WO1993023355A1 - Azeotropic mixture of pentafluoroethane with pentafluorochloroethane and separation of pentafluorochloroethane - Google Patents

Azeotropic mixture of pentafluoroethane with pentafluorochloroethane and separation of pentafluorochloroethane Download PDF

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Publication number
WO1993023355A1
WO1993023355A1 PCT/JP1993/000637 JP9300637W WO9323355A1 WO 1993023355 A1 WO1993023355 A1 WO 1993023355A1 JP 9300637 W JP9300637 W JP 9300637W WO 9323355 A1 WO9323355 A1 WO 9323355A1
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Prior art keywords
pentafluorochloroethane
mixture
distillation
azeotrope
pentafluoroethane
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PCT/JP1993/000637
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French (fr)
Japanese (ja)
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Takehide Tsuda
Satoshi Komatsu
Takeo Matsumoto
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Daikin Industries, Ltd.
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    • 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

Definitions

  • the present invention relates to an azeotrope of pentafluoroethane (hereinafter, referred to as R-125) and pentafluorochloroethane (hereinafter, referred to as R-115), and R A method for separating R-115 from a mixture comprising R-125 and R-115.
  • R-125 pentafluoroethane
  • R-115 pentafluorochloroethane
  • R-125 is receiving attention as an alternative refrigerant to chlorodifluoromethane.
  • R-125 is usually produced by reacting carbon chloride such as tetrachloroethylene with hydrogen fluoride (HF). At this time, R-115, a by-product, must be removed because it is a substance that destroys ozone. However, to date, no method for separating R-115 from a mixture comprising R-125 and R-115 has been described in any literature.
  • carbon chloride such as tetrachloroethylene
  • HF hydrogen fluoride
  • the present inventors have studied a method for removing R-115 from a mixture comprising R-125 and R-115, and have found that R-125 and R-115 Found the formation of the lowest azeotrope, and completed the present invention.
  • This azeotrope can be used as a reflux in a distillation operation to remove R-115 from a mixture comprising R-125 and R-115, thereby providing an effective Separation becomes possible.
  • the present invention provides an azeotrope of R-125 and R-115.
  • the boiling point of R-125 is 148.5 ° C under atmospheric pressure
  • the boiling point of R-115 is 138.7 ° C under atmospheric pressure.
  • the boiling point of this azeotrope is about -55 ° C under atmospheric pressure, and therefore, it will azeotropize at the lowest.
  • the azeotropic composition at that time is about 85 mol% of R-125 and about 5 mol% of R-115.
  • the starting point is about 11.5 ° C and the azeotropic composition is about 93 mol% for R-125 and about 7 mol% for R-115.
  • the present invention provides a method for distilling a mixture of R-125 and R-115 to distill and remove R-115 as an azeotrope with R-125.
  • FIG. 1 is a flow sheet of an example of an apparatus for removing pentafluorochloroethane using the present invention.
  • reference number 1 indicates the feed liquid comprising R-125 and R-115
  • 2 indicates the distillation apparatus
  • 3 indicates the distillate
  • 4 indicates the reflux
  • 5 indicates the bottom product .
  • the (minimum) azeotrope exists in the binary system of R-125 and R-115. This azeotrope has been found for the first time by the present inventors.
  • the composition of R—115 in the mixture of R—125 and R—115 is If the azeotropic composition is smaller than the azeotropic composition, the azeotropic composition is distilled from the top of the column by distillation using an azeotropic mixture of R-125 and R-115 as reflux, and R- It is possible to efficiently obtain R—125, which is substantially free of 115.
  • the composition of R—11 ⁇ in a mixture comprising R—125 and R—115 is greater than the azeotropic composition, the azeotrope of R—125 and scale-115 By performing a distillation operation using the mixture as reflux, an azeotropic composition can be distilled off from the top of the column and R-115 substantially free of R-125 can be efficiently obtained from the bottom of the column .
  • a mixture comprising R-125 and R-115 is a mixture of R-125 and R-115 in a distillation operation, even if other components are simultaneously present.
  • An azeotropic composition is formed. That is, even when components other than R-115 and R-125 coexist, R-125 and R-115 can be separated by the present invention.
  • the other coexisting components are preferentially contained in either the distillate side or the bottom side due to the relative height relationship between the azeotropic temperature of the azeotropic composition and the boiling point of the coexisting components. .
  • Any distillation apparatus can be used as long as it has the functions necessary for ordinary distillation. Particularly preferable results are obtained when a rectifying device such as a tray column or a packed column is used. In addition, it can be carried out with or without batch distillation or continuous distillation.
  • the operation conditions of the distillation are not limited and various modes are possible depending on the problem of the utility, the required degree of separation, and the like.
  • the top temperature of the distillation column Considering that it does not become too low, the operating pressure is preferably about 1 to 30 KgZcni 2 abs., More preferably about 5 to 15 KgZcni 2 abs. In this case, the top temperature is about 1 55-60 ° C and about 1 10-30 ° C, respectively.
  • the present invention is to remove R-115 from a mixture containing R-125 produced as a result of fluorination of tetrachloroethylene in the gas phase with hydrogen fluoride (HF) in the presence of a catalyst and R-115 by-produced. It is effective for
  • R-125 1,1,1,2-tetrafluorochloroethane (R-124), 1: U1-Trifluorodichloroethane (R-123)
  • R-115 contains small amounts of organic substances such as R-115 in addition to HF and hydrogen chloride.
  • Hydrogen chloride and HF were removed from the reaction product mixture by conventional methods such as washing with water, separation and azeotropic distillation, such as R-125.
  • R-124, R-123 and a small amount of R-115 The mixture 1 containing organic matter is led to the distillation apparatus 2.
  • R-115 is a by-product whose composition is smaller than the azeotropic composition in relation to R-125.

