JP3182869B2 - Azeotropic mixture of pentafluoroethane and pentafluorochloroethane and method for separating pentafluorochloroethane - Google Patents
Azeotropic mixture of pentafluoroethane and pentafluorochloroethane and method for separating pentafluorochloroethaneInfo
- Publication number
- JP3182869B2 JP3182869B2 JP12460892A JP12460892A JP3182869B2 JP 3182869 B2 JP3182869 B2 JP 3182869B2 JP 12460892 A JP12460892 A JP 12460892A JP 12460892 A JP12460892 A JP 12460892A JP 3182869 B2 JP3182869 B2 JP 3182869B2
- Authority
- JP
- Japan
- Prior art keywords
- pentafluorochloroethane
- mixture
- distillation
- pentafluoroethane
- separating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- 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
- C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
-
- 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
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ペンタフルオロエタン
(以下、Ｒ−１２５と称する。)とペンタフルオロクロロ
エタン(以下、Ｒ−１１５と称す。)の共沸混合物、およ
び、Ｒ−１２５およびＲ−１１５を含んで成る混合物か
らＲ−１１５を分離する方法に関する。Ｒ−１２５は、
クロロジフルオロメタンの代替冷媒として着目されてい
る。The present invention relates to pentafluoroethane.
(Hereinafter referred to as R-125) and azeotropic mixture of pentafluorochloroethane (hereinafter referred to as R-115) and a mixture comprising R-125 and R-115. About the method. R-125 is
It is receiving attention as an alternative refrigerant to chlorodifluoromethane.
【０００２】[0002]
【従来の技術および発明が解決すべき課題】Ｒ−１２５
は、通常、テトラクロロエチレンなどの塩化炭素とフッ
化水素（ＨＦ）を反応させることにより製造される。こ
の際に、副生するＲ−１１５はオゾンを破壊する物質で
あるため除去しなければならない。しかし、これまでに
Ｒ−１２５およびＲ−１１５を含んで成る混合物からＲ
−１１５を分離する方法はいかなる文献にも記載されて
いない。2. Description of the Related Art R-125
Is usually produced by reacting carbon chloride such as tetrachloroethylene with hydrogen fluoride (HF). At this time, R-115 as a by-product must be removed because it is a substance that destroys ozone. However, to date, mixtures comprising R-125 and R-115 have
No method for separating -115 is described in any literature.
【０００３】[0003]
【課題を解決するための手段】本発明者らは、Ｒ−１２
５およびＲ−１１５を含んで成る混合物からＲ−１１５
を除去する方法について研究を重ねた結果、Ｒ−１２５
とＲ−１１５は最低共沸混合物を形成することを見いだ
し、本発明を完成した。この共沸混合物は、Ｒ−１２５
とＲ−１１５を含んで成る混合物からＲ−１１５を除去
する際の蒸留操作の還流として使用することができ、そ
れにより有効な分離が可能となる。Means for Solving the Problems The present inventors have proposed R-12.
5 and R-115 from a mixture comprising
As a result of repeated studies on a method for removing
And R-115 formed the lowest azeotrope, and completed the present invention. This azeotrope is R-125
Can be used as a reflux in a distillation operation to remove R-115 from a mixture comprising R-115 and R-115, thereby enabling efficient separation.
【０００４】従って、第１の要旨において、本発明はＲ
−１２５とＲ−１１５との共沸混合物を提供する。Ｒ−
１２５の沸点は、大気圧下において−４８.５℃であ
り、Ｒ−１１５の沸点は大気圧下において−３８．７℃
である。この共沸混合物の沸点は、大気圧下において、
約−５５℃であり、従って、最低共沸することとなる。
その時の共沸組成は、Ｒ−１２５が約８５モル％、Ｒ−
１１５が約１５モル％である。また、他の圧力、例えば
１０Ｋg／cm2absにおいて、沸点は約１１.５℃であり、
共沸組成は、Ｒ−１２５が約９３モル％、Ｒ−１１５が
約７モル％である。Accordingly, in a first aspect, the present invention provides an R
An azeotrope of -125 and R-115 is provided. R-
The boiling point of 125 is -48.5 ° C at atmospheric pressure, and the boiling point of R-115 is -38.7 ° C at atmospheric pressure.
