JPH045247A - Production of 1,1,1,2-tetrafluoroethane - Google Patents
Production of 1,1,1,2-tetrafluoroethaneInfo
- Publication number
- JPH045247A JPH045247A JP10825390A JP10825390A JPH045247A JP H045247 A JPH045247 A JP H045247A JP 10825390 A JP10825390 A JP 10825390A JP 10825390 A JP10825390 A JP 10825390A JP H045247 A JPH045247 A JP H045247A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoroethane
- bromine
- reaction
- reacting
- tetrafluoroethane
- 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.)
- Granted
Links
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 8
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 25
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052794 bromium Inorganic materials 0.000 abstract description 16
- 238000000034 method Methods 0.000 abstract description 15
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 abstract description 10
- TZNJHEHAYZJBHR-UHFFFAOYSA-N 2-bromo-1,1,1-trifluoroethane Chemical compound FC(F)(F)CBr TZNJHEHAYZJBHR-UHFFFAOYSA-N 0.000 abstract description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 abstract description 2
- 229910052801 chlorine Inorganic materials 0.000 abstract description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 abstract description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 2
- 239000003507 refrigerant Substances 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000006227 byproduct Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 4
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical compound [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
１１上ム■月上！
本発明は、１，１，１．２−テトラフルオロエタンの製
造法に関する。さらに詳しくは、本発明は１，１．１−
トリフルオロエタンを臭素化し、次いで当該臭素化物と
フッ化水素とを反応させて１．１，１．２−テトラフル
オロエタンを製造する方法に関する。[Detailed description of the invention] 11th month ■Moon! The present invention relates to a method for producing 1,1,1,2-tetrafluoroethane. More specifically, the present invention provides 1,1.1-
The present invention relates to a method for producing 1,1,1,2-tetrafluoroethane by brominating trifluoroethane and then reacting the brominated product with hydrogen fluoride.
１．１，１．２−テトラフルオロエタンは、現在冷媒と
して盛んに使用されているジクロジフルオロメタン（ｒ
ＣＦＣ−１２Ｊと一般に称される。）の有望な代替品と
されている化合物である。1.1,1.2-Tetrafluoroethane is dichlorodifluoromethane (r), which is currently widely used as a refrigerant.
It is commonly referred to as CFC-12J. ) is a compound that is considered a promising alternative.
゛ の と の口題点
従来から提案されている実用可能性のある１１．１．２
−テトラフルオロエタンの製造方法は、−般に下記の二
つの基本的タイプに分類されうる（−イ）１，１−ジク
ロロ−１，２，２，２−テトラフルオロエタンを水素に
より還元する方法、及び
（ロ）１−クロロ−２，２，２−トリフルオロエタンと
フッ化水素とを反応させる方法。11.1.2 Problems with ゛ and 11.1.2 that have been proposed in the past and have potential for practical use
-Methods for producing tetrafluoroethane can be generally classified into the following two basic types: (i) A method of reducing 1,1-dichloro-1,2,2,2-tetrafluoroethane with hydrogen. , and (b) a method of reacting 1-chloro-2,2,2-trifluoroethane with hydrogen fluoride.
上記（イ）のタイプの方法は、パラジウム、レニウム、
白金等の還元触媒の存在下、はぼ１００〜５００℃程度
の範囲内の温度で反応を実施するものであるが、目的生
成物である１、１，１．２−テトラフルオロエタンより
もさらに還元が進んだ１，１．１−トリフルオロエタン
が副生じ易く、その副生を抑制するために転化率を本質
的に低く抑えなければならないという重大な欠点がある
。The method of type (a) above uses palladium, rhenium,
The reaction is carried out in the presence of a reduction catalyst such as platinum at a temperature in the range of approximately 100 to 500 degrees Celsius, but even more than the target product 1,1,1,2-tetrafluoroethane. There is a serious drawback that 1,1,1-trifluoroethane, which has been reduced, is likely to be produced as a by-product, and the conversion rate must be kept essentially low in order to suppress this by-product.
さらには、上記（イ）の反応では塩化水素が必然的に副
生ずるので、触媒には耐酸性が要求される。Furthermore, since hydrogen chloride is inevitably produced as a by-product in the reaction (a) above, the catalyst is required to have acid resistance.
そのため使用触媒について種々の検討がなされてきてい
るが（例えば、特開平１−３１９４３７３１９４３８及
び−３１９４３９号公報等参照）、未だ充分とは言えな
い状況下にある。For this reason, various studies have been made regarding the catalysts to be used (see, for example, Japanese Patent Application Laid-open Nos. 1-319437319438 and 319439), but the situation is still not satisfactory.
