JPS6296442A - Novel fluorine-containing compound and production thereof - Google Patents
Novel fluorine-containing compound and production thereofInfo
- Publication number
- JPS6296442A JPS6296442A JP60235965A JP23596585A JPS6296442A JP S6296442 A JPS6296442 A JP S6296442A JP 60235965 A JP60235965 A JP 60235965A JP 23596585 A JP23596585 A JP 23596585A JP S6296442 A JPS6296442 A JP S6296442A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- containing compound
- novel fluorine
- monochloromethoxy
- formula
- 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
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、新規含フッ素化合物及びその製法に関する。[Detailed description of the invention] [Industrial application field] The present invention relates to a novel fluorine-containing compound and a method for producing the same.
本発明の新規含フッ素化合物、すなわち１−モノクロロ
メトキシ−１−フルオロ−２〜トリフルオロメチル−３
，３，３−１−リフルオロプロペンは、これを酢酸カリ
ウム等と反応させることにより分子内脱炭酸して容易に
２−トリフルオロメチル−３，３，３−トリフルオロプ
ロペンに導くことができる。Novel fluorine-containing compounds of the present invention, namely 1-monochloromethoxy-1-fluoro-2 to trifluoromethyl-3
, 3,3-1-lifluoropropene can be easily led to 2-trifluoromethyl-3,3,3-trifluoropropene by intramolecular decarboxylation by reacting it with potassium acetate etc. .
この２−トリフルオロメチル−３，３，３−’Ｉ−リリ
フルオロプロペンは、ビニリデンフルオライドの共単量
体として耐熱性のきわめて優れたビニリデンフルオライ
ド／２−トリフルオロメチル−３゜３．３−）リフルオ
ロプロペン交互共重合体を与えることができ（特公昭５
９−２８２１０号公報参照）、さらにエチレン／テトラ
フルオロエチレン共重合体の改質用単量体として共重合
体に少量添加することにより該重合体の物性を著しく改
善することができる（特公昭５９＝２５８０６号公報参
照）ことが知られており、重合体の単量体としてきわめ
て有用な化合物である。This 2-trifluoromethyl-3,3,3-'I-lylifluoropropene is a vinylidene fluoride/2-trifluoromethyl-3.3. 3-) Lifluoropropene alternating copolymer can be obtained (Japanese Patent Publication No. 5
9-28210), and by adding a small amount to the ethylene/tetrafluoroethylene copolymer as a modifying monomer, the physical properties of the polymer can be significantly improved (Japanese Patent Publication No. 59 = 25806), and is an extremely useful compound as a monomer for polymers.
このように、本発明の新規含フッ素化合物は、前記重合
体の屯量体である２−トリフルオロメチル−３，３，３
−１−リフルオロプロペンの合成中間体として有用であ
る。Thus, the novel fluorine-containing compound of the present invention is a monomer of the above polymer, 2-trifluoromethyl-3,3,3
It is useful as a synthetic intermediate for -1-lifluoropropene.
本発明の含フッ素化合物は、従来知られていない。 The fluorine-containing compound of the present invention has not been previously known.
本発明の目的は、２−１−リフル第１１メチル−３゜３
．３−１−ＩＪフルオロプロペンの中間体としてイｉ用
な新規含フッ素化合物及びその製法を提供することにあ
る。The object of the present invention is to obtain 2-1-rifle 11th methyl-3゜3
．． An object of the present invention is to provide a novel fluorine-containing compound useful as an intermediate for 3-1-IJ fluoropropene and a method for producing the same.
本発明の要旨は、式
％式％（）
で示される新規含フッ素化合物、及び１−モノクロロメ
トキシ−１，１−ジフルオ［１−２−トリフルオロメチ
ル−３，３，３−トリフルオロプロパンをアルカリ水溶
液中で脱フッ化水素さゼることを特徴とする式（１）で
示される新規含フッ素化合物の製法に存する。The gist of the present invention is to provide a novel fluorine-containing compound represented by the formula % and 1-monochloromethoxy-1,1-difluoro[1-2-trifluoromethyl-3,3,3-trifluoropropane The present invention relates to a method for producing a novel fluorine-containing compound represented by formula (1), which comprises dehydrofluorination in an alkaline aqueous solution.
本発明の新規含フッ素化合物ずなわら（１）式で示され
る１−モノクロロメトキン−１−フルオロ−２−トリフ
ルオロメチル−３，３，３−）リフルオロプロペンは、
１−モノクロロメトキシ−１゜１−ジフルオロ−２−ト
リフルオＩ′Ｊメチル−３，３゜３−トリフルオロプロ
パンをアルカリ水溶液中で脱フッ化水素させることによ
って次式のように得られる。The novel fluorine-containing compound of the present invention Zunawara 1-monochloromethyne-1-fluoro-2-trifluoromethyl-3,3,3-)lifluoropropene represented by formula (1) is
The following formula is obtained by dehydrofluorinating 1-monochloromethoxy-1°1-difluoro-2-trifluoroI'J methyl-3,3°3-trifluoropropane in an aqueous alkaline solution.