It is. The boiling point of this azeotrope at atmospheric pressure is
About -55 ° C, and therefore will azeotropize at the lowest.
The azeotropic composition at that time was such that R-125 was about 85 mol%,
115 is about 15 mol%. At another pressure, for example, 10 kg / cm 2 abs, the boiling point is about 11.5 ° C.,
The azeotropic composition is about 93 mol% for R-125 and about 7 mol% for R-115.
【０００５】第２の要旨において、本発明は、Ｒ−１２
５およびＲ−１１５の混合物を蒸留することにより、Ｒ
−１１５をＲ−１２５との共沸混合物として留出させて
除去し、実質的にＲ−１１５を含まないＲ−１２５得る
ことを特徴とする、Ｒ−１２５およびＲ−１１５の混合
物からＲ−１１５を分離する方法を提供する。[0005] In a second aspect, the present invention relates to R-12
5 and R-115 by distillation
-115 is distilled off as an azeotrope with R-125 to obtain R-125 substantially free of R-115, wherein R-125 is obtained from a mixture of R-125 and R-115. 115 is provided.
【０００６】前述のごとく、Ｒ−１２５とＲ−１１５の
２成分系には(最低)共沸混合物が存在する。この共沸混
合物は、本発明者らが初めて見いだした。Ｒ−１２５と
Ｒ−１１５との混合物を例えば大気圧下で蒸留すると、
Ｒ−１２５／Ｒ−１１５のモル比で約８５／１５以上に
Ｒ−１２５を濃縮することはできないことが見いだされ
た。言い替えると、この組成比の液相は平衡状態にある
気相の組成比と同一となる。As mentioned above, the (minimum) azeotrope exists in the binary system of R-125 and R-115. This azeotrope was found for the first time by the present inventors. When a mixture of R-125 and R-115 is distilled, for example, under atmospheric pressure,
It has been found that R-125 cannot be concentrated above about 85/15 at a molar ratio of R-125 / R-115. In other words, the liquid phase having this composition ratio is the same as the composition ratio of the gas phase in an equilibrium state.
【０００７】Ｒ−１２５とＲ−１１５は共沸混合物を形
成することが見いだされているので、Ｒ−１２５および
Ｒ−１１５の混合物中のＲ−１１５の組成が、共沸組成
より小さい場合、Ｒ−１２５とＲ−１１５の共沸混合物
を還流として用いる蒸留操作により、塔頂から共沸組成
物を留出させると共に、塔底からＲ−１１５を実質的に
含まないＲ−１２５を効率的に得ることができる。Since R-125 and R-115 have been found to form an azeotrope, if the composition of R-115 in the mixture of R-125 and R-115 is less than the azeotropic composition, By an distillation operation using an azeotropic mixture of R-125 and R-115 as reflux, an azeotropic composition is distilled from the top of the column, and R-125 substantially free of R-115 is efficiently removed from the bottom of the column. Can be obtained.
【０００８】このような蒸留操作に使用する蒸留装置
は、通常の蒸留に必要な機能を備えていればどのような
ものでも使用可能である。棚段塔や、充填塔などの精留
装置を使用する場合が特に好ましい結果となる。また、
バッチ蒸留または連続蒸留のいずれでも実施可能であ
る。[0008] Any distillation apparatus can be used as long as it has a function necessary for ordinary distillation. Particularly preferable results are obtained when a rectifying device such as a tray column or a packed column is used. Also,
Either batch distillation or continuous distillation can be performed.
【０００９】蒸留の操作条件は、ユーティリティの問
題、要求される分離度などにより種々の態様が可能であ
り、限定的なものではない。蒸留塔の塔頂温度が低く成
り過ぎないことを考慮すると、操作圧力は、特に約１〜
３０Ｋg／cm2abs、より好ましくは、約５〜１５Ｋg／cm
2absとすることが好ましい。この場合、塔頂温度は、そ
れぞれ約−５５〜６０℃、約−１０〜３０℃となる。[0009] The operating conditions of the distillation are not limited, and various modes are possible depending on the problem of the utility and the required degree of separation. Taking into account that the overhead temperature of the distillation column does not become too low, the operating pressure is in particular between about 1 and 1.