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

Abstract

A method of efficiently separating pentafluorochloroethane from a mixture containing the same and pentafluoroethane, which comprises distilling said mixture to thereby evaporate an azeotropic mixture composed of both the halogenated ethanes.

Description

明 細 書 ペンタフルォロエタンとペンタフルォロクロロェタンとの 共沸混合物およびペンタフルォロクロロエタンの分離方法  Specification An azeotropic mixture of pentafluoroethane and pentafluorochloroethane and a method for separating pentafluorochloroethane
【技術分野】 【Technical field】
本発明は、 ペンタフルォロェタン（以下、 R— 1 2 5と称する。 ）とペン タフルォロクロロェタン (以下、 R— 1 1 5と称す。 ）の共沸混合物、 およ び、 R— 1 2 5および R— 1 1 5を含んで成る混合物から R— 1 1 5を分 離する方法に関する。  The present invention relates to an azeotrope of pentafluoroethane (hereinafter, referred to as R-125) and pentafluorochloroethane (hereinafter, referred to as R-115), and R A method for separating R-115 from a mixture comprising R-125 and R-115.
R— 1 2 5は、 クロロジフルォロメタンの代替冷媒として着目されてい る 0  R-125 is receiving attention as an alternative refrigerant to chlorodifluoromethane. 0
【背景技術】  [Background Art]
R— 1 2 5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 （H F) 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— 1 1 5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— 1 2 5および R— 1 1 5を含んで成る混合物から R— 1 1 5を分離する方法はいかなる文献にも記載されていない。  R-125 is usually produced by reacting carbon chloride such as tetrachloroethylene with hydrogen fluoride (HF). At this time, R-115, a by-product, must be removed because it is a substance that destroys ozone. However, to date, no method for separating R-115 from a mixture comprising R-125 and R-115 has been described in any literature.
【発明の開示】  DISCLOSURE OF THE INVENTION
本発明者らは、 R— 1 2 5および R— 1 1 5を含んで成る混合物から R 一 1 1 5を除去する方法について研究を重ねた結果、 R— 1 2 5と R— 1 1 5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— 1 2 5と R— 1 1 5を含んで成る混合物から R— 1 1 5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。 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、 大気圧下において一 48.5 °Cであり、 R— 115の沸点は大気圧下において一 38.7°Cである。 こ の共沸混合物の沸点は、大気圧下において、 約— 55°C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 5モル％である。 また、 他の圧力、 例えば lOKg Zcm2absにおいて、 拂点は約 11.5°C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。 The present inventors have studied a method for removing R-115 from a mixture comprising R-125 and R-115, and have found that R-125 and R-115 Found the formation of the lowest azeotrope, and completed the present invention. This azeotrope can be used as a reflux in a distillation operation to remove R-115 from a mixture comprising R-125 and R-115, thereby providing an effective Separation becomes possible. Accordingly, in a first aspect, the present invention provides an azeotrope of R-125 and R-115. The boiling point of R-125 is 148.5 ° C under atmospheric pressure, and the boiling point of R-115 is 138.7 ° C under atmospheric pressure. The boiling point of this azeotrope is about -55 ° C under atmospheric pressure, and therefore, it will azeotropize at the lowest. The azeotropic composition at that time is about 85 mol% of R-125 and about 5 mol% of R-115. At other pressures, such as lOKg Zcm 2 abs, the starting point is about 11.5 ° C and the azeotropic composition is about 93 mol% for R-125 and about 7 mol% for R-115.
第 2の要旨において、 本発明は、 R— 125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 徵とする、 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。  In a second aspect, the present invention provides a method for distilling a mixture of R-125 and R-115 to distill and remove R-115 as an azeotrope with R-125. Provided is a method for separating R-115 from a mixture of R-125 and R-115, characterized by obtaining R-125 containing no 115.
【図面の簡単な説明】  [Brief description of the drawings]
図 1は、 本発明を用いた、 ペンタフルォロクロロェタンの除去装置の一 例のフローシートである。- 図 1において、 引用番号 1は R— 125および R— 115を含んで成る 仕込液を、 2は蒸留装置を、 3は留出物を、 4は還流を、 5は缶出物を示 す。  FIG. 1 is a flow sheet of an example of an apparatus for removing pentafluorochloroethane using the present invention. -In Fig. 1, reference number 1 indicates the feed liquid comprising R-125 and R-115, 2 indicates the distillation apparatus, 3 indicates the distillate, 4 indicates the reflux, and 5 indicates the bottom product .
【発明の詳細な説明】  DETAILED DESCRIPTION OF THE INVENTION