ＨＦ
（ＣＦ ４１）２ＣＨＣＦ ２０ ＣＨ２Ｃｌ２−→（
ＣＦ、１）ｚＣ＝ＣＦＯＣＨｚＣｐ
本発明の原料である１−モノクロロメトキシ−１゜１−
ジフルオロ−２−トリフルオロメチル−３，３゜３−ト
リフルオロプロパンは、例えば１−メトキシ−１，１−
ジフルオロ−２−トリフルオロメチル−３，３，３−ト
リフルオロプロパンを光塩素化するごとにより得られる
。HF (CF 41)2CHCF 20 CH2Cl2−→(
CF, 1)zC=CFOCHzCp 1-monochloromethoxy-1゜1- which is the raw material of the present invention
Difluoro-2-trifluoromethyl-3,3゜3-trifluoropropane is, for example, 1-methoxy-1,1-
It is obtained by photochlorinating difluoro-2-trifluoromethyl-3,3,3-trifluoropropane.
本発明に使用するアルカリとしては、水酸化ナトリウム
、水酸化カリウム等のアルカリ金属水酸化物が好ましく
、その使用量は、１−モノクロロメトキシ−１，１−ジ
フルオロ−２−トリフルオロメチル−３，３，３−）リ
フルオロプロパン１モルに対して１〜５モルが好ましい
。溶媒としては、通常水を用いる。The alkali used in the present invention is preferably an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, and the amount used is 1-monochloromethoxy-1,1-difluoro-2-trifluoromethyl-3, The amount is preferably 1 to 5 mol per 1 mol of 3,3-)lifluoropropane. Water is usually used as the solvent.
前記の脱フッ化水素反応は、相間移動触媒を使用するこ
とにより、より温和な反応条件で円滑に行うことができ
る。相間移動触媒としては、第４アンモニウム化合物、
第４ホスホニウム化合物、クラウンエーテル化合物、ス
ルホニウム化合物等が使用できる。就中、性能及び価格
の面から第４アンモニウム化合物及び第４ホスホニウム
化合物が好ましい。用いられる代表的な相間移動触媒は
、第４アンモニウム化合物であれば、テトラメチルアン
モニウムクロライド、ヘンシルトリメチルアンモニウム
クロライド、テトラブチルアンモニウムブロマイド、テ
トラブチルアンモニウムクロライド等、第４ホスホニウ
ム化合物であれば、トリフェニルメチルホスホニウムナ
イトレート、トリフェニルエチルホスホニウムクロライ
ド、トリフェニルエチルホスホニウムブロマイド、ヘン
シルトリフェニルホスホニウムクロライド等である。The dehydrofluorination reaction described above can be carried out smoothly under milder reaction conditions by using a phase transfer catalyst. As the phase transfer catalyst, quaternary ammonium compounds,
Quaternary phosphonium compounds, crown ether compounds, sulfonium compounds, etc. can be used. Among these, quaternary ammonium compounds and quaternary phosphonium compounds are preferred in terms of performance and cost. Typical phase transfer catalysts used include quaternary ammonium compounds such as tetramethylammonium chloride, hensyltrimethylammonium chloride, tetrabutylammonium bromide, and tetrabutylammonium chloride; quaternary phosphonium compounds such as triphenyl These include methylphosphonium nitrate, triphenylethylphosphonium chloride, triphenylethylphosphonium bromide, hensyltriphenylphosphonium chloride, and the like.
これらの相間移動触媒の使用量は、１−モノクロロメト
キシ−Ｉｌｌ−ジフルオロ−２−トリフルオロメチル−
３，３，３−）リフルオロプロパン１モルに対して通常
０．００１〜０．２モルである。The amount of these phase transfer catalysts used is 1-monochloromethoxy-Ill-difluoro-2-trifluoromethyl-
The amount is usually 0.001 to 0.2 mol per 1 mol of 3,3,3-)rifluoropropane.
反応温度は、１０〜１００°Ｃ１好ましくは２０〜５０
℃、反応時間は、０．５〜１０時間、好ましくは１〜４
時間である。The reaction temperature is 10 to 100°C, preferably 20 to 50°C.
°C, reaction time is 0.5 to 10 hours, preferably 1 to 4 hours.
It's time.
以下に実施例を示し、本発明を更に詳しく説明する。 EXAMPLES The present invention will be explained in more detail with reference to Examples below.
実施例１
温度計、コンデンサー及び滴下漏斗を備えた１０１００
Ｏ！四つロフラスコに、水酸化カリウム８０．０ｇ （
１，４３モル）、水３００ｇ及びテトラブチルアンモニ
ウムブロマイド２ 、０ ｇ ヲ仕込んだ。系内の温度
１０’Ｃで、■−モノクロロメトキシー１．１−ジフル
オロ−２−トリフルオロメチル−３，３，１＋−リフル
オロプロパン２３４ｇ（８７８ミリモル）を滴下した。Example 1 10100 with thermometer, condenser and addition funnel
O! 80.0 g of potassium hydroxide (
1.43 mol), 300 g of water, and 2.0 g of tetrabutylammonium bromide were charged. At a system temperature of 10'C, 234 g (878 mmol) of -monochloromethoxy-1,1-difluoro-2-trifluoromethyl-3,3,1+-lifluoropropane was added dropwise.
