JPH02188537A - Production of 2,2-dichloro-1,1,1,2-tetrafluoroethane - Google Patents
Production of 2,2-dichloro-1,1,1,2-tetrafluoroethaneInfo
- Publication number
- JPH02188537A JPH02188537A JP1007056A JP705689A JPH02188537A JP H02188537 A JPH02188537 A JP H02188537A JP 1007056 A JP1007056 A JP 1007056A JP 705689 A JP705689 A JP 705689A JP H02188537 A JPH02188537 A JP H02188537A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- tetrafluoroethane
- catalyst
- trifluoroethane
- trichloro
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 title abstract 2
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 9
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 238000006317 isomerization reaction Methods 0.000 claims description 6
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000003507 refrigerant Substances 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 238000003682 fluorination reaction Methods 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 4
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、適度な安定性を有する冷媒である１、１．１
．２−テトラフルオロエタンの原料として有用な２，２
−ジクロロ−１，１，１，２−テトラフルオロエタン（
以後、Ｒ−１１４ａと略す、）の製造法に関、する。[Detailed Description of the Invention] [Industrial Application Field] The present invention is directed to refrigerants 1, 1.1, which are moderately stable refrigerants.
．． 2,2 useful as a raw material for 2-tetrafluoroethane
-dichloro-1,1,1,2-tetrafluoroethane (
Hereinafter, it will be abbreviated as R-114a).
［従来技術とその解決しようとする課題］従来、Ｒ−１
１４ａを製造するには１，１．２−トリクロロ−１，２
，２−トリフルオロエタン（以後、Ｒ−１１３と略す、
）を触媒の存在下、フッ化水素でフッ素化する方法が知
られている。[Prior art and problems to be solved] Conventionally, R-1
To produce 14a, 1,1,2-trichloro-1,2
, 2-trifluoroethane (hereinafter abbreviated as R-113,
) with hydrogen fluoride in the presence of a catalyst is known.
この反応に使われる触媒としては、■塩化アルミニウム
をフッ素化したフッ化アルミニウム（米国特許第２．７
４８．１７７号）■工業的製造法による市販のフッ化ア
ルミニウム粉末［にＪｅｃｃｈｉｏ。Catalysts used in this reaction include: ■ Aluminum fluoride, which is fluorinated aluminum chloride (U.S. Patent No. 2.7)
48.177) ■ Commercially available aluminum fluoride powder by industrial production method [Jecchio.
Ｇ、Ｇｒｏｐｐｅｌｌｉ、Ｊ、Ｃ，Ｔａｔｌｏｗ、Ｊ、
Ｆｌｕｏｒｉｒｉｅ Ｃｈｅｓ＋、４゜１１７ （１９
７４） ］■酸化クロム［Ｌ、Ｍａｒａｎｇｏｎｉ ｅ
ｔ ａｔ、。G., Groppelli, J., C. Tatlow, J.
Fluoririe Ches+, 4°117 (19
74) ]■Chromium oxide [L, Marangoni e
t at,.
Ｃｈｉｍ、Ｉｎｄ、（Ｍｉｌａｎ）、、６４，１３５
（１９８２）］ 等が提案されている。このような反
応においては、触媒の調整方法や反応条件を最適化する
ことによってＲ−１１４ａの収率を相当程度まで向上さ
せることが可能である。しかしながらこの場合、Ｒ−１
１４ａの異性体である１、２−ジクロロ−１，１，２，
２−テトラフルオロエタン（以後、Ｒ−１１４と略す、
）の副生は避けられず、またＲ−１１４ａの収率の向上
には限界があり、しかも副生物のＲ−１１４とＲ−１１
４ａは沸点差が０．６℃と非常に小さく、蒸溜分離する
のは極めて困難であるので、純度の高いＲ−１１４ａは
得られない。Chim, Ind. (Milan), 64,135
(1982)] etc. have been proposed. In such a reaction, the yield of R-114a can be improved to a considerable extent by optimizing the catalyst preparation method and reaction conditions. However, in this case, R-1
1,2-dichloro-1,1,2, which is an isomer of 14a
2-tetrafluoroethane (hereinafter abbreviated as R-114,
) is unavoidable, and there is a limit to improving the yield of R-114a.
4a has a very small boiling point difference of 0.6° C. and is extremely difficult to separate by distillation, making it impossible to obtain highly pure R-114a.
［課題を解決するための手段］
本発明者らはこのような現状に鑑み、経済的かつ工業的
に有利なＲ−１１４ａの製造方法につき種々の検討を行
い、Ｒ−１１３からＲ（１４ａを高収率で製造するには
、Ｒ−１１４の副生を抑制することが必須であるとの結
論より、本発明のプロセスに到達したものである。[Means for Solving the Problems] In view of the current situation, the present inventors conducted various studies on an economically and industrially advantageous method for producing R-114a, and obtained R-113 to R(14a). The process of the present invention was arrived at from the conclusion that it is essential to suppress the by-product of R-114 in order to produce it in high yield.
すなわち本発明は゛、Ｒ−１１３からＲ−１１３ａへの
異性化反応を行った後、触媒の存在下にフッ化水素との
反応を行うことを特徴とするＲ（１４ａの製造方法であ
る。That is, the present invention is a method for producing R(14a), which is characterized by carrying out an isomerization reaction from R-113 to R-113a, and then carrying out a reaction with hydrogen fluoride in the presence of a catalyst.
この場合、ト１１３からＲ−１１３ａの異性化反応を行
った後、生成物を特に精製することなく、次のフッ素化
工程を行うこともできる。In this case, after performing the isomerization reaction of R-113a from T-113, the next fluorination step can be performed without particularly purifying the product.
本発明において、Ｒ−１１３からＲ−１１３ａへの異性
化反応を第１工程、次のフッ素化の工程を第２工程とす
ると、第１工程としては■Ｒ−１１３に触媒を添加し、
加熱することより成る液相反応、■Ｒ−１１３を２５０
℃以上に加熱したフッ化アルミニウムに接触させること
より成る気相反応の二つの方法があり、いずれの方法も
本発明に含まれる。In the present invention, if the isomerization reaction from R-113 to R-113a is the first step, and the subsequent fluorination step is the second step, the first step is: (1) adding a catalyst to R-113;
Liquid phase reaction consisting of heating ■ R-113 at 250°C
There are two methods of gas phase reaction consisting of contacting aluminum fluoride heated to temperatures above .degree. C., both of which are included in the present invention.
また第２工程としては、第１の工程で得られたＲ−１１
３ａとフッ化水素の混合物を各種の方法で作成したフッ
化アルミニウム、フッ化クロムまたはその他の触媒と接
触させることからなる気相フッ素化反応が利用できる。In addition, as the second step, R-11 obtained in the first step
A gas phase fluorination reaction consisting of contacting a mixture of 3a and hydrogen fluoride with variously prepared aluminum fluoride, chromium fluoride or other catalysts is available.
第１の工程で得られるＲ−１１３ａの純度を高くするの
は好ましいが、必ずしもＲ−１１３を殆ど含まないＲ−
１１３ａにする必要は無い、 Ｒ−１１３ａとＲ−１１
３の混合物を第２の工程でフッ素化する場合、Ｒ１１３
ａはＲ−１１４ａとなり、Ｒ−１１３の一部はＲ−１１
４となり大部分はＲ−１１４ａになると考えられる。従
ってＲ−１１３とＲ−１１３ａの混合物を原料とした場
合もＲ−１１３とＲ−１１３ａの比率に応じてＲ−１１
４ａの収率が向上し、本発明に含まれる。Although it is preferable to increase the purity of R-113a obtained in the first step, it is not necessary to increase the purity of R-113a obtained in the first step.
There is no need to make it 113a, R-113a and R-11
When the mixture of R113 is fluorinated in the second step, R113
a becomes R-114a, and a part of R-113 becomes R-11
4, and most of it is thought to be R-114a. Therefore, even when a mixture of R-113 and R-113a is used as a raw material, R-11
The yield of 4a is improved and is included in the present invention.
