JPH0749391B2 - Fluorine-containing compound and method for producing the same - Google Patents
Fluorine-containing compound and method for producing the sameInfo
- Publication number
- JPH0749391B2 JPH0749391B2 JP62140570A JP14057087A JPH0749391B2 JP H0749391 B2 JPH0749391 B2 JP H0749391B2 JP 62140570 A JP62140570 A JP 62140570A JP 14057087 A JP14057087 A JP 14057087A JP H0749391 B2 JPH0749391 B2 JP H0749391B2
- Authority
- JP
- Japan
- Prior art keywords
- containing compound
- tetrafluoropropanoate
- hexafluoropropane
- mol
- same
- 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 - Fee Related
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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)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、新規含フツ素化合物及びその製法に関する。
本発明の新規含フツ素化合物、就中2,3,3,3−テトラフ
ルオロプロパン酸モノクロロメチルは、アミンと反応さ
せることにより容易に2,3,3,3−テトラフルオロプロペ
ンに導くことができる。The present invention relates to a novel fluorine-containing compound and a method for producing the same.
The novel fluorine-containing compound of the present invention, especially monochloromethyl 2,3,3,3-tetrafluoropropanoate, can be easily converted to 2,3,3,3-tetrafluoropropene by reacting with an amine. it can.
2,3,3,3−テトラフルオロプロペンは、テトラフルオロ
エチレン、トリフルオロエチレン、ビニリデンフルオラ
イド等の共重合単量体として有用である。又、2,3,3,3
−テトラフルオロプロペンは、例えばエチレン／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高温での強度、
耐クラツク性等を著しく改善することができ、改質用単
量体としても有用な化合物である。2,3,3,3-Tetrafluoropropene is useful as a copolymerization monomer of tetrafluoroethylene, trifluoroethylene, vinylidene fluoride and the like. Also, 2, 3, 3, 3
-Tetrafluoropropene is, for example, the strength of the polymer at high temperature by adding a small amount to the copolymer as a monomer for modifying the ethylene / tetrafluoroethylene copolymer,
It is a compound which can remarkably improve the crack resistance and is also useful as a modifying monomer.
このように、本発明の新規含フツ素化合物、就中2,3,3,
3−テトラフルオロプロパン酸モノクロロメチルは、2,
3,3,3−テトラ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, especially 2,3,3,
Monochloromethyl 3-tetrafluoropropanoate is 2,
It is useful as a synthetic intermediate for 3,3,3-tetrafluoropropene.
本発明の含フツ素化合物は、従来知られていない。 The fluorine-containing compound of the present invention has not hitherto been known.
本発明の目的は、2,3,3,3−テトラフルオロプロペンの
中間体として有用な新規含フツ素化合物及びその製法を
提供することにある。An object of the present invention is to provide a novel fluorine-containing compound useful as an intermediate for 2,3,3,3-tetrafluoropropene and a method for producing the same.
本発明の要旨は、一般式 CF3CHFCO2CClX1X2 （Ｉ） 〔式中、X1及びX2は同一又は相異なり、水素原子又は塩
素原子を表す。〕 で示される新規含フツ素化合物、及び2,3,3,3−テトラ
フルオロプロパン酸メチルを光の照射下に塩素と接触さ
せることを特徴とする一般式（Ｉ）で示される新規含フ
ツ素化合物の製法、及び１−モノクロロメトキシ−1,1,
2,3,3,3−ヘキサフルオロプロパンを酸触媒存在下で加
水分解することを特徴とする2,3,3,3−テトラフルオロ
プロパン酸モノクロロメチルの製法に存する。The gist of the present invention is the general formula CF 3 CHFCO 2 CClX 1 X 2 (I) [wherein, X 1 and X 2 are the same or different and represent a hydrogen atom or a chlorine atom. ] And a novel fluorine-containing compound represented by the general formula (I), characterized in that methyl 2,3,3,3-tetrafluoropropanoate is brought into contact with chlorine under irradiation of light. Process for producing elementary compound, and 1-monochloromethoxy-1,1,
A method for producing monochloromethyl 2,3,3,3-tetrafluoropropanoate, which comprises hydrolyzing 2,3,3,3-hexafluoropropane in the presence of an acid catalyst.
