JP2517304B2 - Method for producing bromoacetonitrile - Google Patents
Method for producing bromoacetonitrileInfo
- Publication number
- JP2517304B2 JP2517304B2 JP62204549A JP20454987A JP2517304B2 JP 2517304 B2 JP2517304 B2 JP 2517304B2 JP 62204549 A JP62204549 A JP 62204549A JP 20454987 A JP20454987 A JP 20454987A JP 2517304 B2 JP2517304 B2 JP 2517304B2
- Authority
- JP
- Japan
- Prior art keywords
- bromoacetonitrile
- producing
- reaction
- present
- bromine
- 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
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
Description
【発明の詳細な説明】 〈産業上の利用分野〉 本発明は、ブロモアセトニトリルの新しい製造方法に
関する。TECHNICAL FIELD The present invention relates to a new method for producing bromoacetonitrile.
ブロモアセトニトリルは、農薬、医薬等の有用な中間
体である。Bromoacetonitrile is a useful intermediate for agricultural chemicals, pharmaceuticals and the like.
〈従来の技術及びその問題点〉 従来、ブロモアセトニトリルの製法としては、例え
ば、下記式 に示される方法が知られている（Bulletein de la Soci
ete Chimique de Franse,〔２〕47,400）が、この方法
は原料のICH2CNの合成が困難であり、工業的製造方法と
しては向かない。<Conventional technology and its problems> Conventionally, as a method for producing bromoacetonitrile, for example, the following formula Is known (Bulletein de la Soci
ete Chimique de Franse, [2] 47, 400), the method is difficult to synthesis of ICH 2 CN raw materials not suitable as an industrial production method.
一方，ブロモアセトニトリルを製造する他の方法とし
ては、（１）ホルムアルデヒドを青酸によりシアンヒド
リンとした後、臭化水素により置換する方法、（２）酢
酸を臭素によりブロム化した後、アミド化し、次いで脱
水する方法などが考えられる。On the other hand, as another method for producing bromoacetonitrile, (1) formaldehyde is converted to cyanohydrin with hydrocyanic acid and then replaced with hydrogen bromide, and (2) acetic acid is brominated with bromine, then amidated, and then dehydrated. The method of doing it is possible.
しかしながら、これらの方法では、実質的に二工程以
上を必要とし、工業的製造方法としては充分なものとは
言えない。However, these methods require substantially two or more steps and are not sufficient as an industrial manufacturing method.
このようなことから、本発明者らは工業的・実際的に
有利にブロモアセトニトリルを製造すべく種々検討の結
果、アセトニトリルを臭素によりブロム化する方法にお
いて、反応系に三臭化リンを添加することにより、短時
間・高選択率・高収率で目的とするブロモアセトニトリ
ルが得られることを見い出し、本発明を完成するに至っ
た。From the above, the present inventors have conducted various studies to industrially and practically advantageously produce bromoacetonitrile, and as a result, in the method of brominating acetonitrile with bromine, phosphorus tribromide is added to the reaction system. As a result, they have found that the desired bromoacetonitrile can be obtained in a short time, with high selectivity and high yield, and have completed the present invention.
〈問題点を解決するための手段〉 本発明は、アセトニトリルを臭素によりブロム化し、
ブロモアセトニトリルを製造する方法において、反応系
に三臭化リンを共存させることを特徴とするブロモアセ
トニトリルの製造方法を提供するものである。<Means for Solving Problems> The present invention is a method of brominating acetonitrile with bromine,
A method for producing bromoacetonitrile, which comprises allowing phosphorus tribromide to coexist in a reaction system.
本発明の方法の反応式を示すと次の通りである。 The reaction formula of the method of the present invention is shown below.
以下に、本発明を詳細に説明する。 The present invention will be described in detail below.
本発明方法において、臭素の使用量は原料アセトニト
リルに対して0.01〜２倍モルの範囲、特に好ましくは0.
01〜１倍モルの範囲である。In the method of the present invention, the amount of bromine used is in the range of 0.01 to 2 times the molar amount of the starting material acetonitrile, particularly preferably 0.
It is in the range of 01 to 1 mol.
また、三臭化リンの使用量は原料アセトニトリルに対
して0.001〜0.1倍モルの範囲で用いられる。もちろん0.
1倍モルを超えても問題はないが原料費の増加を招くこ
とになって不経済であり、また0.001倍モル以下では、
反応の進行が極めて遅くなり、好ましくない。The amount of phosphorus tribromide used is 0.001 to 0.1 times the molar amount of the starting material acetonitrile. Of course 0.
There is no problem even if it exceeds 1 time mol, but it is uneconomical because it causes an increase in raw material cost, and if it is 0.001 times mol or less,
The reaction is extremely slow, which is not preferable.
反応温度は、40〜90℃の範囲で選ばれるが、好ましく
は60〜85℃である。The reaction temperature is selected in the range of 40 to 90 ° C, preferably 60 to 85 ° C.
