JPS6036453A - Preparation of pentafluorobenzonitrile - Google Patents
Preparation of pentafluorobenzonitrileInfo
- Publication number
- JPS6036453A JPS6036453A JP14520583A JP14520583A JPS6036453A JP S6036453 A JPS6036453 A JP S6036453A JP 14520583 A JP14520583 A JP 14520583A JP 14520583 A JP14520583 A JP 14520583A JP S6036453 A JPS6036453 A JP S6036453A
- Authority
- JP
- Japan
- Prior art keywords
- pentachlorobenzonitrile
- reaction
- potassium fluoride
- raw material
- pentafluorobenzonitrile
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、ペンタクロロベンゾニトリルとフン化カリウ
ムとを無溶媒、加圧下で反応させて、各種農薬、医薬或
いは染料などの中ｔｉｌｌ原料として有用なペンタフル
オロベンゾニトリルを製造する方法に関する。Detailed Description of the Invention The present invention produces pentafluorobenzonitrile, which is useful as a till raw material for various agricultural chemicals, pharmaceuticals, dyes, etc., by reacting pentachlorobenzonitrile and potassium fluoride without a solvent and under pressure. Relating to a method of manufacturing.
従来、ペンタクロロベンゾニトリル（以下ＰＣＢＮと略
す）の総ての塩素原子をフッ素原子に置換したペンタフ
ルオロベンゾニトリル（以下ＰＦＢＮと略す）を製造す
る方法としては、例えばノヤーナルオブサケミ力ルソサ
エテイ（オーカ゛ニックケミストリー）１３４ Ｊ〜１
３．１２頁、（１９７１）［Ｊ、Ｃｈｅ＋ＩＩ、Ｓｏｃ
、（Ｃ）Ｐ１３４１−１３４２、（１９７１）］に記載
された方法が知られている。Conventionally, as a method for producing pentafluorobenzonitrile (hereinafter abbreviated as PFBN) in which all chlorine atoms of pentachlorobenzonitrile (hereinafter abbreviated as PCBN) are replaced with fluorine atoms, for example, Noyanal Observatory Society (hereinafter abbreviated as PCBN) is used. organic chemistry) 134 J~1
3.12 pages, (1971) [J, Che+II, Soc.
, (C) P1341-1342, (1971)] is known.
しかしながら、上記方法では、大過剰のフン化カリウム
と、反応に長時間を要するために経済的に不利であり、
より工業的に有利な方法の出現がめられている。However, the above method is economically disadvantageous because it requires a large excess of potassium fluoride and a long reaction time.
A more industrially advantageous method is expected to emerge.
本発明者達は、この反応が固相反応である為に、オート
クレーブ中での攪拌が困難であり、反応性か悪いことに
注目し、溶媒、例えばＮ−メチル−２−ピロリドン、ス
ルホラン、ベンゾニトリル、中学≠＃などを用いる方法
や、更には触媒を添加する方法を試みたが、いずれの方
法も良好な結果は得られなかった。一方、ＰＣＢＮを、
特定条件下７ノ化カリウムと反応させた場合、２ 、４
、６− トリフルオａ−３゜５−ツクａａベンゾニト
リルが効率良く得られることに注目し、このものを経由
する二段或いは多段法を試みた。しかしながら、この方
法も良好な結果は得られなかった。The present inventors noted that since this reaction is a solid phase reaction, stirring in an autoclave is difficult and the reactivity is poor, and solvents such as N-methyl-2-pyrrolidone, sulfolane, benzene, etc. Methods using nitrile, ##, etc., and methods of adding a catalyst were also tried, but no good results were obtained with any of the methods. On the other hand, PCBN,
When reacted with potassium heptaconide under specific conditions, 2,4
, 6-trifluoro-a-3°5-tsuk-aa-benzonitrile was noted to be efficiently obtained, and a two-stage or multi-stage method using this product was attempted. However, this method also did not give good results.
本発明者達は更に検討を重ね、１１；Ｊ記文献に何の示
唆もない７ノ化カリウムの量を減量し、反応を試みた結
果、意外にも特定の温度範囲で、短時間にＰｌ・”ＢＮ
が良好な収率で待−られることの知見を得、本発明を完
成するに至った。The inventors of the present invention conducted further studies, and as a result of reducing the amount of potassium heptanotide, which is not suggested in the literature 11;・”BN
The present invention has been completed based on the knowledge that this can be achieved in good yield.