本発明の新規含フツ素化合物は、一般式（Ｉ）で示され
るが、具体的には、2,3,3,3−テトラフルオロプロパン
酸モノクロロメチル、2,3,3,3−テトラフルオロプロパ
ン酸ジクロロメチル及び2,3,3,3−テトラフルオロプロ
パン酸トリクロロメチルである。The novel fluorine-containing compound of the present invention is represented by the general formula (I), and specifically, monochloromethyl 2,3,3,3-tetrafluoropropanoate, 2,3,3,3-tetrafluoro These are dichloromethyl propanoate and trichloromethyl 2,3,3,3-tetrafluoropropanoate.
本発明の新規含フツ素化合物は、2,3,3,3−テトラフル
フルオロプロパン酸メチルを光の照射下に塩素と接触さ
せることにより得られる。原料である2,3,3,3−テトラ
フルオロプロパン酸メチルは、例えば１−メトキシ−1,
1,2,3,3,3−ヘキサフルオロプロパンを酸触媒の存在下
に加水分解することにより得られる。The novel fluorine-containing compound of the present invention can be obtained by contacting methyl 2,3,3,3-tetrafluorofluoropropanoate with chlorine under irradiation of light. Starting material methyl 2,3,3,3-tetrafluoropropanoate is, for example, 1-methoxy-1,
It is obtained by hydrolyzing 1,2,3,3,3-hexafluoropropane in the presence of an acid catalyst.
本発明の前記光塩素化反応は、気相又は液相で行うこと
ができる。光塩素化反応の際の光源は、492nm以下の波
長の光を発するもの、具体的には水銀灯、キセノン灯等
が好ましい。光反応槽の材質としては、パイレツクス、
コアレツクス、石英、サプラシル等が使用可能である。
反応温度は、通常０〜400℃、好ましくは20〜150℃であ
る。圧力は常圧乃至少加圧が採用される。The photochlorination reaction of the present invention can be carried out in a gas phase or a liquid phase. The light source used in the photochlorination reaction is preferably one that emits light having a wavelength of 492 nm or less, specifically, a mercury lamp, a xenon lamp or the like. As the material of the photoreactor,
Coalex, quartz, suprasil, etc. can be used.
The reaction temperature is generally 0 to 400 ° C, preferably 20 to 150 ° C. Normal pressure or low pressurization is adopted as the pressure.
また、本発明の新規含フツ素化合物のうちのひとつであ
る2,3,3,3−テトラフルオロプロパン酸モノクロロメチ
ルは、１−モノクロロメトキシ−1,1,2,2,3,3,3−ヘキ
サフルオロプロパンを酸触媒存在下で加水分解すること
によっても得られる。原料である１−モノクロロメトキ
シ−1,1,2,3,3,3−ヘキサフルオロプロパンは、例えば
１−メトキシ−1,1,2,3,3,3−ヘキサフルオロプロパン
を光塩素化することにより得られる。In addition, one of the novel fluorine-containing compounds of the present invention, monochloromethyl 2,3,3,3-tetrafluoropropanoate is 1-monochloromethoxy-1,1,2,2,3,3,3. It can also be obtained by hydrolyzing hexafluoropropane in the presence of an acid catalyst. The starting material, 1-monochloromethoxy-1,1,2,3,3,3-hexafluoropropane, for example, photochlorinates 1-methoxy-1,1,2,3,3,3-hexafluoropropane. It is obtained by
本発明の前記加水分解反応は、通常、水の存在下、酸触
媒を使用して行われる。水の量は、１−モノクロロメト
キシ−1,1,2,3,3,3−ヘキサフルオロプロパン１モルに
対して１〜10モルが好ましい。あるいは、水のかわりに
二酸化ケイ素等の酸化物を使用してもよい。酸触媒とし
ては、硫酸、フルオロ硫酸、トリフルオロメタンスルホ
ン酸等が好ましい。酸触媒の使用量は、１−モノクロロ
メトキシ−1,1,2,3,3,3−ヘキサフルオロプロパン１モ
ルに対して0.0001〜２モルが好ましい。反応温度は通常
20〜200℃、反応時間は通常0.5〜50時間である。The hydrolysis reaction of the present invention is usually carried out in the presence of water using an acid catalyst. The amount of water is preferably 1 to 10 mol per 1 mol of 1-monochloromethoxy-1,1,2,3,3,3-hexafluoropropane. Alternatively, an oxide such as silicon dioxide may be used instead of water. As the acid catalyst, sulfuric acid, fluorosulfuric acid, trifluoromethanesulfonic acid and the like are preferable. The amount of the acid catalyst used is preferably 0.0001 to 2 mol per 1 mol of 1-monochloromethoxy-1,1,2,3,3,3-hexafluoropropane. Reaction temperature is normal
The reaction time is usually 20 to 200 ° C. and 0.5 to 50 hours.