滴下終了後、攪拌しながら４０゛Ｃで２Ｉ１．１１間反
応さ−１た。反応終了後、有機層を分則し、２００１Ｎ
の水で３回洗った後、藤留により１−モノクｌ目７メト
キシー１−フルオロ−２−トリフル第１′、Ｉメチル−
３、３、３−トリフルオロプロペン１８５ｇ （７５１
ミ’Ｊモル）を得た。収率８５．５％、沸点１１８℃。After the addition was completed, the reaction was carried out at 40°C for 1.11 hours with stirring. After the reaction, separate the organic layer and add 2001N
After washing three times with water of
3,3,3-trifluoropropene 185g (751
Mi'Jmol) was obtained. Yield 85.5%, boiling point 118°C.
実施例２
温度計、コンテン１ノー及び滴下漏斗を備えた１０００
ｍ７！四つ目フラスコに、水酸化ナトリウム５０ｇ （
１，２５モル）及び水３００ｇを仕込んだ。Example 2 1000 with thermometer, content 1 no and dropping funnel
m7! In a fourth flask, add 50 g of sodium hydroxide (
1.25 mol) and 300 g of water were charged.
系内の温度１０℃で、１−モノクロロメトキシ−１、】
−ジフルオロ−２−■・リフルオロメチル−３，３，３
−トリフルオロプロパン２３４ｇ （８７８ミリモル
）を滴下した。滴下終了後、攪拌しながら６０℃で５時
間反応させた。反応終了後、有機層を分離し、２００ｇ
の水で３回洗った後、蒸留により１−モノクロコメ１−
キシ−１−フルオロ＝２−トリフルオロメチル−３，３
，３−）リフルオロプロペン１５５ｇ （６２９ミリモ
ル）ヲ得た。At a system temperature of 10°C, 1-monochloromethoxy-1,]
-difluoro-2-■・lifluoromethyl-3,3,3
-234 g (878 mmol) of trifluoropropane were added dropwise. After the dropwise addition was completed, the mixture was reacted at 60° C. for 5 hours with stirring. After the reaction was completed, the organic layer was separated and 200 g
After washing three times with water, 1-monochrome rice 1-
xy-1-fluoro=2-trifluoromethyl-3,3
,3-)lifluoropropene (155 g (629 mmol)) was obtained.
収率７１．６％。Yield 71.6%.
本発明によれば、２−トリフルオロメチル−３゜３．３
−１−リフルオロプロペンの合成中間体として有用な新
規含フッ素化合物を容易に提供することができる。According to the invention, 2-trifluoromethyl-3°3.3
A novel fluorine-containing compound useful as a synthetic intermediate for -1-lifluoropropene can be easily provided.
以上 特許出願人 ダイキン工業株式会社that's all Patent applicant: Daikin Industries, Ltd.
Claims (1)
れる新規含フッ素化合物。 ２、１−モノクロロメトキシ−１，１−ジフルオロ−２
−トリフルオロメチル−３，３，３−トリフルオロプロ
パンをアルカリ水溶液中で脱フッ化水素させることを特
徴とする式 （ＣＦ＿３）＿２Ｃ＝ＣＦＯＣＨ＿２Ｃｌ で示される新規含フッ素化合物の製法。 ３、相間移動触媒を使用する特許請求の範囲第２項記載
の製法。 ４、相間移動触媒が第４アンモニウム化合物又は第４ホ
スホニウム化合物である特許請求の範囲第３項記載の製
法。[Claims] 1. A novel fluorine-containing compound represented by the formula (CF_3)_2C=CFOCH_2Cl. 2,1-monochloromethoxy-1,1-difluoro-2
A method for producing a novel fluorine-containing compound represented by the formula (CF_3)_2C=CFOCH_2Cl, which comprises dehydrofluorinating -trifluoromethyl-3,3,3-trifluoropropane in an alkaline aqueous solution. 3. The production method according to claim 2, which uses a phase transfer catalyst. 4. The production method according to claim 3, wherein the phase transfer catalyst is a quaternary ammonium compound or a quaternary phosphonium compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60235965A JPS6296442A (en) | 1985-10-21 | 1985-10-21 | Novel fluorine-containing compound and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60235965A JPS6296442A (en) | 1985-10-21 | 1985-10-21 | Novel fluorine-containing compound and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6296442A true JPS6296442A (en) | 1987-05-02 |
| JPH0329775B2 JPH0329775B2 (en) | 1991-04-25 |
Family
ID=16993833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60235965A Granted JPS6296442A (en) | 1985-10-21 | 1985-10-21 | Novel fluorine-containing compound and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6296442A (en) |
-
1985
- 1985-10-21 JP JP60235965A patent/JPS6296442A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0329775B2 (en) | 1991-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |