JP2580695B2 - Method for producing 1,1-dichloro-2,2,2-trifluoroethane - Google Patents
Method for producing 1,1-dichloro-2,2,2-trifluoroethaneInfo
- Publication number
- JP2580695B2 JP2580695B2 JP63085176A JP8517688A JP2580695B2 JP 2580695 B2 JP2580695 B2 JP 2580695B2 JP 63085176 A JP63085176 A JP 63085176A JP 8517688 A JP8517688 A JP 8517688A JP 2580695 B2 JP2580695 B2 JP 2580695B2
- Authority
- JP
- Japan
- Prior art keywords
- trifluoroethane
- dichloro
- hydrogen
- producing
- reaction
- 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 - Lifetime
Links
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
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は冷媒、トリフルオロ酢酸の原料、およびフロ
ン124（１−クロロ−1,2,2,2−テトラフルオロエタン）
の原料として有用な化合物である1,1−ジクロロ−2,2,2
−トリフルオロエタン（フロン123）の製造方法に関す
るものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a refrigerant, a raw material of trifluoroacetic acid, and Freon 124 (1-chloro-1,2,2,2-tetrafluoroethane).
1,1-dichloro-2,2,2, a compound useful as a raw material for
The present invention relates to a method for producing trifluoroethane (Freon 123).
［従来の技術および発明の課題］ 1,1,1−トリクロロ−2,2,2−トリフルオロエタン（フ
ロン113a）を還元して1,1−ジクロロ−2,2,2−トリフル
オロエタンを製造する方法としてはプロトン溶媒中で亜
鉛を還元剤として製造する方法が知られている（特開昭
58−222038を参照）。しかし、副生成物である塩化亜鉛
の処理等の問題があり、大量生産には適していない。[Problems of the Prior Art and the Invention] 1,1,1-Trichloro-2,2,2-trifluoroethane (fluorocarbon 113a) is reduced to give 1,1-dichloro-2,2,2-trifluoroethane. As a production method, there is known a method in which zinc is used as a reducing agent in a proton solvent (Japanese Patent Application Laid-Open No.
58-222038). However, there are problems such as treatment of zinc chloride which is a by-product, and it is not suitable for mass production.
［課題を解決するための手段］ 本発明は前述の課題を解決するためになされたもので
あり、1,1,1−トリクロロ−2,2,2−トリフルオロエタン
を、ルテニウムを活性成分とする水素化触媒の存在下で
水素により還元することを特徴とする1,1−ジクロロ−
2,2,2−トリフルオロエタンの製造方法である。Means for Solving the Problems The present invention has been made to solve the above-mentioned problems, and comprises 1,1,1-trichloro-2,2,2-trifluoroethane and ruthenium as active ingredients. 1,1-dichloro-reducing with hydrogen in the presence of a hydrogenation catalyst
This is a method for producing 2,2,2-trifluoroethane.
本発明において、ルテニウムを活性成分とする水素化
触媒の担体としてはアルミナ、活性炭が好適である。な
お、水素化触媒の使用に当たってはルテニウムの少なく
とも一部を還元することが好適である。In the present invention, alumina and activated carbon are suitable as a carrier for a hydrogenation catalyst containing ruthenium as an active component. In using a hydrogenation catalyst, it is preferable to reduce at least a part of ruthenium.
水素と原料フロン113aの割合は大幅に変動させ得る。
しかしながら、通常、化学量論量の水素を使用してハロ
ゲン原子を除去する。原料フロン113aの全モル数に対し
て、化学量論量よりかなり多い量、例えば４モルまたは
それ以上の水素を使用し得る。反応圧力については常
圧、または常圧以上の圧力が使用し得る。The ratio between the hydrogen and the raw material chlorofluorocarbon 113a can be largely varied.
However, usually a stoichiometric amount of hydrogen is used to remove the halogen atoms. Substantially more than the stoichiometric amount, for example 4 moles or more, of hydrogen can be used based on the total number of moles of the raw material fluorocarbon 113a. The reaction pressure may be normal pressure or a pressure higher than normal pressure.
反応温度は０℃〜450℃、好ましくは50℃〜300℃と
し、液相、または気相で反応を行なうことが適当であ
る。The reaction temperature is 0 ° C. to 450 ° C., preferably 50 ° C. to 300 ° C., and the reaction is suitably performed in a liquid phase or a gas phase.
接触時間は、反応を気相で行なう場合には通常0.1〜3
00秒、特には５〜30秒である。The contact time is usually 0.1 to 3 when the reaction is carried out in the gas phase.
00 seconds, especially 5 to 30 seconds.
［実施例］ 以下に本発明の実施例を示す。[Example] An example of the present invention will be described below.
調理例 活性炭を純水中に浸漬し細孔内部まで水を含浸させ
た。塩酸を用いてpHを調整した後、塩化ルテニウムを活
性炭の重量に対し金属成分の全重量で0.5重量％だけ溶
解した水溶液を少しずつ滴下しイオン成分を活性炭に吸
着させた。純水を用いて洗浄した後、それを150℃で５
時間乾燥した。次に窒素中550℃で４時間乾燥した後、
水素を導入し、５時間,300℃に保持して還元した。Cooking example Activated carbon was immersed in pure water to impregnate water into the pores. After adjusting the pH using hydrochloric acid, an aqueous solution in which ruthenium chloride was dissolved by 0.5% by weight based on the total weight of the metal component with respect to the weight of the activated carbon was added dropwise little by little, and the ionic component was adsorbed on the activated carbon. After washing with pure water, it is
Dried for hours. Next, after drying in nitrogen at 550 ° C for 4 hours,
Hydrogen was introduced and reduced at 300 ° C. for 5 hours.
実施例 １ 調製例のようにして調製した触媒を300cc充填した内
径2.6cm、長さ100cmのインコネル600製反応管を塩浴炉
中に浸漬した。Example 1 A reaction tube made of Inconel 600 having an inner diameter of 2.6 cm and a length of 100 cm filled with 300 cc of the catalyst prepared as in the preparation example was immersed in a salt bath furnace.
水素とフロン−113aを1:1のモル比で反応管に導入し
た。水素、フロン113aの流量はそれぞれ、100cc/分、10
0cc/分とした。反応温度は120℃とした。生成ガスの分
析にはガスクロを用いた。その結果を第１表No.1に示
す。Hydrogen and Freon-113a were introduced into the reaction tube at a molar ratio of 1: 1. The flow rates of hydrogen and Freon 113a were 100 cc / min and 10
0 cc / min. The reaction temperature was 120 ° C. Gas chromatography was used for the analysis of the produced gas. The results are shown in Table 1 No. 1.
実施例２ 反応温度を200℃とする他は実施例１と同様にして反
応を行ない生成ガスを分析した。結果を第１表No.2に示
す。Example 2 A reaction was carried out in the same manner as in Example 1 except that the reaction temperature was changed to 200 ° C., and the produced gas was analyzed. The results are shown in Table 1 No. 2.
実施例３ 担体をアルミナとする他は調製例と同様にしてルテニ
ウム触媒を調製し、実施例１同様に反応を行ない生成ガ
スの分析を行なった。結果を第１表No.3に示す。なお、
第１表中の％はすべてモル％を表す。Example 3 A ruthenium catalyst was prepared in the same manner as in the preparation example except that alumina was used as the carrier, and the reaction was carried out in the same manner as in example 1 to analyze the generated gas. The results are shown in Table 1 No. 3. In addition,
All percentages in Table 1 represent mol%.
［発明の効果］ 本発明は、実施例に示すように、フロン113a（1,1,1
−トリクロロ−2,2,2−トリフルオロエタン）を出発物
質として、円滑有利に良好な収率でフロン123（1,1−ジ
クロロ−2,2,2−トリフルオロエタン）を製造し得ると
いう効果を有する。 [Effects of the Invention] The present invention provides, as shown in the examples, Freon 113a (1,1,1
Starting from trichloro-2,2,2-trifluoroethane), it is possible to produce Freon 123 (1,1-dichloro-2,2,2-trifluoroethane) smoothly and advantageously in good yield. Has an effect.
Claims (4)
タンを、ルテニウムを活性成分とする水酸化触媒の存在
下で水素により還元することを特徴とする1,1−ジクロ
ロ−2,2,2−トリフルオロエタンの製造方法。1. A method for reducing 1,1,1-dichloro-2,2,2-trifluoroethane with hydrogen in the presence of a hydroxylation catalyst containing ruthenium as an active component. A method for producing dichloro-2,2,2-trifluoroethane.
タンに対して少なくとも化学量論量の水素を使用する請
求項１に記載の製造方法。2. The process according to claim 1, wherein at least a stoichiometric amount of hydrogen is used relative to 1,1,1-trilo-2,2,2-trifluoroethane.
担体上に担持されている水素化触媒を用いる請求項１ま
たは２に記載の製造方法。3. The production method according to claim 1, wherein a hydrogenation catalyst in which ruthenium is supported on an activated carbon carrier or an alumina carrier is used.
450℃の温度範囲で行なう請求項１、２または３に記載
の製造方法。4. The reaction is carried out at 0 ° C. in a liquid phase or a gas phase.
The method according to claim 1, 2 or 3, wherein the method is carried out in a temperature range of 450 ° C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63085176A JP2580695B2 (en) | 1988-04-08 | 1988-04-08 | Method for producing 1,1-dichloro-2,2,2-trifluoroethane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63085176A JP2580695B2 (en) | 1988-04-08 | 1988-04-08 | Method for producing 1,1-dichloro-2,2,2-trifluoroethane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01258631A JPH01258631A (en) | 1989-10-16 |
| JP2580695B2 true JP2580695B2 (en) | 1997-02-12 |
Family
ID=13851351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63085176A Expired - Lifetime JP2580695B2 (en) | 1988-04-08 | 1988-04-08 | Method for producing 1,1-dichloro-2,2,2-trifluoroethane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2580695B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2641780B1 (en) * | 1989-01-19 | 1991-04-19 | Atochem | SELECTIVE HYDROGENOLYSIS OF PERHALOGENATED ETHANE DERIVATIVES |
| JP3031508B2 (en) * | 1992-05-19 | 2000-04-10 | エイ・ジー・テクノロジー株式会社 | Reduction method of polychlorinated alkanes |
-
1988
- 1988-04-08 JP JP63085176A patent/JP2580695B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01258631A (en) | 1989-10-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5447896A (en) | Hydrodehalogenation catalysts and their preparation and use | |
| US5136113A (en) | Catalytic hydrogenolysis | |
| US5545774A (en) | Process for the manufacture of 1,1,1,3,3,3-hexafluoropropane | |
| US5523501A (en) | Catalytic hydrogenolysis | |
| JP2580695B2 (en) | Method for producing 1,1-dichloro-2,2,2-trifluoroethane | |
| JPH0399026A (en) | Production of pentafluoroethane | |
| WO1993009080A1 (en) | Process for producing 1,1-dichloro-2,2,2-trifluoroethane | |
| US6218587B1 (en) | Catalytic hydrogenolysis | |
| JPH01319441A (en) | Production of 1,1-dichloro-2,2,2-trifluoroethane | |
| JP2531215B2 (en) | Method for producing tetrafluoroethane | |
| JPH0655683B2 (en) | Method for producing 1,2-dichlorobenzene | |
| JP2581170B2 (en) | Method for producing 1,1-dichloro-2,2,2-trifluoroethane | |
| JP2712475B2 (en) | Method for producing propane having difluoromethylene group | |
| JP2580696B2 (en) | Method for producing pentafluoroethane | |
| JPH06279328A (en) | Production of hexafluoropropane | |
| KR930000889B1 (en) | Process for the selective hydrogenolysis of perhalogeno-ethanes | |
| JPH01132537A (en) | Production of tetrafluoroethane | |
| JPH07138194A (en) | Production of 1,1,1,3,3-pentafluoropropane | |
| JP2760136B2 (en) | Production method of hydrogen-containing chlorofluorocarbons | |
| JPH01242536A (en) | Production of tetrafluoroethane | |
| JP2586129B2 (en) | Method for producing 1,1,1,2-tetrafluoroethane | |
| JPH01132538A (en) | Production of tetrafluoroethane | |
| JPH02218625A (en) | Production of hcfc-134a | |
| JP2581169B2 (en) | Method for producing R-134a | |
| JP2551051B2 (en) | Method for producing 1,1,1,2-tetrafluoroethane |