以下、本発明を参考例及び実施例によって更に具体的に
説明する。Hereinafter, the present invention will be described in more detail with reference to Examples and Examples.
参考例１ 温度計、コンデンサー及び撹拌機を備えた１四つ口フ
ラスコに、二酸化ケイ素36.0g（0.60モル）及び濃硫酸6
0.0g（0.61モル）を仕込み、系内を温度50℃に加熱し
て、１−メトキシ−1,1,2,3,3,3−ヘキサフルオロプロ
パン182g（1.0モル）を滴下した。滴下終了後、２時間
後撹拌した。反応が終了した後、蒸留によって2,3,3,3
−テトラフルオロプロパン酸メチル144g（収率90％）を
得た。沸点96℃。Reference Example 1 A single four-necked flask equipped with a thermometer, a condenser and a stirrer was charged with 36.0 g (0.60 mol) of silicon dioxide and 6 parts of concentrated sulfuric acid.
0.0 g (0.61 mol) was charged, the system was heated to a temperature of 50 ° C., and 182 g (1.0 mol) of 1-methoxy-1,1,2,3,3,3-hexafluoropropane was added dropwise. After completion of dropping, the mixture was stirred for 2 hours. After the reaction is complete, distill it to 2,3,3,3
-144 g of methyl tetrafluoropropanoate (90% yield) were obtained. Boiling point 96 ° C.
参考例２ 温度計、コンデンサー及び塩素導入管を備えた500ml四
つ口フラスコ（パイレツクス製）に、１−メトキシ−1,
1,2,3,3,3−ヘキサフルオロプロパン600g（3.30モル）
を仕込んだ。75ワツト高圧水銀灯照射下、塩素導入管よ
り塩素を112cc/min（５ミリモル/min）の割合で前記フ
ラスコ内に送り込み、45℃で７時間反応させた。反応終
了後蒸留により、１−モノクロロメトキシ−1,1,2,3,3,
3−ヘキサフルオロプロパン314g（沸点87℃）及び１−
ジクロロメトキシ−1,1,2,3,3,3−ヘキサフルオロプロ
パン28g（沸点95℃）を得た。なお、同時に未反応の１
−メトキシ−1,1,2,3,3,3−ヘキサフルオロプロパン25g
を回収した。Reference Example 2 In a 500 ml four-necked flask (made by Pyrex) equipped with a thermometer, a condenser and a chlorine introduction tube, 1-methoxy-1,
1,2,3,3,3-hexafluoropropane 600 g (3.30 mol)
Was charged. Under irradiation with a 75-watt high-pressure mercury lamp, chlorine was fed into the flask at a rate of 112 cc / min (5 mmol / min) through a chlorine introduction tube and reacted at 45 ° C. for 7 hours. After completion of the reaction, by distillation, 1-monochloromethoxy-1,1,2,3,3,
314 g of 3-hexafluoropropane (boiling point 87 ° C) and 1-
28 g of dichloromethoxy-1,1,2,3,3,3-hexafluoropropane (boiling point 95 ° C) was obtained. In addition, unreacted 1 at the same time
-Methoxy-1,1,2,3,3,3-hexafluoropropane 25 g
Was recovered.
実施例１ 温度計、コンデンサー及び塩素導入管を備えた500ml四
つ口フラスコ（パイレツクス製）に、参考例１で得た2,
3,3,3−テトラフルオロプロパン酸メチル544g（3.40モ
ル）を仕込んだ。次に75ワツト高圧水銀灯照射下、塩素
導入管より塩素を224cc/min（10ミリモル/min）の割合
で、前記フラスコ内に送り込み、50℃で12時間反応させ
た。反応終了後蒸留により、2,3,3,3−テトラフルオロ
プロパン酸モノクロロメチル68g（沸点125℃）、2,3,3,
3−テトラフルオロプロパン酸ジクロロメチル460g（沸
点132℃）、2,3,3,3−テトラフルオロプロパン酸トリク
ロロメチル105g（沸点152℃）を得た。Example 1 A 500 ml four-necked flask (manufactured by Pyrex) equipped with a thermometer, a condenser, and a chlorine inlet tube was used to obtain 2, 2.
544 g (3.40 mol) of methyl 3,3,3-tetrafluoropropanoate was charged. Then, under irradiation with a 75-watt high-pressure mercury lamp, chlorine was fed into the flask at a rate of 224 cc / min (10 mmol / min) from a chlorine introducing tube and reacted at 50 ° C. for 12 hours. After completion of the reaction, by distillation, 2,3,3,3-tetrafluoropropanoic acid monochloromethyl 68 g (boiling point 125 ° C.), 2,3,3,
460 g of dichloromethyl 3-tetrafluoropropanoate (boiling point 132 ° C.) and 105 g of trichloromethyl 2,3,3,3-tetrafluoropropanoate (boiling point 152 ° C.) were obtained.
元素分析（％） C4H3F4O2Clとして 計算値 実測値 Ｃ 24.68 24.45 Ｈ 1.54 1.76 Ｆ 34.07 39.06 Ｏ 16.45 16.63 Cl 18.25 18.10 C4H2F4O2Cl2として 計算値 実測値 Ｃ 20.96 20.77 Ｈ 0.87 0.88 Ｆ 33.19 33.15 Ｏ 13.97 14.06 Cl 31.00 31.14 C4HF4O2Cl3として 計算値 実測値 Ｃ 18.22 18.14 Ｈ 0.38 0.42 Ｆ 28.84 28.98 Ｏ 12.14 12.27 Cl 40.42 40.19 実施例２ 実施例１と同様にして、2,3,3,3−テトラフルオロプロ
パン酸メチル544g（3.40モル）を仕込んだ。次に75ワツ
ト高圧水銀灯照射下、塩素を112cc/min（５ミリモル/mi
n）の割合で仕込み、40℃で７時間反応させた。反応終
了後蒸留により、2,3,3,3−テトラフルオロプロパン酸
モノクロロメチル292g及び2,3,3,3−テトラフルオロプ
ロパン酸ジクロロメチル21gを得た。なお、同時に未反
応の2,3,3,3−テトラフルオロプロパン酸メチル226gを
回収した。Elemental analysis (%) Calculated value as C 4 H 3 F 4 O 2 Cl Measured value C 24.68 24.45 H 1.54 1.76 F 34.07 39.06 O 16.45 16.63 Cl 18.25 18.10 C 4 H 2 F 4 O 2 Cl 2 Calculated value Measured value C 20.96 20.77 H 0.87 0.88 F 33.19 33.15 O 13.97 14.06 Cl 31.00 31.14 C 4 HF 4 O 2 Cl 3 Calculated value C 18.22 18.14 H 0.38 0.42 F 28.84 28.98 O 12.14 12.27 Cl 40.42 40.19 Example 2 Same as Example 1 Then, 544 g (3.40 mol) of methyl 2,3,3,3-tetrafluoropropanoate was charged. Next, under the irradiation of a 75-watt high-pressure mercury lamp, chlorine was added at 112 cc / min (5 mmol / mi
It was charged in the ratio of n) and reacted at 40 ° C. for 7 hours. After completion of the reaction, distillation was performed to obtain 292 g of monochloromethyl 2,3,3,3-tetrafluoropropanoate and 21 g of dichloromethyl 2,3,3,3-tetrafluoropropanoate. At the same time, 226 g of unreacted methyl 2,3,3,3-tetrafluoropropanoate was recovered.
実施例３ 温度計、コンデンサー及び撹拌機を備えた１四つ口フ
ラスコに、二酸化ケイ素36.0g（0.60モル）及び濃硫酸6
0.0g（0.61モル）を仕込み、系内を60℃に加熱して、参
考例２で得た１−モノクロロメトキシ−1,1,2,3,3,3−
ヘキサフルオロプロパン216.5g（1.0モル）を滴下し
た。滴下終了後、２時間撹拌した。反応が終了した後、
蒸留によって2,3,3,3−テトラフルオロプロパン酸モノ
クロロメチル161.4g（収率83％）を得た。Example 3 In a one-necked flask equipped with a thermometer, a condenser and a stirrer, 36.0 g (0.60 mol) of silicon dioxide and 6 parts of concentrated sulfuric acid were added.
0.0 g (0.61 mol) was charged and the system was heated to 60 ° C. to obtain 1-monochloromethoxy-1,1,2,3,3,3-obtained in Reference Example 2.
Hexafluoropropane 216.5 g (1.0 mol) was added dropwise. After completion of dropping, the mixture was stirred for 2 hours. After the reaction is complete,
By distillation, 161.4 g (yield: 83%) of monochloromethyl 2,3,3,3-tetrafluoropropanoate was obtained.
実施例４ 温度計、コンデンサー及び撹拌機を備えた１四つ口フ
ラスコに、二酸化ケイ素36.0g（0.60モル）及びフルオ
ロ硫酸30.0g（0.30モル）を仕込み、系内を55℃に加熱
して、参考例２で得た１−モノクロロメトキシ−1,1,2,
3,3,3−ヘキサフルオロプロパン216.5g（1.0モル）を滴
下した。滴下終了後、４時間撹拌した。反応が終了した
後、蒸留によって2,3,3,3−テトラフルオロプロパン酸
モノクロロメチル165.3g（収率85％）を得た。Example 4 A one-four-necked flask equipped with a thermometer, a condenser and a stirrer was charged with 36.0 g (0.60 mol) of silicon dioxide and 30.0 g (0.30 mol) of fluorosulfuric acid, and the system was heated to 55 ° C. 1-monochloromethoxy-1,1,2, obtained in Reference Example 2
216.5 g (1.0 mol) of 3,3,3-hexafluoropropane was added dropwise. After completion of dropping, the mixture was stirred for 4 hours. After the reaction was completed, 165.3 g (yield 85%) of monochloromethyl 2,3,3,3-tetrafluoropropanoate was obtained by distillation.
本発明によれば、2,3,3,3−テトラフルオロプロペンの
中間体として有用な新規含フツ素化合物を容易に提供す
ることができる。According to the present invention, a novel fluorine-containing compound useful as an intermediate for 2,3,3,3-tetrafluoropropene can be easily provided.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification number Office reference number FI technical display location // C07B 61/00 300
Claims (3)
素原子を表す。〕 で示される新規含フツ素化合物。1. A general formula CF 3 CHFCO 2 CClX 1 X 2 [wherein, X 1 and X 2 are the same or different and each represents a hydrogen atom or a chlorine atom. ] The novel fluorine-containing compound shown by these.
ルを光の照射下に塩素と接触させることを特徴とする一
般式 CF3CHFCO2CClX1X2 〔式中、X1及びX2は同一又は相異なり、水素原子又は塩
素原子を表す。〕 で示される新規含フツ素化合物の製法。2. A 2,3,3,3 general formula CF 3 CHFCO 2 CClX 1 X 2 wherein, characterized in that the tetrafluoro propanoate is contacted with chlorine under irradiation with light, X 1 and X 2 is the same or different and represents a hydrogen atom or a chlorine atom. ] The manufacturing method of the novel fluorine-containing compound shown by these.
ヘキサフルオロプロパンを酸触媒存在下で加水分解する
ことを特徴とする2,3,3,3−テトラフルオロプロパン酸
モノクロロメチルの製法。3. 1-Monorochloromethoxy-1,1,2,3,3,3-
A process for producing monochloromethyl 2,3,3,3-tetrafluoropropanoate, which comprises hydrolyzing hexafluoropropane in the presence of an acid catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62140570A JPH0749391B2 (en) | 1987-06-04 | 1987-06-04 | Fluorine-containing compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62140570A JPH0749391B2 (en) | 1987-06-04 | 1987-06-04 | Fluorine-containing compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63303950A JPS63303950A (en) | 1988-12-12 |
| JPH0749391B2 true JPH0749391B2 (en) | 1995-05-31 |
Family
ID=15271758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62140570A Expired - Fee Related JPH0749391B2 (en) | 1987-06-04 | 1987-06-04 | Fluorine-containing compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0749391B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001021573A1 (en) * | 1999-09-24 | 2001-03-29 | Daikin Industries, Ltd. | Process for terminal chlorination of fluorinated compounds |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
| US20040089839A1 (en) | 2002-10-25 | 2004-05-13 | Honeywell International, Inc. | Fluorinated alkene refrigerant compositions |
| US7524805B2 (en) | 2004-04-29 | 2009-04-28 | Honeywell International Inc. | Azeotrope-like compositions of tetrafluoropropene and hydrofluorocarbons |
| US8008244B2 (en) | 2004-04-29 | 2011-08-30 | Honeywell International Inc. | Compositions of tetrafluoropropene and hydrocarbons |
-
1987
- 1987-06-04 JP JP62140570A patent/JPH0749391B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63303950A (en) | 1988-12-12 |
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