CN101519580A - 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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- CN101519580A CN101519580A CNA2009101307336A CN200910130733A CN101519580A CN 101519580 A CN101519580 A CN 101519580A CN A2009101307336 A CNA2009101307336 A CN A2009101307336A CN 200910130733 A CN200910130733 A CN 200910130733A CN 101519580 A CN101519580 A CN 101519580A
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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
It is the rights and interests of 61/031,602 U.S. Provisional Patent Application that the application requires sequence number in application on February 26th, 2008, and is incorporated herein with way of reference.
Background of invention
Invention field
The present invention relates to 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (Azeotrope compositions F) and Azeotrope-like compositions, more specifically, the present invention relates to prepare 2,3,3, such Azeotrope compositions and the Azeotrope-like compositions of useful as intermediates in the 3-tetrafluoeopropene (HFO-1234yf).
Description of related art
Traditionally, Chlorofluorocarbons (CFCs) (CFCs) has been used as refrigeration agent, whipping agent and gaseous sterilization thinner as trichlorofluoromethane and Refrigerant 12.In recent years, perhaps the Chlorofluorocarbons (CFCs) of perhalogeno is paid close attention to widely to the harmful whole world that caused of ozonosphere of the earth.Therefore, need be to the safer equivalent material of stratosphere.Therefore, the whole world all contains less or does not have the fluorine of chlorine substituent to replace hydrocarbon make great efforts using.In this respect, have the dive 2-chloro-1,1,1 of value of low-ozone layer consumption, 2-tetrafluoropropane (HFO-244bb) be considered to Chlorofluorocarbons (CFCs) as the Refrigerant 12 that in coolant system, uses and as the whipping agent use the surrogate of trichlorofluoromethane.HFC ' s just 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 that meets the requirements on the environment of fire-extinguishing composite and power circulating working fluid is concerned about.Known in the art can the reaction by hydrogen fluoride and different hydrogen chlorocarbons prepares for example HCF ' s of fluorocarbon.Because HCFC (HCFC ' s) or Chlorofluorocarbons (CFCs) (CFC ' s) not zero ozone depletion, 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, compare nontoxic with chloride compound simultaneously.
HCFC-244bb is preparation 2,3,3, and the intermediate of 3-tetrafluoeopropene (HFO-1234yf) is described in U.S. Patent application 20070007488 and 20070197842, and is known in this field, and its specification sheets is attached among the application by reference.HFO-1234yf has been disclosed 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 pure substantially HFO-1234yf that important intermediate is a 2-chloro-1,1,1, the azeotropic or the Azeotrope-like compositions of 2-tetrafluoropropane (HCFC-244bb) and hydrogen fluoride (HF).In a single day this intermediate generates, and can be separated into its component subsequently by known abstraction technique.This azeotropic or Azeotrope-like compositions are not only preparation 2,3,3, and the intermediate of 3-tetrafluoeopropene (HFO-1234yf) also is the non-aqueous etchant mixture as etching semiconductor on electronic industry, and also as the composition of removing the oxidation on metal surface layer.In addition, the formation of HCFC-244bb and hydrofluoric azeotropic or Azeotrope-like compositions is for separating HCFC-244bb and impurity, halogen-carbon compound for example, and as 2,3,3, the 3-tetrafluoeopropene, 1,2-two chloro-3,3,3-trifluoro propene, or 1,1,1,2, the 2-pentafluoropropane is useful.When needs separate the mixture of HCFC-244bb and impurity, add HF to form the azeotropic mixture of HCFC-244bb and HF, impurity passes through as distillation then, and washing or other known method are removed from azeotropic mixture.
Summary of the invention
The invention provides a kind of basically by hydrogen fluoride and 2-chloro-1,1,1, azeotropic or Azeotrope-like compositions that the 2-tetrafluoropropane is formed.
The present invention further provides a kind of azeotropic or Azeotrope-like compositions, it is basically by the hydrogen fluoride of about 50 weight percents of about 1-and the 2-chloro-1,1,1 of about 99 weight percents of about 50-, and the 2-tetrafluoropropane is formed.In the following time of pressure of the about 103psia of about 14psia-, the boiling point of said composition is about 61 ℃ of about 0C-.
The present invention also provides a kind of method for preparing azeotropic or Azeotrope-like compositions, it comprises and forms one basically by the hydrogen fluoride of about 50 weight percents of about 1-and the 2-chloro-1 of about 99 weight percents of about 50-, 1,1, the mixture that the 2-tetrafluoropropane is formed, thus the boiling point that is formed under the pressure of the about 103psia of about 14psia-is about 0 ℃-Yue 61 ℃ azeotropic or Azeotrope-like compositions.
The present invention also further provides a kind of 2-chloro-1,1,1 of removing from mixture, the method of 2-tetrafluoropropane, this mixture contains 2-chloro-1,1,1,2-tetrafluoropropane and at least a impurity, this method is included in to add in this mixture effectively decides to form 2-chloro-1,1,1, the hydrogen fluoride of the amount of 2-tetrafluoropropane and hydrofluoric azeotropic or Azeotrope-like compositions separates this Azeotrope compositions subsequently from impurity.
The accompanying drawing summary
Fig. 1 is presented at 0 ℃, 25 ℃ and 61 ℃ of steam pressure value figure that measure the mixture of embodiment 2 formation down.
Detailed Description Of The Invention
In a kind of method for preparing the HCFC-244bb precursor, reagent is fluoridized with hydrogen fluoride. For example, by Liquid phase or gas phase catalysis CF3CCl＝CH
2(HCFO-1233xf) and HF fluoridize to obtain HCFC-244bb Feasible. These methods are open in U.S. Patent application 20070007488 and 20070197842. This The product of a little precursors comprises HCFC-244bb, unreacted HF and other accessory substances. By removing by-product Thing, binary azeotropic or the Azeotrope-like compositions of formation HCFC-244bb and HF. Then this binary azeotropic or class Azeotrope compositions is separable into its component. The azeotropic of HCFC-244bb and HF or Azeotrope-like compositions are also available Make the recycle of fluorination reactor. Therefore, for example in the process of preparation HCFC-244bb, can reclaim Part HCFC-244bb is as azeotropic or the Azeotrope-like compositions of HCFC-244bb and HF, and recirculation should Composition is in reactor.
HCFC-244bb and HF form azeotropic or Azeotrope-like compositions. The thermodynamic state of fluid is by its pressure Power, temperature, liquid form and vapour composition is determined. For a kind of true Azeotrope compositions, in given temperature In degree and the pressure limit, liquid forms and vapor phase equates basically. In fact this means in phase transformation These components can not be separated in the process. According to purpose of the present invention, azeotropic mixture is a kind of with respect to encircling on every side The boiling point of the component of mixture in border demonstrates the liquid mixture of the highest or minimum boiling point. Azeotropic or class Azeotrope compositions is a kind of mixture that two or more different components are arranged, wherein these groups under setting pressure Divide to exist with liquid form more being higher than or more being lower than under the temperature of each component boiling temperature in substantial constant Boiling, and in boiling process, can produce the vapour composition substantially the same with the liquid composition. According to the present invention Purpose, Azeotrope compositions is defined as and contains Azeotrope-like compositions, namely this Azeotrope-like compositions has and azeotropic The similar character of composition that is to say, have constant boiling point characteristic or the boiling or evaporation conditions under do not have The trend that fractionation is arranged. Therefore, the vapour composition that forms in boiling or evaporation forms identical with original liquid Or substantially the same. Therefore, in the process of boiling or evaporation, this liquid component, if change, Changing also only is Min. or negligible degree. This and non-Azeotrope-like compositions are in boiling or evaporation Liquid forms marked change formation contrast in the process. Therefore, the principal character of azeotropic mixture and Azeotrope-like compositions Be: under given pressure, the boiling point that liquid forms is fixed, and the vapour composition base of boiling composition Be the composition that the liquid that can seethe with excitement forms on the basis, the composition fractionation of liquid component does not just take place substantially. When Azeotrope compositions or Azeotrope-like compositions seethe with excitement under different pressures, each component in the Azeotrope compositions Boiling point and percentage by weight may change. Therefore, azeotropic or Azeotrope-like compositions can be according to existence Relation between its component, or according to the compositing range of component, or according to fixing to have under the specified pressure Boiling point is that the accurate percentage by weight of every kind of component of the composition of feature is defined.
The invention provides a kind of hydrogen fluoride and HCFC-244bb that includes effective dose is total to form azeotropic or class The composition of composition boils. Effective dose refers to that every kind of component forms azeotropic or class when mixing with other component The consumption of Azeotrope compositions. The present composition is preferably basically only by hydrogen fluoride and HCFC-244bb group The binary azeotrope that becomes.
One preferred embodiment in, composition of the present invention contains the 1-that has an appointment about 50 percentage by weights HF preferably from about 15 percentage by weights to about 40 percentage by weights, is more preferably about 22 percentage by weights and arrives About 33 percentage by weights are based on the weighing scale of azeotropic or Azeotrope-like compositions.
One preferred embodiment in, composition of the present invention contains the HCFC-244bb of about 99 weight percents of the 50-that has an appointment, preferably about 60 weight percents are to about 85 weight percents, be more preferably about 67 weight percents to about 78 weight percents, based on the weight meter of azeotropic or Azeotrope-like compositions.
The composition of the present invention preferably boiling point under the about 103psia pressure of about 14psia-is about 61 ℃ of about 0C-.In one embodiment, the boiling point under the pressure of about 14psia is about 0C.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 ℃.The azeotropic of the HCFC-244bb of a kind of HF that contains 27 ± 2 weight percents of having an appointment and about 73 ± 2 weight percents or the boiling point of Azeotrope-like compositions are 23 ℃.
In another embodiment of the invention, 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) can be separated in the mixture of 2-tetrafluoropropane (HCFC-244bb) and impurity from containing 2-chloro-1,1,1.Impurity wherein for example, by preparation 2-chloro-1,1,1, the production stage of 2-tetrafluoropropane (HCFC-244bb) forms.By at 2-chloro-1,1,1, add hydrogen fluoride in the mixture of 2-tetrafluoropropane (HCFC-244bb) and impurity and realize separating.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 the mixture, this Azeotrope compositions for example passes through distillation subsequently, and washing or other separation means known in the art are separated from impurity.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.Typical 2-chloro-1,1,1, the impurity of 2-tetrafluoropropane (HCFC-244bb) comprise other can with 2-chloro-1,1,1, the miscible halohydrocarbon of 2-tetrafluoropropane (HCFC-244bb) for example 2,3,3,3-tetrafluoeopropene; 1,1,1,2,2-pentafluoropropane or 1,2-two chloro-3,3,3-trifluoro propene.
Following non-limiting example is used to illustrate the present invention.
Embodiment 1
The 2-chloro-1,1,1 of 73g, 2-tetrafluoropropane (HCFC-244bb) is mixed with the HF of 27g, to form heterogeneous azeotropic mixture.The vapour pressure of this mixture is about 37psia under about 25 ℃.
Embodiment 2
To only contain 2-chloro-1,1,1, the binary composition of 2-tetrafluoropropane (HCFC-244bb) and HF mixes, to form the different heterogeneous Azeotrope compositions of forming.Respectively at about 0 ℃, 25 ℃ and 61 ℃ of vapour pressures of measuring these mixtures, the result is as follows.Table 1 has been represented at about 0 ℃, under 25 ℃ and the 61 ℃ of constant temps as the function of composition with 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 show that also this mixture is 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 the HCFC-244bb and the HF of Individual existence, just shown in first row and last column of table 1, when HF be 0.0wt.% and 244bb be 100.0wt.% and when 244bb be that 0.0wt.% and HF are when 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 the 2-of 23 ℃ of following 60g chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) is mixed 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.The result shows the HF that contains the 27 ± 2wt% that has an appointment at 23 ℃ of following these Azeotrope compositions.
Although the present invention is embodiment preferred and specifically show and illustrate by reference, the method that the present invention utilizes those of ordinary skill to know can be carried out multiple change and modification and do not deviated from the spirit and scope of the present invention.Claim will contain, and disclosed embodiment, discussed above those supply to select embodiment and all equal modes thereof.
Claims (15)
1, a kind of azeotropic or Azeotrope-like compositions, it is basically by hydrogen fluoride and 2-chloro-1,1,1, and the 2-tetrafluoropropane is formed.
2, a kind of azeotropic or Azeotrope-like compositions, it is basically by based on the hydrogen fluoride of about 50 weight percents of the about 1-of weight meter of this azeotropic or Azeotrope-like compositions and the 2-chloro-1 of about 99 weight percents of about 50-, 1,1, the 2-tetrafluoropropane is formed, said composition is under the pressure of the about 103psia of about 14psia-, and boiling point is about 0 ℃-Yue 61 ℃.
