JP3164284B2 - Method for producing 2-chloro-4-trifluoromethylbenzal chloride - Google Patents
Method for producing 2-chloro-4-trifluoromethylbenzal chlorideInfo
- Publication number
- JP3164284B2 JP3164284B2 JP07179196A JP7179196A JP3164284B2 JP 3164284 B2 JP3164284 B2 JP 3164284B2 JP 07179196 A JP07179196 A JP 07179196A JP 7179196 A JP7179196 A JP 7179196A JP 3164284 B2 JP3164284 B2 JP 3164284B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chloro
- trifluoromethylbenzal
- chloride
- producing
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、医薬品、農薬、各
種機能性材料などの製造中間体として有用な化合物であ
る式［Ｉ］TECHNICAL FIELD The present invention relates to a compound of the formula [I] which is a compound useful as an intermediate for producing pharmaceuticals, agricultural chemicals, various functional materials and the like.
【０００２】[0002]
【化５】 Embedded image
【０００３】で示される２−クロロ−４−トリフルオロ
メチルベンザルクロライドの製造方法に関するものであ
る。The present invention relates to a method for producing 2-chloro-4-trifluoromethylbenzal chloride represented by the formula:
【０００４】[0004]
【発明が解決しようとする課題】従来、２−クロロ−４
−トリフルオロメチルベンザルクロライドを製造する方
法としては、以下に示されるように２−クロロキシレン
を出発原料とし、光塩素化して得られる２−クロロ−４
−トリクロロメチルベンザルクロライドを蒸留により分
離し、これをフッ素化し、さらに蒸留することにより製
造する方法が知られている［ＵＳＰ４，３６７，３４
８］。SUMMARY OF THE INVENTION Conventionally, 2-chloro-4
As a method for producing -trifluoromethylbenzal chloride, 2-chloro-4 obtained by photochlorinating 2-chloroxylene as a starting material as shown below is used.
A method is known in which trichloromethylbenzal chloride is separated by distillation, fluorinated, and further distilled to produce [USP 4,367,34].
8].
【０００５】[0005]
【化６】 Embedded image
【０００６】しかしながら、上記の製造方法において
は、収率や選択率が低く、また、工程数が多いため、工
業的な製造方法ではない。However, the above-mentioned production method is not an industrial production method because the yield and selectivity are low and the number of steps is large.
【０００７】[0007]
【課題を解決するための手段】本発明者は、かかる問題
点に鑑み、２−クロロ−４−トリフルオロメチルベンザ
ルクロライドを工業的に容易に、かつ、効率よく製造す
ることができる方法について、鋭意、検討を行った結
果、４−トリフルオロメチルベンザルクロライドを塩素
化することにより、２−クロロ−４−トリフルオロメチ
ルベンザルクロライドを容易に製造することができるこ
とを見出し、本発明に到達した。SUMMARY OF THE INVENTION In view of the above problems, the present inventor has proposed a method for industrially easily and efficiently producing 2-chloro-4-trifluoromethylbenzal chloride. As a result of intensive studies, it was found that 2-chloro-4-trifluoromethylbenzal chloride can be easily produced by chlorinating 4-trifluoromethylbenzal chloride. Reached.
【０００８】すなわち、本発明の第一は、式［ＩＩ］That is, the first aspect of the present invention is to provide a compound of the formula [II]
【０００９】[0009]
【化７】 Embedded image
【００１０】で示される４−トリフルオロメチルベンザ
ルクロライドをルイス酸触媒の存在下、塩素と反応させ
ることを特徴とする式［Ｉ］Wherein 4-trifluoromethylbenzal chloride represented by the formula (I) is reacted with chlorine in the presence of a Lewis acid catalyst.
【００１１】[0011]
【化８】 Embedded image
【００１２】で示される２−クロロ−４−トリフルオロ
メチルベンザルクロライドの製造方法である。また、本
発明の第二は、式［ＩＩ］A method for producing 2-chloro-4-trifluoromethylbenzal chloride represented by the formula: In the second aspect of the present invention, the compound represented by the formula [II]
【００１３】[0013]
【化９】 Embedded image
【００１４】で示される４−トリフルオロメチルベンザ
ルクロライドをルイス酸触媒およびヨウ素の存在下、塩
素と反応させることを特徴とする式［Ｉ］Reacting 4-trifluoromethylbenzal chloride represented by the formula (I) with chlorine in the presence of a Lewis acid catalyst and iodine.