また上記公知（ロ）のタイプの方法は、例えば無機クロ
ム化合物の存在下、はぼ３００〜５００℃程度の範囲内
の温度で反応を実施するものであるが（例えば特開昭５
５−２７１３８号公報参照）、これも転化率が低い上に
触媒寿命が短いという欠点がある。そのため、微量の酸
素を存在させて反応を実施する等の工夫がなされている
が（例えば特開昭５５−２７１３９号公報参照）、上記
欠点を充分に解消するには至っていない。さらに上記（
ロ）のタイプの方法においては、原料上の問題もある。Further, in the method of the above-mentioned known type (b), the reaction is carried out in the presence of an inorganic chromium compound at a temperature in the range of about 300 to 500°C (for example, as disclosed in Japanese Patent Application Laid-Open No.
5-27138), which also has the drawbacks of low conversion and short catalyst life. Therefore, attempts have been made to carry out the reaction in the presence of a trace amount of oxygen (see, for example, Japanese Patent Application Laid-Open No. 55-27139), but these have not yet fully overcome the above-mentioned drawbacks. Further above (
In the method of type b), there are also problems with raw materials.
すなわち、この方法に使用する１−クロロ−２，２，２
−トリフルオロエタンは、１．１゜１−トリフルオロエ
タンの塩素化によって得のであるが、反応が逐次的に進
行するため、１−クロロ−２２２−１−リフルオロエタ
ンのみを高収率で得ることは困難であり、１．１−ジク
ロロ２．２．２−トリフルオロエタン及び１．１．１ト
リクロロ−２，２，２４リフルオロエタンが副生ずると
いう問題もある。That is, the 1-chloro-2,2,2 used in this method
-Trifluoroethane can be obtained by chlorinating 1.1°1-trifluoroethane, but since the reaction proceeds sequentially, only 1-chloro-222-1-trifluoroethane can be obtained in high yield. It is difficult to obtain, and there is also the problem that 1,1-dichloro-2,2,2-trifluoroethane and 1,1,1-trichloro-2,2,24-trifluoroethane are produced as by-products.
え匪ム亘貝
本発明は、上記の如き従来法における諸欠点を解消し、
効率良く容易に１．１，１．２−テトラフルオロエタン
を製造する方法を提供することを主たる目的としている
。The present invention eliminates the various drawbacks of the conventional method as described above,
The main objective is to provide a method for efficiently and easily producing 1,1,1,2-tetrafluoroethane.
先肌ムカ１
かくして、本発明は、１，１．１−トリフルオロエタン
と臭素とを、温度５５０〜８００℃、接触時間０．５〜
１０秒の条件下で反応させることにより１−ブロモ−２
，２，２−トリフルオロエタンを得、これをフッ化水素
と反応させることを特徴とする１、１，１．２−テトラ
フルオロエタンの製造法を提供する。Tip skin irritation 1 Thus, in the present invention, 1,1.1-trifluoroethane and bromine are mixed at a temperature of 550 to 800°C and a contact time of 0.5 to 800°C.
By reacting for 10 seconds, 1-bromo-2
, 2,2-trifluoroethane is obtained, and this is reacted with hydrogen fluoride.
本発明において原料として用いる１、１．１トリフルオ
ロエタンは、例えば三フッ化クロム（ＣｒＦ３）の存在
下、２５０〜４５０℃の温度及び約１〜２０秒の接触時
間の条件下で、１．１１−トリクロロエタンとフッ化水
素とを反応させることにより高収率で得ることができ、
入手が容易である。The 1,1.1 trifluoroethane used as a raw material in the present invention is prepared, for example, in the presence of chromium trifluoride (CrF3) under conditions of a temperature of 250 to 450°C and a contact time of about 1 to 20 seconds. It can be obtained in high yield by reacting 11-trichloroethane and hydrogen fluoride,
Easy to obtain.
本発明方法においては、触媒を使用することなく、まず
１，１．１−トリクロロエタンを臭素と、５５０〜８０
０℃の温度及び０．５〜１０秒の接触時間の条件下で反
応させる。In the method of the present invention, without using a catalyst, 1,1,1-trichloroethane is first mixed with bromine and 550 to 80
The reaction is carried out under conditions of a temperature of 0° C. and a contact time of 0.5-10 seconds.
一般的には、１，１．１−トリフルオロエタンの臭素化
は逐次的に進行してモノブロム化物、ジブロム化物、ト
リブロム化物が逐次生成すると考えられ、事実、４００
〜４５０℃程度の温度でこの反応を実施すると、上記の
如き３種のブロム化物が副生ずる。Generally, bromination of 1,1,1-trifluoroethane is thought to proceed sequentially to produce monobrominated products, dibrominated products, and tribrominated products, and in fact, 400%
When this reaction is carried out at a temperature of about 450 DEG C., the three brominated products mentioned above are produced as by-products.
しかしながら、本発明者等は、驚くべきことに、１．１
．１−トリフルオロエタンと臭素とを５５０℃以上の高
い温度で反応させると、モノブロム化物、すなわち１−
ブロモ−２，２，２−トリフルオロエタンが選択的に生
成するという非常に興味ある発見をした。その反応温度
が８００℃を超えると、しかしながら熱分解反応が生ず
るようになり、所望のモノブロム化物の収率が低下し始
める。従って、本発明における１、１．１−）−リフル
オロエタンと臭素との反応は５５０〜８００℃の範囲内
の温度で実施するのが好ましい。この反応の接触時間に
ついては、０．５秒未満では未反応の臭素が生成物中に
残留するので（すなわち、反応が充分進行しないので）
好ましくなく、また１０秒を超えると熱分解が生じ始め
るので好ましくない。従って、接触時間は０．５〜１０
秒の範囲内であるのが好ましい。However, the present inventors surprisingly found that 1.1
．． When 1-trifluoroethane and bromine are reacted at a high temperature of 550°C or higher, a monobrominated product, i.e. 1-
We made the very interesting discovery that bromo-2,2,2-trifluoroethane is selectively produced. When the reaction temperature exceeds 800° C., however, thermal decomposition reactions begin to occur and the yield of the desired monobrominated product begins to decrease. Therefore, the reaction of 1,1.1-)-lifluoroethane and bromine in the present invention is preferably carried out at a temperature within the range of 550 to 800°C. Regarding the contact time of this reaction, if it is less than 0.5 seconds, unreacted bromine will remain in the product (i.e., the reaction will not proceed sufficiently).
This is not preferred, and if the time exceeds 10 seconds, thermal decomposition begins to occur, which is not preferred. Therefore, the contact time is 0.5-10
Preferably, it is within seconds.
本発明方法における１、１．１−トリフルオロエタンと
臭素の仕込量は、理論的には１：１のモル比である。実
際上は臭素を若干少なくするのが好ましいことがある（
すなわち１，１．１−トリフルオロエタン／臭素モル比
≦１であるのが好ましい）。The amounts of 1,1,1-trifluoroethane and bromine charged in the method of the present invention are theoretically in a molar ratio of 1:1. In practice, it may be preferable to slightly reduce bromine (
That is, it is preferable that the 1,1.1-trifluoroethane/bromine molar ratio is ≦1).
本発明方法では、上記のような反応によって得た１−ブ
ロモ−２，２，２−トリフルオロエタンを分離、精製し
た後、フッ化水素と反応させて、目的とする１、１，１
．２−テトラフルオロエタンを得る。この反応に使用す
る触媒としては、三フッ化クロム（Ｃｒ Ｆ ３）、ニ
フッ化鉄（ＦｅＦ２）、三フッ化アルミニウム（ｌ Ｆ
、）が好ましいものとして挙げられ、これらをアルミナ
、活性炭等に担持させるか、担持させずに使用する。さ
らには活性炭も触媒として使用することができる。この
反応は約１５０〜４００℃の範囲で実施するのが好まし
い。１５０℃未満であると反応速度が低く、また４００
℃を超えると副生物の生成が項著になり、触媒の活性劣
化も早くなる。In the method of the present invention, 1-bromo-2,2,2-trifluoroethane obtained by the above reaction is separated and purified, and then reacted with hydrogen fluoride to obtain the desired 1,1,1
．． 2-tetrafluoroethane is obtained. The catalysts used in this reaction include chromium trifluoride (CrF3), iron difluoride (FeF2), and aluminum trifluoride (lF3).
, ) are mentioned as preferable ones, and these are supported on alumina, activated carbon, etc., or used without being supported. Furthermore, activated carbon can also be used as a catalyst. Preferably, this reaction is carried out at a temperature in the range of about 150-400°C. If the temperature is less than 150°C, the reaction rate will be low;
When the temperature exceeds ℃, the formation of by-products becomes significant and the activity of the catalyst deteriorates quickly.
尚本発明方法の２工程の反応によって生じた臭化水素は
、塩素と反応させることにより容易に臭素になるので、
この臭素を第１段の工程の反応に再循環させて使用する
ことができる。Note that hydrogen bromide produced by the two-step reaction of the method of the present invention easily becomes bromine by reacting with chlorine.
This bromine can be recycled and used in the first step reaction.
以上により本発明方法では、１．１，１．２−テトラフ
ルオロエタンを効率的に、容易にかつ高収率で得ること
ができる。As described above, in the method of the present invention, 1,1,1,2-tetrafluoroethane can be obtained efficiently, easily, and in high yield.
Ｘ隻週
以下に実施例及び比較例により本発明をより具体的に説
明する。EXAMPLES The present invention will be explained in more detail below using Examples and Comparative Examples.
