JPH06157366A - Method for separating high-boiling halogenated hydrocarbon and hydrogen fluoride - Google Patents
Method for separating high-boiling halogenated hydrocarbon and hydrogen fluorideInfo
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- JPH06157366A JPH06157366A JP4311812A JP31181292A JPH06157366A JP H06157366 A JPH06157366 A JP H06157366A JP 4311812 A JP4311812 A JP 4311812A JP 31181292 A JP31181292 A JP 31181292A JP H06157366 A JPH06157366 A JP H06157366A
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- halogenated hydrocarbon
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Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は高沸点ハロゲン化炭化水
素とフッ化水素の分離方法に関し、詳しくは１,１,１−
トリクロロエタンをフッ化水素と反応させて、１,１−
ジクロロ−１−フルオロエタン(以下、１４１bと略)と
１−クロロ−１,１−ジフルオロエタン(１４２b)を製造
する場合に副生する比較的沸点の高いハロゲン化炭化水
素とフッ化水素とを分離する方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for separating high-boiling halogenated hydrocarbons and hydrogen fluoride, more specifically 1,1,1-
Reacting trichloroethane with hydrogen fluoride to give 1,1-
Separation of halogenated hydrocarbons having a relatively high boiling point and hydrogen fluoride, which are by-products when producing dichloro-1-fluoroethane (hereinafter abbreviated as 141b) and 1-chloro-1,1-difluoroethane (142b) On how to do.
【０００２】[0002]
【従来の技術】１４１bは現在フォーム発泡剤として使
用されているトリクロロフルオロメタンの代替化合物で
あり、発泡剤のみならず、油脂、フラックス等の除去用
洗浄材あるいはドライクリーニング用溶剤としても有用
である。また、１４２bは発泡剤あるいは高分子材料の
原料モノマーとして有用である。１４１b、１４２bは
１,１,１−トリクロロエタン(以下、１４０aと略す)を
過剰のフッ化水素と反応させることにより製造される。
この反応では１４１b、１４２bの外に塩化水素のような
比較的沸点の低い化合物、さらには、ＣＦ3ＣＨ2ＣＦ2
ＣＨ3あるいは塩化ビニリデンのオリゴマーあるいはそ
のフッ素化物の如き、比較的沸点の高いハロゲン化炭化
水素類が副生される。2. Description of the Related Art 141b is an alternative compound of trichlorofluoromethane currently used as a foam blowing agent, and is useful not only as a foaming agent but also as a cleaning material for removing fats and oils, fluxes, etc. or a solvent for dry cleaning. . Further, 142b is useful as a foaming agent or a raw material monomer for a polymer material. 141b and 142b are produced by reacting 1,1,1-trichloroethane (hereinafter abbreviated as 140a) with an excess of hydrogen fluoride.
In this reaction, in addition to 141b and 142b, compounds having a relatively low boiling point such as hydrogen chloride, and further CF 3 CH 2 CF 2
Halogenated hydrocarbons having a relatively high boiling point such as CH 3 or vinylidene chloride oligomers or fluorinated products thereof are by-produced.
【０００３】反応混合物を蒸留するとフッ化水素の一
部、１４１b、１４２b、塩化水素等、比較的沸点の低い
副生物が先ず留去され、フッ化水素の残りと比較的沸点
の高いハロゲン化炭化水素副生物が残存する。該ハロゲ
ン化炭化水素類を除去するためにそのまま蒸留を継続し
ても、それらハロゲン化炭化水素類の多くはフッ化水素
と共沸物を形成するため、フッ化水素と当該副生物を効
果的に分離することは困難である。特開昭５８−２１７
４０３号公報には、１４０aとフッ化水素を反応させて
主として１４２bを製造する場合における、高沸点副生
成物とフッ化水素の分離方法が開示されているが、１４
０aとフッ化水素から主として１４１bを製造する場合に
適用すると、高沸点副生物が目的物である１４１bに混
入し、その分離が困難であるので適当ではない。When the reaction mixture is distilled, a part of hydrogen fluoride, 141b, 142b, by-products having a relatively low boiling point such as hydrogen chloride are first distilled off, and the remainder of hydrogen fluoride and halogenated carbonization having a relatively high boiling point. Hydrogen by-products remain. Even if distillation is continued as it is in order to remove the halogenated hydrocarbons, most of these halogenated hydrocarbons form an azeotrope with hydrogen fluoride, so that hydrogen fluoride and the by-product are effective. Difficult to separate into. JP-A-58-217
Japanese Patent No. 403 discloses a method of separating a high-boiling-point by-product from hydrogen fluoride in the case of mainly producing 142b by reacting 140a with hydrogen fluoride.