【００１５】[0015]
【化１０】 Embedded image
【００１６】で示される２−クロロ−４−トリフルオロ
メチルベンザルクロライドの製造方法である。以下、本
発明を詳細に説明する。A method for producing 2-chloro-4-trifluoromethylbenzal chloride represented by the formula: Hereinafter, the present invention will be described in detail.
【００１７】本発明における出発原料である式［ＩＩ］
で示される４−トリフルオロメチルベンザルクロライド
は、ｐ−キシレンを原料とし、塩素化して４−トリクロ
ロメチルベンザルクロライドを得、これをフッ素化する
ことにより、容易に製造することができる。In the present invention, the starting material represented by the formula [II]
Can be easily produced by chlorinating p-xylene as a raw material to obtain 4-trichloromethylbenzal chloride, which is fluorinated.
【００１８】本発明においては、上記の式［ＩＩ］で示
される４−トリフルオロメチルベンザルクロライドをル
イス酸触媒の存在下、塩素と反応させることにより、目
的の式［Ｉ］で示される２−クロロ−４−トリフルオロ
メチルベンザルクロライドを非常に容易に製造すること
ができる。In the present invention, 4-trifluoromethylbenzal chloride represented by the above formula [II] is reacted with chlorine in the presence of a Lewis acid catalyst to obtain the desired compound represented by the formula [I]. -Chloro-4-trifluoromethylbenzal chloride can be produced very easily.
【００１９】本発明におけるルイス酸触媒は、通常使用
されているものを使用すればよく、具体的には、例え
ば、塩化第二鉄などが挙げられる。本発明におけるルイ
ス酸触媒の使用量は、式［ＩＩ］で示される４−トリフ
ルオロメチルベンザルクロライド１当量に対して、通
常、０．００１当量〜０．２当量、好ましくは０．００
５当量〜０．１当量、さらに好ましくは０．０１当量〜
０．０５当量となるように使用するのがよい。この範囲
より少ない場合には、反応が充分に進行せず、収率低下
の原因となり、経済的に不利となる、あるいは、反応速
度が低下して反応終了までに長時間を要するなどの問題
を生ずる場合があり、好ましくない。また、この範囲よ
り多く使用しても、目的とする式［Ｉ］で示される２−
クロロ−４−トリフルオロメチルベンザルクロライドの
収率、反応速度などにほとんど変化はなく、経済的に不
利となるだけであり、好ましくない。As the Lewis acid catalyst used in the present invention, a commonly used Lewis acid catalyst may be used, and specific examples include ferric chloride. The amount of the Lewis acid catalyst used in the present invention is usually 0.001 equivalent to 0.2 equivalent, preferably 0.00 equivalent, per 1 equivalent of 4-trifluoromethylbenzal chloride represented by the formula [II].
5 equivalents to 0.1 equivalents, more preferably 0.01 equivalents to
It is good to use so that it may become 0.05 equivalent. If the amount is less than the above range, the reaction does not proceed sufficiently and causes a decrease in yield, which is economically disadvantageous, or there is a problem that the reaction speed decreases and it takes a long time to complete the reaction. May occur, which is not preferred. Further, even if the amount is larger than this range, the desired compound represented by the formula [I] 2-
There is almost no change in the yield, reaction rate, etc. of chloro-4-trifluoromethylbenzal chloride, which is economically disadvantageous and is not preferred.
【００２０】本発明においては、原料である式［ＩＩ］
で示される４−トリフルオロメチルベンザルクロライド
およびルイス酸触媒を反応器に仕込んだ後、塩素ガスを
導入することにより塩素化反応を行う。塩素の導入方法
は、特に限定はなく、通常行われている方法を採用すれ
ばよく、例えば、塩素ガスを反応溶液中に連続的に吹き
込む方法などがある。In the present invention, the starting material represented by the formula [II]
After charging 4-trifluoromethylbenzal chloride and a Lewis acid catalyst represented by the formula (1) into a reactor, a chlorination reaction is carried out by introducing chlorine gas. The method for introducing chlorine is not particularly limited, and a method generally used may be employed. For example, there is a method of continuously blowing chlorine gas into the reaction solution.
【００２１】また、本発明における反応温度は、通常、
３０℃〜１００℃、好ましくは４０℃〜９０℃、さらに
好ましくは５０℃〜８０℃とするのがよい。この範囲よ
り低い温度の場合には、反応が充分に進行せず、収率低
下の原因となり、経済的に不利となる、あるいは、反応
速度が低下して反応終了までに長時間を要するなどの問
題を生ずる場合があり、好ましくない。また、この範囲
より高い温度の場合には、反応中に分解などが起こる場
合があり、収率低下の原因となり、経済的に不利とな
り、また、分解生成物などの除去のために後処理工程に
負荷がかかるため、好ましくない。The reaction temperature in the present invention is usually
The temperature is 30 ° C to 100 ° C, preferably 40 ° C to 90 ° C, and more preferably 50 ° C to 80 ° C. If the temperature is lower than this range, the reaction does not proceed sufficiently and causes a decrease in yield, which is economically disadvantageous, or the reaction speed decreases and it takes a long time to complete the reaction. This may cause problems and is not preferred. If the temperature is higher than this range, decomposition or the like may occur during the reaction, which causes a decrease in yield, which is economically disadvantageous, and a post-treatment step for removing decomposition products and the like. This is not preferable because the load is imposed on it.
【００２２】本発明においては、上記のようにして目的
とする式［Ｉ］で示される２−クロロ−４−トリフルオ
ロメチルベンザルクロライドを製造することができる
が、さらにヨウ素を添加することにより反応速度が上が
り、より効率よく反応を行うことができる。In the present invention, the desired 2-chloro-4-trifluoromethylbenzal chloride represented by the formula [I] can be produced as described above, but by further adding iodine. The reaction rate increases, and the reaction can be performed more efficiently.
【００２３】ヨウ素の使用量は、特に限定はなく、求め
る反応速度に応じて適宜調節すればよいが、通常、原料
である式［ＩＩ］で示される４−トリフルオロメチルベ
ンザルクロライド１当量に対して０．０００１当量〜
０．０２当量、好ましくは０．０００５当量〜０．０１
当量、さらに好ましくは０．００１当量〜０．００５当
量使用するのがよい。この範囲より少ない場合には、反
応を促進し、反応をより効率的に行うという目的が充分
に達成されない場合があるため、好ましくない。また、
この範囲より多く使用しても、反応速度、収率などにほ
とんど変化はなく、経済的に不利となるだけであり、好
ましくない。The amount of iodine used is not particularly limited and may be appropriately adjusted according to the desired reaction rate. Usually, the amount of iodine is equivalent to 1 equivalent of 4-trifluoromethylbenzal chloride represented by the formula [II] as a raw material. 0.0001 equivalent to
0.02 equivalents, preferably 0.0005 equivalents to 0.01
It is better to use an equivalent, more preferably 0.001 to 0.005 equivalent. If the amount is less than this range, the purpose of accelerating the reaction and performing the reaction more efficiently may not be sufficiently achieved, which is not preferable. Also,
Use of more than this range hardly changes the reaction rate, yield, etc., and is only economically disadvantageous, which is not preferable.
【００２４】本発明においては、反応終了後、通常の後
処理を行えばよい。本発明の製造方法において製造され
た粗生成物は、単蒸留により容易に精製することがで
き、目的とする式［Ｉ］で示される２−クロロ−４−ト
リフルオロメチルベンザルクロライドを高純度で得るこ
とができる。In the present invention, after the reaction is completed, ordinary post-treatment may be performed. The crude product produced by the production method of the present invention can be easily purified by simple distillation, and the desired 2-chloro-4-trifluoromethylbenzal chloride represented by the formula [I] can be purified to a high purity. Can be obtained at
【００２５】本発明においては、以上のようにして、医
薬品、農薬、各種機能材料などの製造中間体として有用
な化合物である式［Ｉ］で示される２−クロロ−４−ト
リフルオロメチルベンザルクロライドを容易に、かつ、
効率よく製造することができる。In the present invention, as described above, 2-chloro-4-trifluoromethylbenzal represented by the formula [I], which is a compound useful as an intermediate for producing pharmaceuticals, agricultural chemicals, various functional materials, etc. Easy chloride and
It can be manufactured efficiently.
【００２６】[0026]
【発明の実施の形態】以下、実施例により、本発明の実
施の形態を具体的に説明する。DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of the present invention will be specifically described below with reference to examples.
【００２７】[0027]
【実施例】実施例１ ｐ−トリフルオロメチルベンザルクロライド２２９．０
ｇ、塩化第二鉄１１．５ｇ、ヨウ素１．２ｇを１Ｌガラ
ス製反応器に仕込み、６０℃まで昇温した。これに塩素
ガスを０．３ｍｏｌ／ｈで吹き込み８時間反応させる。
反応後純度は、８０％（Ｇ．Ｃ．ａｒｅａ％）であり、
これを単蒸留することにより２−クロロ−４−トリフル
オロメチルベンザルクロライド２０２．５ｇ（純度９９
％）を得た。EXAMPLES Example 1 229.0 p-trifluoromethylbenzal chloride
g, ferric chloride 11.5 g, and iodine 1.2 g were charged into a 1 L glass reactor, and the temperature was raised to 60 ° C. Chlorine gas is blown into the mixture at a rate of 0.3 mol / h to react for 8 hours.
The purity after the reaction is 80% (GC area%),
This was subjected to simple distillation to give 202.5 g of 2-chloro-4-trifluoromethylbenzal chloride (purity 99).
%).
【００２８】[0028]
【発明の効果】医薬品、農薬、各種機能材料などの製造
中間体として有用な化合物である２−クロロ−４−トリ
フルオロメチルベンザルクロライドを容易に、かつ、効
率よく製造することができる。According to the present invention, 2-chloro-4-trifluoromethylbenzal chloride, which is a compound useful as an intermediate for producing pharmaceuticals, agricultural chemicals and various functional materials, can be produced easily and efficiently.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C07C 17/12 C07C 25/13 ＣＡ（ＳＴＮ) ＣＡＯＬＤ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 7 , DB name) C07C 17/12 C07C 25/13 CA (STN) CAOLD (STN) REGISTRY (STN)
Claims (2)
をルイス酸触媒の存在下、塩素と反応させることを特徴
とする式［Ｉ］ 【化２】 で示される２−クロロ−４−トリフルオロメチルベンザ
ルクロライドの製造方法。1. A compound of the formula [II] Wherein 4-trifluoromethylbenzal chloride represented by the formula is reacted with chlorine in the presence of a Lewis acid catalyst. A method for producing 2-chloro-4-trifluoromethylbenzal chloride represented by the formula:
をルイス酸触媒およびヨウ素の存在下、塩素と反応させ
ることを特徴とする式［Ｉ］ 【化４】 で示される２−クロロ−４−トリフルオロメチルベンザ
ルクロライドの製造方法。2. A compound of the formula [II] Wherein 4-trifluoromethylbenzal chloride represented by the formula (I) is reacted with chlorine in the presence of a Lewis acid catalyst and iodine. A method for producing 2-chloro-4-trifluoromethylbenzal chloride represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07179196A JP3164284B2 (en) | 1996-03-27 | 1996-03-27 | Method for producing 2-chloro-4-trifluoromethylbenzal chloride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP07179196A JP3164284B2 (en) | 1996-03-27 | 1996-03-27 | Method for producing 2-chloro-4-trifluoromethylbenzal chloride |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH09255600A JPH09255600A (en) | 1997-09-30 |
| JP3164284B2 true JP3164284B2 (en) | 2001-05-08 |
Family
ID=13470759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP07179196A Expired - Fee Related JP3164284B2 (en) | 1996-03-27 | 1996-03-27 | Method for producing 2-chloro-4-trifluoromethylbenzal chloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3164284B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR200496846Y1 (en) * | 2021-03-07 | 2023-05-10 | 김수현 | Mat of car camping |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114702380B (en) * | 2022-04-07 | 2024-03-19 | 河南特格纳特科技有限公司 | Method for co-producing p-chlorobenzoyl chloride and hexanoyl chloride and acyl chloride product thereof |
-
1996
- 1996-03-27 JP JP07179196A patent/JP3164284B2/en not_active Expired - Fee Related
Cited By (1)
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|---|---|---|---|---|
| KR200496846Y1 (en) * | 2021-03-07 | 2023-05-10 | 김수현 | Mat of car camping |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09255600A (en) | 1997-09-30 |
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|---|---|---|---|
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