3, composition as claimed in claim 2, said composition are by hydrogen fluoride and 2-chloro-1,1,1, and the 2-tetrafluoropropane is formed.
4, a kind of method for preparing azeotropic or Azeotrope-like compositions, this method comprises the formation mixture, and this mixture is gone up substantially by the hydrogen fluoride of about 50 weight percents of about 1-and the 2-chloro-1,1,1 of about 99 weight percents of about 50-, and the 2-tetrafluoropropane is formed.
5, method as claimed in claim 4, wherein said composition are by hydrogen fluoride and 2-chloro-1,1,1, and the 2-tetrafluoropropane is formed.
6, method as claimed in claim 4, this method also comprise by transformation distillation from 2-chloro-1,1,1, separates 2-chloro-1,1,1, the step of 2-tetrafluoropropane in 2-tetrafluoropropane and hydrofluoric azeotropic or the Azeotrope-like compositions.
7, method as claimed in claim 4, this method also are included in and add 2-chloro-1,1,1, the step of 2-tetrafluoropropane and hydrofluoric azeotropic or Azeotrope-like compositions in the fluorination reactor.
8, a kind of from containing 2-chloro-1,1,1, separate 2-chloro-1 in the mixture of 2-tetrafluoropropane and at least a impurity, 1,1, the method for 2-tetrafluoropropane, this 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 separate this Azeotrope compositions thereafter with impurity.
9, method as claimed in claim 8, 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, method as claimed in claim 8, 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, method as claimed in claim 8, wherein said impurity comprises halohydrocarbon.
12, method as claimed in claim 8, wherein said impurity and 2-chloro-1,1,1, the 2-tetrafluoropropane is miscible.
13, method as claimed in claim 8, wherein said impurity comprises 2,3,3,3-tetrafluoeopropene, 1,1,1,2,2-pentafluoropropane and 1,2-two chloro-3,3,3, one or more kinds in-trifluoro propene.
14, method as claimed in claim 8, wherein said separation is undertaken by distillation.
15, method as claimed in claim 8, wherein said Azeotrope compositions are basically by the hydrogen fluoride of about 50 weight percents of about 1-and the 2-chloro-1,1,1 of about 99 weight percents of about 50-, and the 2-tetrafluoropropane is formed.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3160208P | 2008-02-26 | 2008-02-26 | |
| US61/031,602 | 2008-02-26 | ||
| US61/031602 | 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 true CN101519580A (en) | 2009-09-02 |
| CN101519580B CN101519580B (en) | 2014-01-29 |
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| CN200910130733.6A Active CN101519580B (en) | 2008-02-26 | 2009-02-25 | Azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane (hcfc-244bb) and hydrogen fluoride (hf) |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103626626A (en) * | 2013-11-01 | 2014-03-12 | 西安近代化学研究所 | Separating method of mixture of hydrogen fluoride and 2-chlorine-1,1,1,2-tetrafluoropropane |
| CN111433178A (en) * | 2017-11-20 | 2020-07-17 | Ａｇｃ株式会社 | Purification method of (Z) -1-chloro-2, 3,3, 3-tetrafluoropropene |
| CN112778974A (en) * | 2019-11-06 | 2021-05-11 | 霍尼韦尔国际公司 | Azeotrope or azeotrope-like composition of 2-chloro-1, 1,1, 2-tetrafluoropropane 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 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103626626A (en) * | 2013-11-01 | 2014-03-12 | 西安近代化学研究所 | Separating method of mixture of hydrogen fluoride and 2-chlorine-1,1,1,2-tetrafluoropropane |
| 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 |
| CN111433178A (en) * | 2017-11-20 | 2020-07-17 | Ａｇｃ株式会社 | Purification method of (Z) -1-chloro-2, 3,3, 3-tetrafluoropropene |
| CN112778974A (en) * | 2019-11-06 | 2021-05-11 | 霍尼韦尔国际公司 | Azeotrope or azeotrope-like composition of 2-chloro-1, 1,1, 2-tetrafluoropropane and water |
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| Publication number | Publication date |
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| CN101519580B (en) | 2014-01-29 |
| ES2364802T3 (en) | 2011-09-14 |
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