When it is mainly applied to the production of 141b from 0a and hydrogen fluoride, the high-boiling by-product is mixed with 141b, which is the target, and its separation is difficult, which is not suitable.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、１４０aを
過剰のフッ化水素と反応させて、主として１４１bを製
造する場合に副生する、比較的高沸点のハロゲン化炭化
水素類をフッ化水素と効率的に分離し、分離されたフッ
化水素の再使用を可能にし、同時に該副生物の１４１b
への混入を阻止せんとするものである。DISCLOSURE OF THE INVENTION According to the present invention, a halogenated hydrocarbon having a relatively high boiling point, which is a by-product when mainly producing 141b by reacting 140a with an excess of hydrogen fluoride, is converted into hydrogen fluoride. And the separated hydrogen fluoride can be reused, and at the same time 141b of the by-product
It is intended to prevent the mixture into the.
【０００５】[0005]
【課題を解決するための手段】本発明者は、上記課題を
解決するための鋭意検討を行った。その結果、比較的高
沸点のハロゲン化炭化水素類とフッ化水素の混合物に１
４１bを加えて蒸留を行えば、フッ化水素は１４１bと共
沸するためそれらの混合物として留去できるので、該ハ
ロゲン化炭化水素類と分離でき、しかも、１４１bは該
混合物から容易に回収できて再使用が可能であることを
見出したことに基づいて本発明を完成させた。すなわ
ち、本発明は、比較的高沸点のハロゲン化炭化水素とフ
ッ化水素の混合物に１４１bを加えて蒸留し、フッ化水
素を１４１bとの混合物として抜き出すことによる該ハ
ロゲン化炭化水素とフッ化水素の分離方法を要旨とす
る。また本発明は、上のようにして抜き出した混合物を
相分離させ１４１bに富む層と、フッ化水素に富む層に
分離させることをも要旨とする。Means for Solving the Problems The present inventor has conducted earnest studies for solving the above problems. As a result, a mixture of relatively high-boiling halogenated hydrocarbons and hydrogen fluoride is
When 41b is added and distilled, hydrogen fluoride is azeotroped with 141b and can be distilled off as a mixture thereof, so that it can be separated from the halogenated hydrocarbons, and 141b can be easily recovered from the mixture. The present invention was completed based on the finding that it can be reused. That is, the present invention is to add 141b to a mixture of a halogenated hydrocarbon and hydrogen fluoride having a relatively high boiling point and distill the mixture to extract hydrogen fluoride as a mixture with 141b. The gist is the separation method of. Further, the gist of the present invention is that the mixture extracted as described above is phase-separated into a layer rich in 141b and a layer rich in hydrogen fluoride.
【０００６】本明細書において、比較的高沸点のハロゲ
ン化炭化水素とは、ＣＦ3ＣＨ2ＣＦ2ＣＨ3(以下ＨＦＣ
３６５mfcと略す)、ＣＦ3ＣＨ2ＣＨ2Ｃl(以下２５３と
略す)、ＣＨ2＝ＣＣl2(以下１１３０と略す)、ＣＨＣl2
ＣＨ3(以下１５０aと略す)、ＣＨＣl3(以下２０と略
す)、ＣＦ2ＨＣＨ2ＣＨ2Ｃl(以下２６２と略す)、ＣＦ2
ＣlＣＨ2ＣＦ2ＣＨ3(以下３６４lfcと略す)、ＣＨ3ＣＣ
l3(以下１４０aと略す)、ＣＨＣl＝ＣＣl2(以下１１２
０と略す)、ＣＨ2ＣlＣＨ2Ｃl(以下１５０と略す)、Ｃ
ＦＣl2ＣＨ2ＣＦ2ＣＨ3（以下３６３kfcと略す）、ＣＦ
Ｃl2ＣＨ2ＣＦＣlＣＨ3（以下３６２kfbと略す）、ＣＦ
Ｃl2ＣＨ2ＣＣｌ2ＣＨ3(以下３６１kfaと略す)若しくは
ＣＣl3ＣＨ2ＣＦＣlＣＨ3（以下３６１jfbと略す）、ま
たはそれらの混合物等を言う。これらの化合物が少なく
とも１種以上フッ化水素に含まれる場合に本発明は適用
できる。In the present specification, a halogenated hydrocarbon having a relatively high boiling point means CF 3 CH 2 CF 2 CH 3 (hereinafter referred to as HFC).
365 mfc), CF 3 CH 2 CH 2 Cl (hereinafter abbreviated as 253), CH 2 = CCl 2 (hereinafter abbreviated as 1130), CHCl 2
CH 3 (hereinafter abbreviated as 150a), CHCl 3 (hereinafter abbreviated as 20), CF 2 HCH 2 CH 2 Cl (hereinafter abbreviated as 262), CF 2
ClCH 2 CF 2 CH 3 (hereinafter abbreviated as 364lfc), CH 3 CC
l 3 (hereinafter abbreviated as 140a), CCl = CCl 2 (hereinafter 112)
0), CH 2 ClCH 2 Cl (abbreviated as 150 below), C
FCl 2 CH 2 CF 2 CH 3 (hereinafter abbreviated as 363 kfc), CF
Cl 2 CH 2 CFClCH 3 (hereinafter abbreviated as 362 kfb), CF
Cl 2 CH 2 CCl 2 CH 3 (hereinafter abbreviated as 361 kfa) or CCl 3 CH 2 CFClCH 3 (hereinafter abbreviated as 361 jfb), or a mixture thereof. The present invention is applicable when at least one of these compounds is contained in hydrogen fluoride.
【０００７】本発明の方法においては、高沸点ハロゲン
化炭化水素とフッ化水素との混合物に１４１bを加えて
蒸留する。加えるべき１４１bの量は、フッ化水素１モ
ルに対し０.４〜２０モル、好ましくは０.５〜５モルで
ある。１４１bの量が０.４モルより少ない場合、混合物
からのフッ化水素と１４１bの混合物の分離性が悪くな
るため、蒸留分離するためには高段数の塔を必要とし好
ましくない。又１４１bの量が２０モルを越える場合
は、分離性は良くなるものの、処理できる高沸点ハロゲ
ン化炭化水素とフッ化水素との混合物の量が少なくなる
ため、限られた蒸留塔に対して効率的でない。蒸留温度
は、蒸留塔の塔底温度３０〜１２０℃、好ましくは４０
〜６０℃の範囲とし、蒸留圧力１〜１２kg／cm2、好ま
しくは２〜７kg／cm2の範囲とする。一定圧力の下でフ
ッ化水素、高沸点ハロゲン化炭化水素および１４１bの
混合液を加熱していくと、留出物の温度は次第に上昇
し、一定の沸点を示し、１４１bとフッ化水素との混合
物が留去されてくる。この混合物は、例えば圧力３kg／
cm2では温度３８℃を示し、その組成は１４１b ３４モ
ル、フッ化水素 ６６モルであって、高沸点ハロゲン化
炭化水素を含有しない。該混合物は、系外に抜き出して
凝縮させる。なお、蒸留器中の１４１bは混合物として
抜き出されるので、フッ化水素に対する１４１bの割合
が前記範囲を維持するように１４１bを追加する。この
ようにして蒸留を続けると、フッ化水素は１４１bとの
混合物として蒸留器外へ抜き出され、蒸留器には高沸点
ハロゲン化炭化水素及び１４１bが残留し、かくしてフ
ッ化水素と高沸点ハロゲン化炭化水素は分離される。In the method of the present invention, 141b is added to a mixture of a high boiling halogenated hydrocarbon and hydrogen fluoride and distilled. The amount of 141b to be added is 0.4 to 20 mol, preferably 0.5 to 5 mol, based on 1 mol of hydrogen fluoride. When the amount of 141b is less than 0.4 mol, the separability of the mixture of hydrogen fluoride and 141b from the mixture deteriorates, and thus a column with a high number of stages is required for separation by distillation, which is not preferable. On the other hand, when the amount of 141b exceeds 20 moles, the separability is improved, but the amount of the mixture of the high-boiling-point halogenated hydrocarbon and hydrogen fluoride that can be treated is small, so that the efficiency is limited to a limited distillation column. Not relevant. The distillation temperature is 30 to 120 ° C, preferably 40 at the bottom temperature of the distillation column.
The distillation pressure is in the range of 1 to 12 kg / cm 2 , preferably 2 to 7 kg / cm 2 . When a mixed solution of hydrogen fluoride, a high-boiling halogenated hydrocarbon and 141b is heated under a constant pressure, the temperature of the distillate gradually rises and shows a constant boiling point. The mixture is distilled off. This mixture has, for example, a pressure of 3 kg /
In cm 2 , the temperature is 38 ° C., and the composition is 34 mol of 141b and 66 mol of hydrogen fluoride, which does not contain a high boiling halogenated hydrocarbon. The mixture is taken out of the system and condensed. Since 141b in the still is extracted as a mixture, 141b is added so that the ratio of 141b to hydrogen fluoride maintains the above range. When the distillation is continued in this way, hydrogen fluoride is extracted out of the still as a mixture with 141b, and the high boiling halogenated hydrocarbon and 141b remain in the still so that hydrogen fluoride and the high boiling halogen are removed. The hydrocarbons are separated.
【０００８】抜き出された混合物は４０℃以下の温度に
すると、１４１bに富む層とフッ化水素とに液／液分離
する。例えば２０℃の場合、１４１bに富む層は、約９
９重量％の１４１bと約１重量％のフッ化水素よりな
り、フッ化水素を富む層は約１８重量％の１４１bと約
８２重量％のフッ化水素よりなる。１４１bに富む層は
ほとんどフッ化水素を含まないので、本発明の高沸点ハ
ロゲン化炭化水素とフッ化水素との混合物の蒸留に際し
て加えるべき１４１bとして使用できる。かくして１４
１bはリサイクルして使用できる。フッ化水素に富む層
はさらに蒸留してフッ化水素と１４１bに分離すること
もできるが、１４０aとフッ化水素との反応系あるいは
１４１bの分離工程に加えるのが得策である。When the extracted mixture is heated to a temperature of 40 ° C. or lower, it undergoes liquid / liquid separation into a layer rich in 141b and hydrogen fluoride. For example, at 20 ° C, a layer rich in 141b has about 9
9 wt% 141b and about 1 wt% hydrogen fluoride, and the hydrogen fluoride-rich layer is about 18 wt% 141b and about 82 wt% hydrogen fluoride. Since the 141b-rich layer contains almost no hydrogen fluoride, it can be used as 141b to be added in the distillation of the mixture of the high-boiling halogenated hydrocarbon of the present invention and hydrogen fluoride. Thus 14
1b can be recycled and used. The layer rich in hydrogen fluoride can be further distilled to separate it into hydrogen fluoride and 141b, but it is advisable to add it to the reaction system of 140a and hydrogen fluoride or to the step of separating 141b.
【０００９】[0009]
【実施例】スチル部の容量が３lで理論段数２０段の塔
を有し、冷却温度０℃の凝縮器を備えた蒸留塔に約１７
モルの１４１bを加えた。スチル部の温度４０℃で１４
１bの全還流状態にした。そこへ、３６５mfc、３６４lf
c、３６３kfc、３６２kfb、３６１kfaを合計で２モル％
含むフッ化水素を７.９モル／時間の割合で蒸留塔底部
より加えた。約１０分後凝縮器で還流される液は、１４
１bとフッ化水素との混合物で１４１bとフッ化水素のモ
ル比は３４対６６であった。この混合物を、１１.９モ
ル／時間の割合で抜き出した。蒸留塔の塔頂からは、１
４１bが４.１モル／時間、フッ化水素が７.７モル／時
間の割合で抜き出されたことになる。この操作により塔
頂から抜き出されたフッ化水素と１４１bの混合物中に
含まれる副生成物類は、抜き出された１４１bに対して
０.０１モル％以下であった。さらに蒸留塔中段に１４
１bを４.２モル／時間の割合で加え、スチル部より高沸
点ハロゲン化炭化水素を含む１４１bを０.１１モル／時
間の割合で抜き出した。本操作を続けるにしたがい、穏
やかな塩化水素及び１４２b等の発生があり、系内圧力
が穏やかに増加するため、一定の圧力を保持するよう
に、塩化水素及び１４２b等は凝縮器上部より非凝縮ガ
スとして放出した。蒸留塔へ供給した１４１bとフッ化
水素は各々合計で １４１b ４.２モル／時間 フッ化水素 ７.９モル／時間 となり、１４１b対フッ化水素のモル比は、フッ化水素
の１に対して１４１bが０.５３倍であった。本操作を５
時間継続後、スチル部より抜き出される１４１bは約４.
５モル％の副生成物類を含有していた。さらに塔頂より
抜き出された１４１bとフッ化水素の混合物を２０℃以
下に保って、１４１bに富む相とフッ化水素に富む相と
の２相に分離した。ここで１４１bに富む相とは、概ね
１重量％のフッ化水素を含む１４１bの相であり、フッ
化水素に富む相とは、概ね１８重量％の１４１bを含む
フッ化水素の相であった。１４１bに富む相は、前述の
蒸留塔中段に加えた１４１bとして使用可能であるし、
フッ化水素に富む相は、通常反応器へリサイクルされ
る。又わずかに抜き出された高沸点ハロゲン化炭化水素
を含む１４１bは、通常焼却される。EXAMPLE A distillation column having a still section with a capacity of 3 liters and a theoretical plate number of 20 and a condenser having a cooling temperature of 0.degree.
Molar 141b was added. 14 at still temperature of 40 ℃
It was brought to a total reflux state of 1b. 365mfc, 364lf there
c, 363 kfc, 362 kfb, 361 kfa in total of 2 mol%
The contained hydrogen fluoride was added from the bottom of the distillation column at a rate of 7.9 mol / hour. After about 10 minutes, the liquid returned to the condenser is 14
In the mixture of 1b and hydrogen fluoride, the molar ratio of 141b and hydrogen fluoride was 34:66. This mixture was withdrawn at a rate of 11.9 mol / hour. 1 from the top of the distillation column
41b was extracted at a rate of 4.1 mol / hour, and hydrogen fluoride was extracted at a rate of 7.7 mol / hour. By-products contained in the mixture of hydrogen fluoride and 141b extracted from the column top by this operation were 0.01 mol% or less based on the extracted 141b. Furthermore, 14 in the middle stage of the distillation column
1b was added at a rate of 4.2 mol / hour, and 141b containing a high-boiling halogenated hydrocarbon was extracted from the still portion at a rate of 0.11 mol / hour. As this operation continues, mild hydrogen chloride, 142b, etc. are generated, and the system pressure gently increases. Emitted as gas. The total amount of 141b and hydrogen fluoride supplied to the distillation column was 141b 4.2 mol / hr hydrogen fluoride 7.9 mol / hr, and the molar ratio of 141b to hydrogen fluoride was 1 mol of hydrogen fluoride. 141b was 0.53 times. This operation is 5
After the time continues, 141b pulled out from the still part is about 4.
It contained 5 mol% by-products. Further, the mixture of 141b and hydrogen fluoride extracted from the top of the column was kept at 20 ° C. or lower and separated into two phases, a phase rich in 141b and a phase rich in hydrogen fluoride. Here, the 141b-rich phase was the phase of 141b containing approximately 1% by weight of hydrogen fluoride, and the hydrogen fluoride-rich phase was the phase of hydrogen fluoride containing approximately 18% by weight of 141b. . The phase rich in 141b can be used as 141b added to the middle stage of the above-mentioned distillation column,
The hydrogen fluoride-rich phase is usually recycled to the reactor. Further, 141b containing a small amount of the high-boiling-point halogenated hydrocarbons extracted is usually incinerated.
【００１０】[0010]
【発明の効果】フッ化水素と高沸点ハロゲン化炭化水素
が効率的に分離でき、分離したフッ化水素は再使用可能
となる。The hydrogen fluoride and the high-boiling halogenated hydrocarbon can be efficiently separated, and the separated hydrogen fluoride can be reused.
フロントページの続き (72)発明者 本多 宏之 大阪府摂津市西一津屋１番１号 ダイキン 工業株式会社淀川製作所内 (72)発明者 小松 聡 大阪府摂津市西一津屋１番１号 ダイキン 工業株式会社淀川製作所内Front page continuation (72) Hiroyuki Honda, 1-1 Nishiichitsuya, Settsu City, Osaka Prefecture Daikin Industries, Ltd. Yodogawa Manufacturing Co., Ltd. (72) Satoshi Komatsu 1-1, Nishiichitsuya, Settsu City, Osaka Prefecture Daikin Industries, Ltd. Yodogawa Factory
Claims (5)
素と反応させて１,１−ジクロロ−１−フルオロエタン
と１−クロロ−１,１−ジフルオロエタンを生成させる
反応において副生する高沸点ハロゲン化炭化水素とフッ
化水素との混合物に、１,１−ジクロロ−１−フルオロ
エタンを加えて蒸留し、フッ化水素を１,１−ジクロロ
フルオロエタンとの混合物とし留去することよりなる、
該ハロゲン化炭化水素とフッ化水素の分離方法。1. A high boiling point which is a by-product in the reaction of reacting 1,1,1-trichloroethane with hydrogen fluoride to produce 1,1-dichloro-1-fluoroethane and 1-chloro-1,1-difluoroethane. 1,1-dichloro-1-fluoroethane is added to a mixture of a halogenated hydrocarbon and hydrogen fluoride for distillation, and hydrogen fluoride is removed as a mixture with 1,1-dichlorofluoroethane. ,
A method for separating the halogenated hydrocarbon and hydrogen fluoride.
Ｈ2ＣＦ2ＣＨ3、ＣＦ3ＣＨ2ＣＨ2Ｃl、ＣＨ2＝ＣＣl2、
ＣＨＣl2ＣＨ3、ＣＨＣl3、ＣＦ2ＨＣＨ2ＣＨ2Ｃl、Ｃ
Ｆ2ＣlＣＨ2ＣＦ2ＣＨ3、ＣＨ3ＣＣl3、ＣＨＣl＝ＣＣl
2、ＣＨ2ＣlＣＨ2Ｃl、ＣＦＣl2ＣＨ2ＣＦ2ＣＨ3、ＣＦ
Ｃl2ＣＨ2ＣＦＣlＣＨ3、ＣＦＣl2ＣＨ2ＣＣｌ2ＣＨ3若
しくはＣＣl3ＣＨ2ＣＦＣlＣＨ3、またはそれらの混合
物である請求項１に記載の方法。2. The high-boiling halogenated hydrocarbon is CF 3 C.
H 2 CF 2 CH 3 , CF 3 CH 2 CH 2 Cl, CH 2 = CCl 2 ,
CHCl 2 CH 3 , CHCl 3 , CF 2 HCH 2 CH 2 Cl, C
F 2 ClCH 2 CF 2 CH 3 , CH 3 CCl 3 , CHCl = CCl
2 , CH 2 ClCH 2 Cl, CFCl 2 CH 2 CF 2 CH 3 , CF
The method according to claim 1, which is Cl 2 CH 2 CFClCH 3 , CFCl 2 CH 2 CCl 2 CH 3 or CCl 3 CH 2 CFClCH 3 , or a mixture thereof.
オロエタンの量がフッ化水素１モルに対して、０.４〜
２０モルである請求項１に記載の方法。3. The amount of 1,1-dichloro-1-fluoroethane to be added is 0.4 to 1 mol based on 1 mol of hydrogen fluoride.
The method according to claim 1, which is 20 mol.
３０℃〜１２０℃で圧力１〜１２kg／cm2である請求項
１に記載の方法。4. The method according to claim 1, wherein the distillation conditions are a temperature of the still portion of the distillation column of 30 ° C. to 120 ° C. and a pressure of 1 to 12 kg / cm 2 .