30 kg / cm 2 abs, more preferably about 5 to 15 kg / cm
It is preferably 2 abs. In this case, the top temperatures are about -55 to 60C and about -10 to 30C, respectively.
【００１０】本発明は、特に、テトラクロロエチレン
を、触媒の存在下、気相でフッ化水素（ＨＦ）によりフ
ッ素化して得られるＲ−１２５と副生するＲ−１１５を
含む混合物からＲ−１１５を除去するのに有効である。The present invention particularly relates to a process for producing R-115 from a mixture containing R-125 obtained by fluorinating tetrachloroethylene in the gas phase with hydrogen fluoride (HF) in the presence of a catalyst and R-115 by-produced. It is effective to remove.
【００１１】次に、本発明の最も好ましい実施態様を以
下に示す。本発明の方法に用いられる分離装置の一例を
フローシートにて図１に示す。通常、前記の反応では生
成物を気相で抜き出す。得られる混合物中にはＲ−１２
５、１,１,１,２−テトラフルオロクロロエタン（Ｒ−
１２４）、１,１,１−トリフルオロジクロロエタン（Ｒ
−１２３）、ＨＦおよび塩化水素の他に少量のＲ−１１
５等の有機物が含まれている。この反応生成物である混
合物から塩化水素及びＨＦを常套の方法、例えば水洗及
び分液、共沸蒸留により除去した、Ｒ−１２５、Ｒ−１
２４、Ｒ−１２３および少量のＲ−１１５等の有機物を
含む混合物１は、蒸留装置２に導かれる。Next, the most preferred embodiments of the present invention will be described below. One example of the separation apparatus used in the method of the present invention is shown in FIG. 1 as a flow sheet. Usually, in the above-mentioned reaction, a product is extracted in a gas phase. R-12 is contained in the resulting mixture.
5,1,1,1,1,2-tetrafluorochloroethane (R-
124) 1,1,1-trifluorodichloroethane (R
-123), a small amount of R-11 in addition to HF and hydrogen chloride.
5th grade organic matter. Hydrogen chloride and HF were removed from the reaction product mixture by a conventional method, for example, washing with water, separation and azeotropic distillation.
The mixture 1 containing an organic substance such as 24, R-123 and a small amount of R-115 is led to the distillation apparatus 2.
【００１２】この蒸留装置２において、塔頂よりＲ−１
２５と共沸するＲ−１１５の一部を留出物３として取り
出し、一部を還流４として蒸留装置の塔頂に戻す。蒸留
装置１の塔底部からは実質的にＲ−１１５を含まないＲ
−１２５、Ｒ−１２４、Ｒ−１２３および沸点がＲ−１
２５より高い少量の有機物の混合物を缶出物５として抜
き出す。このようにして、前記混合物中より、Ｒ−１１
５を効率的に除去することが出来る。このような操作
は、バッチ式に行うことも可能であるが、連続操作によ
り行うことが好ましい。In this distillation apparatus 2, R-1
A part of R-115 azeotroping with 25 is taken out as distillate 3, and a part is taken as reflux 4 and returned to the top of the distillation apparatus. From the bottom of the distillation apparatus 1, R containing substantially no R-115
-125, R-124, R-123 and a boiling point of R-1
A small amount of the organic mixture higher than 25 is withdrawn as bottom product 5. In this way, from the mixture, R-11
5 can be efficiently removed. Such an operation can be performed in a batch manner, but is preferably performed by a continuous operation.
【００１３】[0013]
【実施例】以下、実施例により本発明を詳細に説明す
る。 実施例１ 真空ジャケット付きオルダーショウ蒸留塔(直径:２５m
m、１５段)の塔底のフラスコにＲ−１２５を２４０g(２
mol)およびＲ−１１５を３０.９g(０.２mol)仕込み、大
気圧下、全還流で蒸留を開始した。塔頂温度が約−５５
℃となった時に留出液をサンプリングした。このサンプ
ルを分析すると、Ｒ−１２５／Ｒ−１１５のモル比は約
８５／１５であった。The present invention will be described below in detail with reference to examples. Example 1 Aldershaw distillation column equipped with a vacuum jacket (diameter: 25 m
240g of R-125 (2
mol) and 30.9 g (0.2 mol) of R-115, and distillation was started at atmospheric pressure and total reflux. The top temperature is about -55
The distillate was sampled when the temperature reached ° C. When this sample was analyzed, the molar ratio of R-125 / R-115 was about 85/15.
【００１４】この分析結果から、Ｒ−１２５より高い沸
点を有するＲ−１１５(Ｒ−１２５の常圧沸点−４８.５
℃＜Ｒ−１１５の常圧沸点−３８.７℃)が塔頂部に濃縮
されることが明らかとなり、Ｒ−１２５とＲ−１１５は
最低共沸混合物を形成することが確認された。From the results of this analysis, it was found that R-115 having a boiling point higher than that of R-125 (normal pressure boiling point of R-125-48.5)
C. <R-115 normal pressure boiling point −38.7 ° C.) was found to be concentrated at the top of the column, and it was confirmed that R-125 and R-115 form the lowest azeotrope.
【００１５】実施例２ 実施例１と同じ装置を用いて同様に、Ｒ−１２５を３６
０g(３mol)およびＲ−１１５を１５.５g(０.１mol)仕込
み、大気圧下で全還流にて蒸留塔を安定させた。安定
後、塔頂からの流出液を徐々に抜き出して行くと、塔頂
温度が徐々に上昇し、塔頂温度がスチル温度（−５５
℃）と同じになった時に加熱を停止した。塔頂から抜き
出した液量は、約２１０gとなり、スチルからはＲ−１
１５約３０ppmを含むＲ−１２５約１５０gを得た。Example 2 Using the same apparatus as in Example 1, R-125 was
0 g (3 mol) and 15.5 g (0.1 mol) of R-115 were charged, and the distillation column was stabilized under atmospheric pressure and total reflux. After the stabilization, the effluent from the top is gradually extracted, and the top temperature gradually increases, and the top temperature becomes the still temperature (−55 ° C.).
C.), the heating was stopped. The amount of liquid withdrawn from the top was about 210 g, and R-1
About 150 g of R-125 containing 15 about 30 ppm were obtained.
【００１６】この結果から、Ｒ−１２５およびＲ−１１
５の混合物を蒸留して、Ｒ−１２５およびＲ−１１５の
共沸現象を利用することにより、Ｒ−１２５およびＲ−
１１５の混合物からＲ−１１５を分離できることが判
る。From the results, R-125 and R-11
By distilling the mixture of 5 and utilizing the azeotropic phenomenon of R-125 and R-115, R-125 and R-
It can be seen that R-115 can be separated from the 115 mixture.
【図１】 本発明を用いた、ペンタフルオロクロロエタ
ンの除去装置の一例のフローシートである。FIG. 1 is a flow sheet of an example of an apparatus for removing pentafluorochloroethane using the present invention.
１…仕込液、２…蒸留装置、３…留出物、４…還流、５
…缶出物。DESCRIPTION OF SYMBOLS 1 ... Charge liquid, 2 ... Distillation apparatus, 3 ... Distillate, 4 ... Reflux, 5
... cans.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 米国特許3505233（ＵＳ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 19/08 C07C 19/12 C07C 17/383 ＣＡ（ＳＴＮ) ＣＡＯＬＤ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── (5) References US Patent 3,505,233 (US, A) (58) Fields investigated (Int. Cl. 7 , DB name) C07C 19/08 C07C 19/12 C07C 17/383 CA ( STN) CAOLD (STN) REGISTRY (STN)
Claims (3)
クロロエタンとの共沸混合物。An azeotropic mixture of pentafluoroethane and pentafluorochloroethane.
ペンタフルオロクロロエタンを含んで成る混合物を蒸留
し、ペンタフルオロエタンとペンタフルオロクロロエタ
ンとの共沸混合物を留出させることを特徴とする、少な
くともペンタフルオロエタンおよびペンタフルオロクロ
ロエタンを含んで成る混合物からペンタフルオロクロロ
エタンを分離する方法。2. A method comprising distilling a mixture comprising at least pentafluoroethane and pentafluorochloroethane to distill an azeotrope of pentafluoroethane and pentafluorochloroethane. A method for separating pentafluorochloroethane from a mixture comprising fluorochloroethane.
て蒸留することを特徴とする請求項２記載の方法。3. The process according to claim 2, wherein the distillation is carried out at an operating pressure of 1 to 30 kg / cm 2 abs.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12460892A JP3182869B2 (en) | 1992-05-18 | 1992-05-18 | Azeotropic mixture of pentafluoroethane and pentafluorochloroethane and method for separating pentafluorochloroethane |
| PCT/JP1993/000637 WO1993023355A1 (en) | 1992-05-18 | 1993-05-14 | Azeotropic mixture of pentafluoroethane with pentafluorochloroethane and separation of pentafluorochloroethane |
| AU40880/93A AU4088093A (en) | 1992-05-18 | 1993-05-14 | Azeotropic mixture of pentafluoroethane with pentafluorochloroethane and separation of pentafluorochloroethane |
| CN 93107029 CN1085536A (en) | 1992-05-18 | 1993-05-18 | The separation method of pentafluoride ethane and five fluorine chloric ethane azeotropic mixtures and five fluorine chloric ethanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12460892A JP3182869B2 (en) | 1992-05-18 | 1992-05-18 | Azeotropic mixture of pentafluoroethane and pentafluorochloroethane and method for separating pentafluorochloroethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05320077A JPH05320077A (en) | 1993-12-03 |
| JP3182869B2 true JP3182869B2 (en) | 2001-07-03 |
Family
ID=14889646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12460892A Expired - Fee Related JP3182869B2 (en) | 1992-05-18 | 1992-05-18 | Azeotropic mixture of pentafluoroethane and pentafluorochloroethane and method for separating pentafluorochloroethane |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP3182869B2 (en) |
| CN (1) | CN1085536A (en) |
| AU (1) | AU4088093A (en) |
| WO (1) | WO1993023355A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5346595A (en) * | 1993-02-23 | 1994-09-13 | Alliedsignal Inc. | Process for the purification of a pentafluoroethane azeotrope |
| ATE177417T1 (en) * | 1993-04-30 | 1999-03-15 | Du Pont | AZEOTROPIC AND AZEOTROPICAL COMPOSITIONS AND METHODS FOR SEPARATING HCL AND HALOHYDROCARBONS |
| US5421964A (en) * | 1993-04-30 | 1995-06-06 | E. I. Du Pont De Nemours And Company | Process for separating HCl and halocarbons |
| AU684757B2 (en) * | 1993-05-25 | 1998-01-08 | Showa Denko Kabushiki Kaisha | Purification process of pentafluoroethane |
| DE69513152T2 (en) * | 1994-02-07 | 2000-06-21 | E.I. Du Pont De Nemours And Co., Wilmington | METHOD FOR SEPARATING PENTAFLUORETHANE FROM A MIXTURE CONTAINING HALOGENED HYDROCARBONS AND CHLORPENTAFLUORETHANE |
| US5718807A (en) * | 1994-09-20 | 1998-02-17 | E. I. Du Pont De Nemours And Company | Purification process for hexafluoroethane products |
| US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
| JP2003055277A (en) * | 2001-08-16 | 2003-02-26 | Showa Denko Kk | Method for producing hexafluoroethane and use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3505233A (en) * | 1968-11-12 | 1970-04-07 | Union Carbide Corp | Chloropentafluoroethane-pentafluoroethane azeotropic compositions |
| JPH02197634A (en) * | 1989-01-25 | 1990-08-06 | Toto Ltd | Privates cleaner |
| US5087329A (en) * | 1991-05-16 | 1992-02-11 | E. I. Du Pont De Nemours And Company | Process for separating pentafluoroethane from a mixture of halogenated hydrocarbons containing chloropentafluoroethane |
-
1992
- 1992-05-18 JP JP12460892A patent/JP3182869B2/en not_active Expired - Fee Related
-
1993
- 1993-05-14 AU AU40880/93A patent/AU4088093A/en not_active Withdrawn
- 1993-05-14 WO PCT/JP1993/000637 patent/WO1993023355A1/en active Application Filing
- 1993-05-18 CN CN 93107029 patent/CN1085536A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU4088093A (en) | 1993-12-13 |
| JPH05320077A (en) | 1993-12-03 |
| WO1993023355A1 (en) | 1993-11-25 |
| CN1085536A (en) | 1994-04-20 |
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