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。  As mentioned above, the (minimum) azeotrope exists in the binary system of R-125 and R-115. This azeotrope has been found for the first time by the present inventors.
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 一 125ZR— 115のモル比で約 85Z15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  For example, when a mixture of R-125 and R-115 was distilled under atmospheric pressure, it was found that R-125 could not be concentrated to a molar ratio of R-125ZR-115 of about 85Z15 or more. In other words, the liquid phase of this composition ratio
-9- は平衡状態にある気相の組成比と同一となる。 -9- Is the same as the composition ratio of the gas phase in the equilibrium state.
R— 1 2 5と R— 1 1 5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— 1 2 5および R— 1 1 5の混合物中の R— 1 1 5の組成が、 共沸組成より小さい場合、 R— 1 2 5と R— 1 1 5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— 1 1 5を実質的に含まない R— 1 2 5を効率的に得ることがで ^る。  Since R—125 and R—115 have been found to form an azeotrope, the composition of R—115 in the mixture of R—125 and R—115 is If the azeotropic composition is smaller than the azeotropic composition, the azeotropic composition is distilled from the top of the column by distillation using an azeotropic mixture of R-125 and R-115 as reflux, and R- It is possible to efficiently obtain R—125, which is substantially free of 115.
逆に、 R— 1 2 5および R— 1 1 5を含んで成る混合物中の R— 1 1 δ の組成が共沸組成より大きい場合、 R— 1 2 5と尺ー 1 1 5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— 1 2 5を実質的に含まない R— 1 1 5を効率的に得る こともできる。  Conversely, if the composition of R—11δ in a mixture comprising R—125 and R—115 is greater than the azeotropic composition, the azeotrope of R—125 and scale-115 By performing a distillation operation using the mixture as reflux, an azeotropic composition can be distilled off from the top of the column and R-115 substantially free of R-125 can be efficiently obtained from the bottom of the column .
本発明において、 R— 1 2 5および R— 1 1 5を含んで成る混合物は、 他の成分が同時に存在する場合であっても、 蒸留操作において R— 1 2 5 および R— 1 1 5の共沸組成物が形成される。 即ち、 R— 1 1 5および R 一 1 2 5以外の成分が共存している場合であっても、 本発明により、 R— 1 2 5と R— 1 1 5とを分離することができる。 この場合、 他の共存成分 は、 共沸組成物の共沸温度と共存成分の沸点との相対的な高低関係により、 留出側または缶出側のいずれかに優先的に含まれることになる。  In the present invention, a mixture comprising R-125 and R-115 is a mixture of R-125 and R-115 in a distillation operation, even if other components are simultaneously present. An azeotropic composition is formed. That is, even when components other than R-115 and R-125 coexist, R-125 and R-115 can be separated by the present invention. In this case, the other coexisting components are preferentially contained in either the distillate side or the bottom side due to the relative height relationship between the azeotropic temperature of the azeotropic composition and the boiling point of the coexisting components. .
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 または連続蒸留のし、ずれでも実施可能である。  Any distillation apparatus can be used as long as it has the functions necessary for ordinary distillation. Particularly preferable results are obtained when a rectifying device such as a tray column or a packed column is used. In addition, it can be carried out with or without batch distillation or continuous distillation.
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 l〜30KgZc ni2abs. より好ましくは、 約 5〜15KgZcni2absとすることが好ましい。 この場合、 塔頂温度は、それぞれ約一 55〜60°C、 約一 10〜30°Cと る。 The operation conditions of the distillation are not limited and various modes are possible depending on the problem of the utility, the required degree of separation, and the like. The top temperature of the distillation column Considering that it does not become too low, the operating pressure is preferably about 1 to 30 KgZcni 2 abs., More preferably about 5 to 15 KgZcni 2 abs. In this case, the top temperature is about 1 55-60 ° C and about 1 10-30 ° C, respectively.
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— 1 15を含む混合物から R— 115を除去するのに有効である。  In particular, the present invention is to remove R-115 from a mixture containing R-125 produced as a result of fluorination of tetrachloroethylene in the gas phase with hydrogen fluoride (HF) in the presence of a catalyst and R-115 by-produced. It is effective for
【発明を実施するための好ましい態様】  BEST MODE FOR CARRYING OUT THE INVENTION
次に、 本発明の最も好ましい実施態様を以下に示す。  Next, the most preferred embodiments of the present invention will be described below.