ジクロロ−１−フルオロエタンに富む層とフッ化水素に
富む層に分離する請求項１に記載の方法。5. The distilled mixture is phase-separated to give 1,1-
The method according to claim 1, wherein a layer rich in dichloro-1-fluoroethane and a layer rich in hydrogen fluoride are separated.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4311812A JP2661489B2 (en) | 1992-11-20 | 1992-11-20 | Method for separating high boiling halogenated hydrocarbons and hydrogen fluoride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4311812A JP2661489B2 (en) | 1992-11-20 | 1992-11-20 | Method for separating high boiling halogenated hydrocarbons and hydrogen fluoride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06157366A true JPH06157366A (en) | 1994-06-03 |
| JP2661489B2 JP2661489B2 (en) | 1997-10-08 |
Family
ID=18021716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4311812A Expired - Fee Related JP2661489B2 (en) | 1992-11-20 | 1992-11-20 | Method for separating high boiling halogenated hydrocarbons and hydrogen fluoride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2661489B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6518467B2 (en) | 2000-12-29 | 2003-02-11 | Honeywell International Inc. | Method of making hydrofluorocarbons and hydrochlorofluorocarbons |
| CN108299225A (en) * | 2018-01-13 | 2018-07-20 | 安徽金禾实业股份有限公司 | A kind of method and device recycling trichloroethanes and DMF |
| WO2020196843A1 (en) * | 2019-03-28 | 2020-10-01 | ダイキン工業株式会社 | Azeotropic or azeotropic-like composition comprising hydrogen fluoride and 1,1,2-trichloroethane, trans-1,2-dichloroethylene or cis-1,2-dichloroethylene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58217403A (en) * | 1982-06-08 | 1983-12-17 | ペンウオルト・コ−ポレ−シヨン | Anhydrous phase separation for recovering hydrogen fluoride from fluorination |
| JPH02196734A (en) * | 1989-01-26 | 1990-08-03 | Daikin Ind Ltd | Separation of 1,1-dichloro-1-fluoroethane from mixture of hydrogen fluoride and 1,1-dichloro-1-fluoroethane |
| JPH02295937A (en) * | 1989-05-04 | 1990-12-06 | Pennwalt Corp | Method for separating 1,1-dichloro-1-fluoroethane from 1,1,1,3,3-pentafluorobutane |
-
1992
- 1992-11-20 JP JP4311812A patent/JP2661489B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58217403A (en) * | 1982-06-08 | 1983-12-17 | ペンウオルト・コ−ポレ−シヨン | Anhydrous phase separation for recovering hydrogen fluoride from fluorination |
| JPH02196734A (en) * | 1989-01-26 | 1990-08-03 | Daikin Ind Ltd | Separation of 1,1-dichloro-1-fluoroethane from mixture of hydrogen fluoride and 1,1-dichloro-1-fluoroethane |
| JPH02295937A (en) * | 1989-05-04 | 1990-12-06 | Pennwalt Corp | Method for separating 1,1-dichloro-1-fluoroethane from 1,1,1,3,3-pentafluorobutane |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6518467B2 (en) | 2000-12-29 | 2003-02-11 | Honeywell International Inc. | Method of making hydrofluorocarbons and hydrochlorofluorocarbons |
| CN108299225A (en) * | 2018-01-13 | 2018-07-20 | 安徽金禾实业股份有限公司 | A kind of method and device recycling trichloroethanes and DMF |
| WO2020196843A1 (en) * | 2019-03-28 | 2020-10-01 | ダイキン工業株式会社 | Azeotropic or azeotropic-like composition comprising hydrogen fluoride and 1,1,2-trichloroethane, trans-1,2-dichloroethylene or cis-1,2-dichloroethylene |
| JP2020164435A (en) * | 2019-03-28 | 2020-10-08 | ダイキン工業株式会社 | Azeotropic or azeotrope-like composition including 1,1,2-trichloroethane, trans-1,2-dichloroethylene, or cis-1,2-dichloroethylene, and hydrogen fluoride |
| CN113677651A (en) * | 2019-03-28 | 2021-11-19 | 大金工业株式会社 | Azeotropic or azeotrope-like compositions comprising 1,1, 2-trichloroethane, trans-1, 2-dichloroethylene or cis-1, 2-dichloroethylene and hydrogen fluoride |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2661489B2 (en) | 1997-10-08 |
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