すなわち本発明は、ペンタクロロベンゾニトリルとフン
化カリウムとを反応させて、ペンタフルオロベンゾニト
リルを製造する方法において、前記ペンタクロロベンゾ
ニトリル１モルに対してフッ化カリウムを５〜１０モル
使用し、無溶媒で、加圧下、３３ ｆ） −、’（７ｔ
） ’Ｃの温度で反応さぜることを特徴とするペンタフ
ルオロベンゾニ）・リルの製造方法である。That is, the present invention provides a method for producing pentafluorobenzonitrile by reacting pentachlorobenzonitrile and potassium fluoride, using 5 to 10 moles of potassium fluoride per mole of the pentachlorobenzonitrile, Without solvent and under pressure, 33 f) -,'(7t
This is a method for producing pentafluorobenzoni), which is characterized in that the reaction is stirred at a temperature of 0.25C.
本発明で用いる原料物質のＴ’Ｃ１３Ｎは、ベンゾニト
リルを塩素化することによって容易に得ることができる
。The raw material T'C13N used in the present invention can be easily obtained by chlorinating benzonitrile.
本発明方法の実施に当っては、オー）・クレーブなどの
密閉容器中に、予め混合したＩ’ ＣＩ３ Ｎとフン化
カリウムとを投入し、加熱、攪拌することにＪ、って行
なわれる。In carrying out the method of the present invention, premixed I'CI3N and potassium fluoride are placed in a closed container such as an autoclave, and the mixture is heated and stirred.
ここで５１１いられるフン化カリウノ、は、通常の市販
品或いは極微粒物などいずれのものでも用いることがで
きるか、極微粒物の力か望ましい。その使用Ｙ１、は、
ＰＣＢＮＩモルｔこ月して５〜１０モル、望ましくは５
．５〜８モルである。The potassium fluoride used in 511 here can be either a commercially available product or an ultrafine powder, or preferably an ultrafine powder. Its use Y1 is
5 to 10 mol of PCBNI per month, preferably 5
．． It is 5 to 8 moles.
フッ化カリウムの使用量が前記範囲より少な過ぎると反
応か進み難くなり、また多過ぎても攪拌か困難となって
反応系内が不均一となり留止しくない。反応温度は３３
（１−３７０’Ｃ１望ましくは３４０〜３６ ’（，
１”Ｃである。この反応は３〜１０時間、望ましくは３
〜７時間で完結する。密閉容器中の圧力は、密封加熱に
よる自然加圧でよく、その場合圧力は太孔３ Ｋ ８／
ｃｍ” −２５ｋ）；／ Ｃ１ｌ＋”程度で・ある。If the amount of potassium fluoride used is too little than the above range, the reaction will be difficult to proceed, and if it is too much, stirring will be difficult and the inside of the reaction system will be non-uniform, making it difficult for the reaction to proceed. The reaction temperature is 33
(1-370'C1 preferably 340-36'(,
1"C. This reaction is carried out for 3 to 10 hours, preferably 3
Completes in ~7 hours. The pressure in the sealed container may be natural pressure due to sealed heating, in which case the pressure is 3K 8/
cm"-25k);/C1l+".
尚、不活性電泳などにより活閉容器内の空気を置換した
り、或いは前記圧力範囲以上に加圧しても良く、この場
合酸化或いは重合等を防止することもできる。Incidentally, the air in the active closed container may be replaced by inert electrophoresis or the like, or the pressure may be increased above the above pressure range, and in this case, oxidation, polymerization, etc. can be prevented.
この様にして（’Ｕられな反応生成物は、通常の分離、
精製手段を施さずして目的物であるＰ Ｆ Ｂ Ｎを高
純度、高収率で得ることがでとるか、より高純度とする
ため、通常の分離、精製手段を施してもよい。尚、未反
応原料や未反応生成物か反応生成物中に存在する場合に
は、例えば蒸留なとの簡単な分前「４段を施して未反胞
、物を回収し、ｆｌ＃ Ｊｕｌ使用することができるの
で、経済的である。In this way (unresolved reaction products are removed by conventional separation,
The target product P F B N can be obtained with high purity and high yield without using any purification means, or ordinary separation and purification methods may be used to obtain higher purity. In addition, if unreacted raw materials or unreacted products are present in the reaction product, use a simple process such as distillation to collect the unreacted materials and use fl#Jul. It is economical because it can be
次に本発明の実施例を記載する。Next, examples of the present invention will be described.
実施例］
圧力計、攪拌磯及び温度計を備えた１Ｑのオートクレー
ブ（ＳＵＳ製）に、予め充分混合したペンタフルオロベ
ンゾニトリル１５０ｇと乾燥したフン化カリウム２２１
．４８との（１１合物を投入した。次いで、乾燥窒素ガ
スでオートクレーブ中の空気を置換して、オートクレー
ブを密閉し、攪拌下栓々に昇温しで内温か３５０’Ｃに
なった時点から５時間反応させた。尚、この開の最大圧
力は２１ｋＨ／ｃｍ”であった。反応終了後、冷却降温
し、２００°Ｃ近辺より予めオートクレーブに（＝１設
した蒸留回収装置を用い生成物を採集し、り５．ＧＢの
油状物をイｕた。この油状物をガスクロマトグラフィー
で分析した結果、ペンタフルオロベンゾニトリルの含有
率は、）ｉ８．５％であった。（収（シ８０．５％）実
施例２〜３
次表の反応条１′１に従って、１１１ｊ記天７４％］の
場合にイ（（シて反応させ、次表の結果をイ；）た。Example] 150 g of pentafluorobenzonitrile thoroughly mixed in advance and 221 g of dried potassium fluoride were placed in a 1Q autoclave (made of SUS) equipped with a pressure gauge, a stirrer, and a thermometer.
．． Then, the air in the autoclave was replaced with dry nitrogen gas, the autoclave was sealed, and the temperature was raised using a stopper while stirring until the internal temperature reached 350'C. The reaction was allowed to proceed for 5 hours. The maximum pressure at this point was 21 kHz/cm. 5.GB of oil was collected.This oil was analyzed by gas chromatography, and the content of pentafluorobenzonitrile was 8.5%. 80.5%) Examples 2 to 3 According to reaction procedure 1'1 in the following table, the reaction was carried out in the case of 111j (74%), and the results in the following table were obtained.
Claims (1)
リ・ンムとを反応させて、ペンタフルオロベンゾニトリ
ルを製造する方法において、前記ペンタクロロベンゾニ
） ｌ）ル１モルに月して７フ化カリウムを５〜１０モ
ル使用し、無溶媒で、加圧ド、３３０〜３７０ ”ｃの
温度で反応させることを特徴とするペンタフルオロベン
ゾニトリルの製造方法。 ２、 フン化カリウムをペンタクロロベンツ゛ニトリル
１モルに月して、５．５〜８モル使用し、３４．０〜３
６１） ”Ｃの温度で反応させることを特徴とする４Ｑ
Ｊ、請求の範囲第１項に記載の製造方法。[Claims] 1. A method for producing pentafluorobenzonitrile by reacting pentafluorobenzonitrile with potassium 77ide, in which 1 mole of the pentachlorobenzonitrile is 2. Potassium fluoride is used per mole of pentachlorobenzenitrile, 5.5 to 8 moles are used, and 34.0 to 3
61) “4Q characterized by reaction at a temperature of C”
J. The manufacturing method according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14520583A JPS6036453A (en) | 1983-08-09 | 1983-08-09 | Preparation of pentafluorobenzonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14520583A JPS6036453A (en) | 1983-08-09 | 1983-08-09 | Preparation of pentafluorobenzonitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6036453A true JPS6036453A (en) | 1985-02-25 |
Family
ID=15379828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14520583A Pending JPS6036453A (en) | 1983-08-09 | 1983-08-09 | Preparation of pentafluorobenzonitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6036453A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200548A (en) * | 1984-06-04 | 1993-04-06 | Bayer Aktiengesellschaft | 2,4,5-Trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5530158A (en) * | 1984-06-04 | 1996-06-25 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
-
1983
- 1983-08-09 JP JP14520583A patent/JPS6036453A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200548A (en) * | 1984-06-04 | 1993-04-06 | Bayer Aktiengesellschaft | 2,4,5-Trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5362909A (en) * | 1984-06-04 | 1994-11-08 | Bayer Aktiengesellschaft | Process for the preparation of 3-chloro-2,4,5-trifluorobenzoyl chloride, 2,4,5-trifuluorobenzoyl fluoride, and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5530158A (en) * | 1984-06-04 | 1996-06-25 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno- and 2,3,4,5-tetrahalogenobenzene derivatives |
| US5565614A (en) * | 1984-06-04 | 1996-10-15 | Bayer Aktiengesellschaft | 2,4,5-trihalogeno-and 2,3,4,5-tetrahalogenobenzene derivatives |
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