内径２５−一、長さ１−の石英管を反応器として使用し
、反応器出口のガス組成をガスクロマトグラフ分析した
。１，１．１−トリフルオロエタン／臭素の仕込モル比
、反応温度、接触時間、臭素転化率、１−ブロモ−２，
２，２−トリフルオロエタン選択率を第１表に示した。A quartz tube with an inner diameter of 25 mm and a length of 1 mm was used as a reactor, and the gas composition at the outlet of the reactor was analyzed by gas chromatography. 1,1.1-trifluoroethane/bromine molar ratio, reaction temperature, contact time, bromine conversion rate, 1-bromo-2,
The 2,2-trifluoroethane selectivity is shown in Table 1.
これらの結果は、２４時間にわたり１時間毎にサンプリ
ングして得た結果の平均値である。These results are averages of hourly samples over a 24 hour period.
ルＪ！ＬＬＬ二ュ
実施例１〜５で使用した反応器を用い、実施例１〜５と
同様な操作で、ただし反応条件を変えて実験を行った（
第２表参照）。その結果を第２表に示す。副生物の顕著
な生成が明らかである。Le J! Using the reactor used in LLL Du Examples 1 to 5, experiments were conducted in the same manner as in Examples 1 to 5, but with different reaction conditions (
(See Table 2). The results are shown in Table 2. Significant formation of by-products is evident.
髪！ＬＬＬ二ュ
参考のために１．１．１−トリフルオロエタンの塩素化
実験を、実施例１〜５で使用の反応器て実施した０反応
条件及び結果を第３表に示す。hair! For reference, 1.1.1-trifluoroethane chlorination experiments were conducted using the reactor used in Examples 1 to 5, and the reaction conditions and results are shown in Table 3.
火隻應６ヱ↓但
１１．１．２−テトラフルオロエタンの ゛１内径２５
Ｉ、長さ１．２＋１１の鉄製パイプを反応器とし、触媒
（第４表参照＞３００ＣＣを充填した。実施例１〜５で
得た１−ブロモ−２，２，２トリフルオロエタンを純度
９９％までに精製し、これを用いてＨＦと反応させた。11.1.2-Tetrafluoroethane ゛1 Inner diameter 25
I, an iron pipe with a length of 1.2 + 11 was used as a reactor, and a catalyst (see Table 4 > 300 CC) was filled. % and used to react with HF.
反応条件及び結果を第４表に示す。The reaction conditions and results are shown in Table 4.
手
続
補
正
書
平成２年６月ｆ日
１、事件の表示
平成２年特許願第１０８２５３号
２、発明の名称
１．１．１．２−テトラフルオロエタンの製造法３、補
正をする者
事件との関係
住所
名称 関東電化工業株式会社
４、代理人Procedural amendment dated June f, 1990 1, Indication of the case 1990 Patent Application No. 108253 2, Title of the invention 1.1.1.2 - Process for producing tetrafluoroethane 3, Person making the amendment Case and Related address name: Kanto Denka Kogyo Co., Ltd. 4, agent
Claims (1)
５５０〜８００℃、接触時間０．５〜１０秒の条件下で
反応させることにより１−ブロモ−２，２，２−トリフ
ルオロエタンを得、これをフッ化水素と反応させること
を特徴とする１，１，１，２−テトラフルオロエタンの
製造法。1-Bromo-2,2,2-trifluoro- A method for producing 1,1,1,2-tetrafluoroethane, which comprises obtaining ethane and reacting it with hydrogen fluoride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10825390A JP2739768B2 (en) | 1990-04-24 | 1990-04-24 | Method for producing 1,1,1,2-tetrafluoroethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10825390A JP2739768B2 (en) | 1990-04-24 | 1990-04-24 | Method for producing 1,1,1,2-tetrafluoroethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH045247A true JPH045247A (en) | 1992-01-09 |
| JP2739768B2 JP2739768B2 (en) | 1998-04-15 |
Family
ID=14479974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10825390A Expired - Fee Related JP2739768B2 (en) | 1990-04-24 | 1990-04-24 | Method for producing 1,1,1,2-tetrafluoroethane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2739768B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629458A (en) * | 1996-07-26 | 1997-05-13 | Alliedsignal Inc. | Process for the preparation of 2 2 2 trifluoroethanol |
| US5736012A (en) * | 1996-09-10 | 1998-04-07 | Alliedsignal Inc. | Process for the preparation of a fluorinated acid |
-
1990
- 1990-04-24 JP JP10825390A patent/JP2739768B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629458A (en) * | 1996-07-26 | 1997-05-13 | Alliedsignal Inc. | Process for the preparation of 2 2 2 trifluoroethanol |
| US5736012A (en) * | 1996-09-10 | 1998-04-07 | Alliedsignal Inc. | Process for the preparation of a fluorinated acid |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2739768B2 (en) | 1998-04-15 |
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