本発明によって得られるＲ−１１４ａは公知の反応すな
わちＲ−１１４ａと水素との反応により、適当な安定性
を有し、冷媒として有用な１，１．１．２−テトラフル
オロエタン（以後、Ｒ−１３４ａと略す、）に変換する
ことができる。上記方法で使用される触媒としては、種
々の担体にパラジウムを担持させた触媒等があり、本出
願人の提案した発明の名称ｒ １．１．１．２−テトラ
フルオロエタンの製造法」特願昭６３−１３２３９５の
方法、すなわちＲ−１１４ａ等を活性アルミナ担持パラ
ジウム触媒の存在下、１２０〜２００℃未満の温度範囲
で水素と反応させることにより、目的のＲ−１３４＆を
製造することができる。R-114a obtained by the present invention has appropriate stability by a known reaction, that is, the reaction of R-114a with hydrogen, and is useful as a refrigerant. -134a). Catalysts used in the above method include catalysts in which palladium is supported on various carriers. The desired R-134& can be produced by the method of Application No. 63-132395, that is, by reacting R-114a etc. with hydrogen in the presence of an activated alumina-supported palladium catalyst at a temperature range of 120 to less than 200°C. .
［実施例］
以下、実施例により本発明を具体的に説明するが、本発
明は係る実施例に限定されるものではない。[Examples] Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.
実施例１
還流冷却器と撹拌機を設けた容量１１のガラス製画ツロ
フラスコにＲ−１１３を５００ｇと、触媒として粉末に
した無水塩化アルミニウム２０ｇを入れ、撹拌しながら
フラスコを加熱し、内部の液体が沸騰した状態を３時間
保った。Example 1 500 g of R-113 and 20 g of anhydrous aluminum chloride powdered as a catalyst were placed in a glass flask with a capacity of 11 equipped with a reflux condenser and a stirrer, and the flask was heated with stirring to remove the liquid inside. was kept boiling for 3 hours.
反応生成物を水で洗浄、塩化カルシウム乾燥してガスク
ロマトグラフィーと”ｌＦｎｍｒで分析したところ、Ｒ
−１１４ａ ： ２．５ｅｅｔＬ Ｒ−１１３ａ ：
９４．２ｗｔχであり、ト１１３の転化率は１００ｗｔ
χ、Ｒ−１１３ａの収率は９４．２χとなった。The reaction product was washed with water, dried with calcium chloride, and analyzed by gas chromatography and IFnmr.
-114a: 2.5eetL R-113a:
94.2wtχ, and the conversion rate of To113 is 100wt
The yield of R-113a was 94.2χ.
この反応生成物を蒸溜して９９．９ｗｔ％以上の純度の
Ｒ−１１３＆を得た。This reaction product was distilled to obtain R-113& with a purity of 99.9 wt% or more.
次に、上述の異性化工程得られたものの蒸溜生成物（Ｒ
−１１３ａ ： ９９．９ｗｔ％以上）を原料として以
下に示す反応を行った。Next, the distillation product (R
-113a: 99.9 wt% or more) was used as a raw material to carry out the reaction shown below.
すなわち、直径５膳鳳のγ−アルミナ２００ ｃｃを直
径５Ｃ■、長さ５０ｃｍの円筒形ＳＵＳ反応管に充填し
た。窒素ガスを流しながら３００℃まで昇温し、１時間
保った後、その温度で窒素に同伴したフッ化水素ガスを
供給した。充填された触媒のフッ素化によるホットスポ
ットが出口に達したところで、反応器温度を４００℃に
上げ、その状態を１時間保ち触媒調整を行った。That is, 200 cc of γ-alumina with a diameter of 5 cm was filled into a cylindrical SUS reaction tube with a diameter of 5 C and a length of 50 cm. The temperature was raised to 300° C. while flowing nitrogen gas, and after keeping it for 1 hour, hydrogen fluoride gas accompanied by nitrogen was supplied at that temperature. When the hot spot due to fluorination of the packed catalyst reached the outlet, the reactor temperature was raised to 400°C, and this state was maintained for 1 hour to adjust the catalyst.
このように調整した触媒２００ ｃｃを充填しである前
記反応管の温度を３００℃に保ち、そこへ上記蒸溜生成
物とフッ化水素をそれぞれ０．５ｍｏｌ／ｈｒ、０．５
■ｏｌ／ｈｒで導入した０反応品出ロガスをガスクロマ
トグラフィーにより分析したところ、Ｒ−１１４ａ ：
５５．５ｗｔＺとなり、Ｒ−１１３ａの転化率は５５
，６ＩＩＩＬχ、Ｒ−１１４ａの収率は９９．８χとな
った。これにより初めの原料であるＲ−１１３からＲ−
１１４ａまでの通算の収率を計算すると９６．５Ｘどな
った。The temperature of the reaction tube filled with 200 cc of the catalyst prepared in this way was kept at 300°C, and the distillation product and hydrogen fluoride were added thereto at 0.5 mol/hr and 0.5 ml/hour, respectively.
■When the 0-reaction product log gas introduced at ol/hr was analyzed by gas chromatography, it was found that R-114a:
55.5wtZ, and the conversion rate of R-113a is 55.
, 6IIILχ, the yield of R-114a was 99.8χ. This allows the initial raw material R-113 to become R-
The total yield up to 114a was calculated to be 96.5X.
また本実施例の生成物を蒸溜したところ、問題となるＲ
−１１４は０．１社％以下の含量であった。Furthermore, when the product of this example was distilled, the problematic R
-114 had a content of 0.1% or less.
実施例２
上部に還流冷却器と撹拌機を設けた直径５Ｃ■、高さ３
０ｃｍのガラス製反応管に４００ ｃｃのＲ−１１３と
触媒として粉末の無水塩化アルミニウム１５ｇを入れ、
撹拌しながら反応管を加熱し内部の液体が沸騰した状態
で外部への溜出のない状態を２時間保った。その後、上
部からＲ−１１３を５ｇ／ｗｉｎで滴下し、液高の変化
のないように還流冷却器から生成物を流出させた。この
状態で２時間後から５時間にわたって生成物を捕集した
ところ生成物は１５００ｇであり、その組成をガスクロ
マトグラフと１９Ｆｎ■ｒで分析したところ、Ｒ−１１
４ａ ：１．２ｗｔχ、Ｒ−１１３ａ： ９０．２ｗｔ
！ 、 Ｒ−１１３： ８．６ｗｔχであった。Example 2 Diameter 5C■, height 3 with reflux condenser and stirrer on top
Put 400 cc of R-113 and 15 g of powdered anhydrous aluminum chloride as a catalyst into a 0 cm glass reaction tube.
The reaction tube was heated while stirring, and the liquid inside was kept boiling for 2 hours without spilling to the outside. Thereafter, R-113 was added dropwise from the top at a rate of 5 g/win, and the product was allowed to flow out from the reflux condenser without changing the liquid level. When the product was collected in this state for 5 hours from 2 hours later, the product amount was 1500g, and its composition was analyzed using a gas chromatograph and 19Fnr, and it was found that R-11
4a: 1.2wtχ, R-113a: 90.2wt
! , R-113: 8.6wtχ.
ここで得られた生成物を精製することなく、実施例１で
使用したフッ素化反応器および触媒を用い、実施例１と
同様の方法でフッ素化を行った。この際の反応温度は３
３０℃であり、異性化生成物とフッ素の導入蓋はそれぞ
れ０．５ｓ＋ｏｌ／ｈｒ、０．５ｓｏｌ／ｈｒである０
反応品出ロガスを分析したところ、Ｒ−１１４ａ ：
５８．Ｏｗｔ！となり、フッ素化反応の原料となるＲ−
１１３ａおよびＲ−１１３の転化率は６０．５ｗｔｚ、
Ｒ−１１３ｈ’らＲ−１１４ａＡ、、ノ収率＋、ｔ９７
．Ｏｚとなった。Fluorination was performed in the same manner as in Example 1 using the fluorination reactor and catalyst used in Example 1 without purifying the product obtained here. The reaction temperature at this time was 3
The temperature is 30°C, and the isomerization product and fluorine introduction lids are 0.5 s+ol/hr and 0.5 sol/hr, respectively.
Analysis of the reaction product log gas revealed that R-114a:
58. Owt! and R-, which is the raw material for the fluorination reaction.
The conversion rate of 113a and R-113 is 60.5wtz,
R-113h' et R-114aA, yield +, t97
．． It became Oz.
このフッ素化生成物を蒸溜精製したＲ−１１４ａには、
Ｒ−１１４が０．５ｗｔχ含まれていた。R-114a, which is purified by distillation of this fluorinated product, has
It contained 0.5wtχ of R-114.
比較例
実施例１のフッ素化反応で用いたで反応器および触媒を
使用してＲ−１１３のフッ化水素との反応を、反応温度
を３６０℃にした他は同様にして行った。Comparative Example Using the reactor and catalyst used in the fluorination reaction of Example 1, the reaction of R-113 with hydrogen fluoride was carried out in the same manner as in Example 1, except that the reaction temperature was changed to 360°C.
この結果、Ｒ−１１４ａ ： ５８．Ｏｗｔχの生成物
が得られ、ト１１３の転化率は６６．４ｗｔχ、Ｒ−Ｉ
Ｌ４ａの収率は８７．３χであった。As a result, R-114a: 58. A product of Owtχ was obtained, and the conversion rate of To113 was 66.4wtχ, R-I
The yield of L4a was 87.3χ.
これを蒸溜したＲ−１１４＆には１１ 、３ｗｔ％のＲ
−１１４が含まれていた。Distilled from this, R-114& contains 11, 3wt% R.
-114 was included.
［発明の効果］
本発明の方法によれば、工業的に製造されているＲ−１
１３を異性化反応により、−旦Ｒ−１１３ａに変換した
後、フッ化水素と反応させることにより、分離するのが
非常に困難なＲ−１１４の含量を効果的に低減させるこ
とができ、工業的に極めて優れたＲ−１１４ａの製造法
である。[Effect of the invention] According to the method of the invention, industrially produced R-1
By converting 13 into R-113a through an isomerization reaction and then reacting it with hydrogen fluoride, the content of R-114, which is very difficult to separate, can be effectively reduced, making it possible to reduce the content of R-114, which is very difficult to separate. This is an extremely excellent method for producing R-114a.
２Ｓ−2S-
Claims (1)
ロエタンから１，１，１−トリクロロ−２，２，２−ト
リフルオロエタンへの異性化反応を行った後、触媒の存
在下にフッ化水素との反応を行うことを特徴とする２，
２−ジクロロ−１，１，１，２−テトラフルオロエタン
の製造方法(1) After performing the isomerization reaction from 1,1,2-trichloro-1,2,2-trifluoroethane to 1,1,1-trichloro-2,2,2-trifluoroethane, the presence of a catalyst 2, characterized by carrying out a reaction with hydrogen fluoride below.
Method for producing 2-dichloro-1,1,1,2-tetrafluoroethane
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1007056A JPH02188537A (en) | 1989-01-13 | 1989-01-13 | Production of 2,2-dichloro-1,1,1,2-tetrafluoroethane |
| US07/357,291 US4996379A (en) | 1988-05-30 | 1989-05-26 | Method of preparing 1,1,1,2-tetrafluoroethane from 1,1-dichloro-1,2,2,2-tetrafluoroethane |
| FR8907005A FR2631959A1 (en) | 1988-05-30 | 1989-05-29 | PROCESS FOR THE PREPARATION OF 1,1,1,2-TETRAFLUOROETHANE FROM 1,1-DICHLORO-1,2,2,2-TETRAFLUOROETHANE |
| IT8920692A IT1230795B (en) | 1988-05-30 | 1989-05-30 | PROCEDURE FOR PREPARING 1,1,1,2 TETRAFLUOROETHANE FROM 1,1 DICHLOR 1,2,2,2 TETRAFLUOROETHANE. |
| GB8912325A GB2219796B (en) | 1988-05-30 | 1989-05-30 | Method of preparing 1,1,1,2-tetrafluoroethane from 1,1-dichloro-1,2,2,2-tetrafluoroethane |
| DE3917573A DE3917573A1 (en) | 1988-05-30 | 1989-05-30 | METHOD FOR PRODUCING 1,1,1,2-TETRAFLUORETHANE FROM 1,1-DICHLOR-1,2,2,2-TETRAFLUORETHANE |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1007056A JPH02188537A (en) | 1989-01-13 | 1989-01-13 | Production of 2,2-dichloro-1,1,1,2-tetrafluoroethane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02188537A true JPH02188537A (en) | 1990-07-24 |
Family
ID=11655411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1007056A Pending JPH02188537A (en) | 1988-05-30 | 1989-01-13 | Production of 2,2-dichloro-1,1,1,2-tetrafluoroethane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02188537A (en) |
-
1989
- 1989-01-13 JP JP1007056A patent/JPH02188537A/en active Pending
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