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— 125、 1， 1， 1， 2—テトラフルォロクロロェタン （R— 12 4)、 1，： U 1—トリフルォロジクロロェタン （R— 123)、 HFおよ び塩化水素の他に少量の R— 115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 H F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—124、 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。 この場合、 R— 115は副生成物であり、 その組成は、 R— 125と の相対的な関係において、 共沸組成より小さい。  One example of the separation apparatus used in the method of the present invention is shown in a flow sheet in FIG. Usually, in the above reaction, the product is withdrawn in the gas phase. In the resulting mixture, R-125, 1,1,1,2-tetrafluorochloroethane (R-124), 1: U1-Trifluorodichloroethane (R-123), It contains small amounts of organic substances such as R-115 in addition to HF and hydrogen chloride. Hydrogen chloride and HF were removed from the reaction product mixture by conventional methods such as washing with water, separation and azeotropic distillation, such as R-125. R-124, R-123 and a small amount of R-115. The mixture 1 containing organic matter is led to the distillation apparatus 2. In this case, R-115 is a by-product whose composition is smaller than the azeotropic composition in relation to R-125.
この蒸留装置 2において、 塔頂より R— 12 δと共沸する R— 115の —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— 125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— 115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, a part of R-115, which azeotropes with R-12 δ, is taken out as distillate 3 from the top of the column as a distillate 3, and a part thereof is returned to the top of the distillation apparatus as reflux 4. From the bottom of the distillation apparatus 1, a mixture of R-125, R-124, R-123 and a small amount of organic substances having a boiling point higher than that of R-125, which is substantially free of R-115, is withdrawn as bottom product 5. Thus, R-115 can be efficiently removed from the mixture. Such an operation can be performed in a batch manner, but is preferably performed by a continuous operation.
【実施例】  【Example】
以下、 実施例により本発明を詳細に説明する。  Hereinafter, the present invention will be described in detail with reference to examples.
実施例 1  Example 1
真空ジャケッ ト付きオルダ一ショウ蒸留塔（直径： 25mni、 15段）の塔 底のフラスコに R— 125を 240g(2mol)および R— 115を 30.9 g (0.2mol)仕込み、 大気圧下、 全還流で蒸留を開始した。 塔頂温度が約一 δ 5°C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ノ R— 115のモル比は約 85/15であった。  240 g (2 mol) of R-125 and 30.9 g (0.2 mol) of R-125 were charged into the bottom flask of an Oldasha distillation column with a vacuum jacket (diameter: 25 mni, 15 plates), and refluxed under atmospheric pressure. Started the distillation. The distillate was sampled when the temperature at the top of the column was about 1 δ5 ° C. When this sample was analyzed, the molar ratio of R-125 to R-115 was about 85/15.
この分析結果から、 R— 125より高い沸点を有する R— 115(R— 125の常圧沸点一 48.5°C<R— 115の常圧沸点一 38.7°C)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 this analysis result, it can be concluded that R-115 having a boiling point higher than that of R-125 (normal boiling point of R-125-48.5 ° C <atmospheric pressure boiling point of R-115-38.7 ° C) is concentrated at the top of the column. It became clear that R-125 and R-115 formed the lowest azeotrope.
実施例 2  Example 2
実施例 1と同じ装置を用いて同様に、 R— 125を 360g(3mol)およ び R— 115を 15.5 g( 0.1 mol)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、 塔頂からの留出液を徐々に系外に抜き出して行く と、 塔頂温度が徐々に上昇し、 塔頂温度がスチル温度 （一 48. δ0Ο 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 210 gとなり、 スチルからは R— 115約 3 Oppmを含む R— 125約 150g を得た。 Similarly, using the same apparatus as in Example 1, 360 g (3 mol) of R-125 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 stabilization, the go withdrawn gradually out of the system a distillate from the column top, when raised top temperature gradually, top temperature became equal to the still temperature (one 48. [delta] 0 Omicron heating The amount of liquid withdrawn from the top of the column was about 210 g, and about 150 g of R-125 containing about 3 Oppm of R-115 was obtained from the still.
この結果から、 R— 125および R— 115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 this result, it is possible to distill the mixture of R-125 and R-115 from the mixture of R-125 and R-115 by utilizing the azeotropic phenomenon of R-125 and R-115 by distilling the mixture of R-125 and R-115. It can be seen that they can be separated.
-0- -0-

Claims

請 求 の 範 囲 The scope of the claims
1. ペンタフ レオロェタンとペンタフルォロクロロェタンとの共沸混合 物 o 1. An azeotrope of pentafluoroene and pentafluorochloroethane o
2. 少なくともペンタフルォロェタンおよびペンタフルォロクロ口エタ ンを含んで成る混合物を蒸留し、 ペンタフルォロェタンとペンタフルォロ クロロェタンとの共沸混合物を留出させることを特徵とする、 少なくとも ペンタフルォロエタンおよびペンタフルォロクロロェタンを含んで成る混 合物からペンタフルォロクロロェタンを分離する方法。  2. A method comprising distilling a mixture comprising at least pentafluoroethane and pentafluorochloromethane to distill an azeotrope of pentafluorochloroethane and pentafluorochloroethane, comprising: A method for separating pentafluorochloroethane from a mixture comprising fluoroethane and pentafluorochloroethane.
3. 1〜3 0 KgZcm2absの操作圧力において蒸留することを特徵とす る請求項 2記載の方法ひ 3. The process according to claim 2, characterized in that the distillation is carried out at an operating pressure of 1 to 30 KgZcm 2 abs.
PCT/JP1993/000637 1992-05-18 1993-05-14 Azeotropic mixture of pentafluoroethane with pentafluorochloroethane and separation of pentafluorochloroethane WO1993023355A1 (en)

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WO1994019301A1 (en) * 1993-02-23 1994-09-01 Alliedsignal Inc. Purification of a component of a binary azeotrope
US5421964A (en) * 1993-04-30 1995-06-06 E. I. Du Pont De Nemours And Company Process for separating HCl and halocarbons
US5665266A (en) * 1993-04-30 1997-09-09 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions with HCL and halocarbon
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
US6179967B1 (en) * 1993-05-25 2001-01-30 Showa Denko K.K. Purification process of pentrafluoroethane

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JP2003055277A (en) * 2001-08-16 2003-02-26 Showa Denko Kk Method for producing hexafluoroethane and use thereof

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Cited By (8)

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WO1994019301A1 (en) * 1993-02-23 1994-09-01 Alliedsignal Inc. Purification of a component of a binary azeotrope
US5421964A (en) * 1993-04-30 1995-06-06 E. I. Du Pont De Nemours And Company Process for separating HCl and halocarbons
US5665266A (en) * 1993-04-30 1997-09-09 E. I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions with HCL and halocarbon
EP0819669A1 (en) * 1993-04-30 1998-01-21 E.I. Du Pont De Nemours And Company Azeotropic and azeotrope-like compositions and a process for separating HC1 and halocarbons
US5772852A (en) * 1993-04-30 1998-06-30 E. I. Du Pont De Nemours And Company Separating HCI and halocarbons
US6179967B1 (en) * 1993-05-25 2001-01-30 Showa Denko K.K. Purification process of pentrafluoroethane
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

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