本発明を実施するにあたり、通常のブロム化反応で使
用されるクロロホルム、四塩化炭素等の有機溶剤を使用
しても差支えないが、無溶剤でも何ら支障なく反応を進
めることが出来るので、工業的な面から考えれば、むし
ろ溶媒を使用しない方が好ましい。In carrying out the present invention, it is possible to use an organic solvent such as chloroform, carbon tetrachloride or the like used in a usual bromination reaction, but since the reaction can proceed without any trouble even without a solvent, industrially. Therefore, it is preferable not to use a solvent.
反応の進行は機器分析、たとえばガスクロマトグラフ
ィーにより追跡される。The progress of the reaction is followed by instrumental analysis, eg gas chromatography.
反応液からのブロモアセトニトリルの取り出しは、た
とえば水洗の後、蒸留することにより行なわれる。Removal of bromoacetonitrile from the reaction solution is carried out, for example, by washing with water and then distilling.
〈発明の効果〉 本発明によれば、工業的有利にブロモアセトニトリル
を製造することができる。<Effect of the Invention> According to the present invention, bromoacetonitrile can be industrially advantageously produced.
このブロモアセトニトリルは、ｔ−ブチルブロマイ
ド、さらにはα−メチルスチレンと反応させることによ
り、農薬として有用な２−ブロモ−3,3−ジメチル−Ｎ
−（α，α−ジメチルベンジル）ブチルアミドに変換さ
れることが、本発明者らによって見出されており、本発
明はこの目的のために、極めて有効なプロセスとなる。This bromoacetonitrile is reacted with t-butyl bromide and α-methylstyrene to give 2-bromo-3,3-dimethyl-N useful as a pesticide.
It has been found by the present inventors to be converted to-(α, α-dimethylbenzyl) butyramide, which makes this a very effective process for this purpose.
〈実施例〉 以下、実施例により、本発明を説明する。<Examples> Hereinafter, the present invention will be described with reference to Examples.
実施例１ フラスコにアセトニトリル205.5部、三臭化リン10.8
部を仕込んだ後、撹拌下に80±３℃に維持しながら臭素
32.0部を１時間を要して滴下した。滴下終了後、同温度
で１時間保持した。反応終了後、反応液を水洗した後、
精留することにより、ブロモアセトニトリル22.0部（含
量99.3％）を得た。収率91.0％対仕込臭素、選択率98.9
％。Example 1 205.5 parts of acetonitrile and 10.8 phosphorus tribromide in a flask
Parts, then brominated while maintaining at 80 ± 3 ℃ under stirring
32.0 parts was added dropwise over 1 hour. After the dropping was completed, the temperature was maintained at the same temperature for 1 hour. After the reaction, after washing the reaction solution with water,
By rectifying, 22.0 parts (content 99.3%) of bromoacetonitrile was obtained. Yield 91.0% vs. charged bromine, selectivity 98.9
%.
実施例２ フラスコにアセトニトリル205.5部、三臭化リン16.2
部を仕込んだ後、撹拌下に75±３℃に維持しながら臭素
160部を２時間を要して滴下した。滴下終了後、同温度
で３時間保持した。反応終了後、反応液を水洗した後、
精留することにより、ブロモアセトニトリル103部（含
量99.0％）を得た。収率85.0％対仕込臭素、選択率95.2
％。Example 2 205.5 parts of acetonitrile, 16.2 phosphorus tribromide in a flask
Part, and then bromine while stirring and maintaining at 75 ± 3 ℃
160 parts was added dropwise over 2 hours. After the dropping was completed, the temperature was maintained for 3 hours. After the reaction, after washing the reaction solution with water,
Fractionation gave 103 parts of bromoacetonitrile (content 99.0%). Yield 85.0% vs. charged bromine, selectivity 95.2
%.
Claims (1)
ブロモアセトニトリルを製造する方法において、反応系
に三臭化リンを共存させることを特徴とするブロモアセ
トニトリルの製造方法。1. Brominated acetonitrile with bromine,
A method for producing bromoacetonitrile, which comprises allowing phosphorus tribromide to coexist in a reaction system.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62204549A JP2517304B2 (en) | 1987-08-17 | 1987-08-17 | Method for producing bromoacetonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62204549A JP2517304B2 (en) | 1987-08-17 | 1987-08-17 | Method for producing bromoacetonitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6447751A JPS6447751A (en) | 1989-02-22 |
| JP2517304B2 true JP2517304B2 (en) | 1996-07-24 |
Family
ID=16492345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62204549A Expired - Fee Related JP2517304B2 (en) | 1987-08-17 | 1987-08-17 | Method for producing bromoacetonitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2517304B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114507157B (en) * | 2020-11-17 | 2023-03-24 | 沧州维智达美制药有限公司 | Method for preparing bromoacetonitrile by using chloroacetonitrile |
| CN113582874B (en) * | 2021-09-10 | 2023-09-22 | 宁夏常晟药业有限公司 | Synthesis method of bromoacetonitrile |
| CN114591199B (en) * | 2022-03-17 | 2024-03-12 | 诚弘制药(威海)有限责任公司 | Preparation method of bromoacetonitrile |
-
1987
- 1987-08-17 JP JP62204549A patent/JP2517304B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6447751A (en) | 1989-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |