-02-10 | ||
| US12/368395 | 2009-02-10 | ||
| US12/368,395 US8070975B2 (en) | 2008-02-26 | 2009-02-10 | Azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (HF) |
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| CN101519580A CN101519580A (en) | 2009-09-02 |
| CN101519580B true CN101519580B (en) | 2014-01-29 |
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| CN103626626B (en) * | 2013-11-01 | 2015-06-24 | 西安近代化学研究所 | Separating method of mixture of hydrogen fluoride and 2-chlorine-1,1,1,2-tetrafluoropropane |
| EP3715337A4 (en) * | 2017-11-20 | 2021-08-11 | AGC Inc. | Method for purifying (z)-1-chloro-2,3,3,3-tetrafluoropropene |
| WO2021090071A1 (en) * | 2019-11-06 | 2021-05-14 | Honeywell International Inc. | Azeotrope or azeotrope-like compositions of 2-chloro-1,1,1,2-tetrafluoropropane (hcfc-244bb) and water |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107267A (en) * | 1997-08-25 | 2000-08-22 | E. I. Du Pont De Nemours And Company | Compositions comprising CF3 CF2 CHF2 and their manufacture |
| CN1514817A (en) * | 2001-01-24 | 2004-07-21 | 霍尼韦尔国际公司 | Azeotrope-like composition of 1-chloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
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2009
- 2009-02-12 ES ES09152743T patent/ES2364802T3/en active Active
- 2009-02-25 CN CN200910130733.6A patent/CN101519580B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107267A (en) * | 1997-08-25 | 2000-08-22 | E. I. Du Pont De Nemours And Company | Compositions comprising CF3 CF2 CHF2 and their manufacture |
| CN1514817A (en) * | 2001-01-24 | 2004-07-21 | 霍尼韦尔国际公司 | Azeotrope-like composition of 1-chloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
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