JPH06100504A - Production of di-para tolylamine - Google Patents
Production of di-para tolylamineInfo
- Publication number
- JPH06100504A JPH06100504A JP27680592A JP27680592A JPH06100504A JP H06100504 A JPH06100504 A JP H06100504A JP 27680592 A JP27680592 A JP 27680592A JP 27680592 A JP27680592 A JP 27680592A JP H06100504 A JPH06100504 A JP H06100504A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- tolylamine
- parts
- toluidine
- 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.)
- Pending
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はジ−ｐ−トリルアミンの
製造方法に関する。FIELD OF THE INVENTION The present invention relates to a method for producing di-p-tolylamine.
【０００２】[0002]
【従来の技術】ジ−ｐ−トリルアミンの製造方法として
はｐ−トルイジンまたはアセチルトルイジンとｐ−ヨ−
ドトルエンの反応による合成が知られている。2. Description of the Prior Art As a method for producing di-p-tolylamine, p-toluidine or acetyltoluidine and p-toluidine are used.
The synthesis by the reaction of dotoluene is known.
【０００３】また、英国特許第６４４，９３８号に類似
化合物のジフェニルアミンの合成法が開示されており、
同様の方法でジトリルアミンも製造可能であることの記
載がある。この方法はアニリン１重量部に対し０．０３
重量部の塩化アルミニウムを加え、３００℃以上、１０
気圧という厳しい反応条件で実施されている。Further, British Patent 644,938 discloses a method for synthesizing a similar compound, diphenylamine,
It is described that ditolylamine can be produced by the same method. This method is 0.03 for 1 part by weight of aniline.
Add 300 parts by weight of aluminum chloride, 300 ° C or higher, 10
It is carried out under severe reaction conditions of atmospheric pressure.
【０００４】また、先に本発明者らが提案した方法とし
て、ｐ−トルイジン１重量部に対し無水塩化アルミニウ
ム０．２重量部以上または無水塩化アルミニウム０．２
重量部以上及び塩化アンモニウム０．１重量部以上を加
え、２００〜２５０℃にて反応を行わせるジ−ｐ−トリ
ルアミンの製造方法がある。As a method previously proposed by the present inventors, 0.2 part by weight or more of anhydrous aluminum chloride or 0.2 part by weight of anhydrous aluminum chloride is added to 1 part by weight of p-toluidine.
There is a method for producing di-p-tolylamine by adding at least 1 part by weight and at least 0.1 part by weight of ammonium chloride and carrying out the reaction at 200 to 250 ° C.
【０００５】[0005]
【発明が解決しようとする課題】本発明の目的はジ−ｐ
−トリルアミンの新規な製造方法を提供すること、ジ−
ｐ−トリルアミンの効率的、かつ、緩い反応条件で可能
な製造方法を提供することである。DISCLOSURE OF THE INVENTION The object of the present invention is zip
-Providing a novel method for producing tolylamine, di-
An object of the present invention is to provide an efficient production method of p-tolylamine, which is possible under mild reaction conditions.
【０００６】[0006]
【課題を解決するための手段】本発明はｐ−トルイジン
１重量部に対し無水塩化アルミニウム０．２重量部以上
及び溶媒を加え、１６０℃以上にて反応を行わせること
を特徴とするジ−ｐ−トリルアミンの製造方法から構成
される。The present invention is characterized by adding 0.2 parts by weight or more of anhydrous aluminum chloride and a solvent to 1 part by weight of p-toluidine, and carrying out the reaction at 160 ° C. or more. It is composed of a method for producing p-tolylamine.
【０００７】また、本発明はｐ−トルイジン１重量部に
対し無水塩化アルミニウム０．２重量部以上及び塩化ア
ンモニウム０．１重量部以上及び溶媒を加え、１６０℃
以上にて反応を行わせることを特徴とするジ−ｐ−トリ
ルアミンの製造方法から構成される。Further, in the present invention, 1 part by weight of p-toluidine, 0.2 parts by weight or more of anhydrous aluminum chloride, 0.1 parts by weight or more of ammonium chloride and a solvent are added, and the mixture is heated to 160 ° C.
It comprises a method for producing di-p-tolylamine, which is characterized in that the above reaction is carried out.
【０００８】また、本発明はｐ−トルイジンおよびｐ−
トルイジン塩酸塩１重量部に対し無水塩化アルミニウム
０．１重量部以上および塩化アンモニウム０．１重量部
以上を加え、２００〜２５０℃にて反応を行わせること
を特徴とするジ−ｐ−トリルアミンの製造方法から構成
される。The present invention also provides p-toluidine and p-toluidine.
To 1 part by weight of toluidine hydrochloride, 0.1 part by weight or more of anhydrous aluminum chloride and 0.1 parts by weight or more of ammonium chloride are added, and the reaction is carried out at 200 to 250 ° C. to obtain di-p-tolylamine. It consists of a manufacturing method.
【０００９】本発明は、有機光導電体の中間体として有
用なジ−ｐ−トリルアミンの効率的な製造方法に関し、
上述した類似化合物であるジフェニルアミンの製造方法
においては全く試みられていない合成条件を採用したジ
−ｐ−トリルアミンの製造方法である。The present invention relates to an efficient method for producing di-p-tolylamine useful as an intermediate for an organic photoconductor,
This is a method for producing di-p-tolylamine that employs synthetic conditions that have never been attempted in the method for producing diphenylamine, which is a similar compound described above.
【００１０】また、本発明は上述の先に本発明者らが提
案したジ−ｐ−トリルアミンの製造方法では、反応温度
は２００℃以下では殆ど反応しないが、反応溶媒を用い
ることにより反応温度を２００℃以下、常圧という、さ
らに緩い反応条件でジ−ｐ−トリルアミンを合成するこ
とができるという新規な製造方法である。Further, in the present invention, in the method for producing di-p-tolylamine previously proposed by the present inventors, the reaction temperature hardly rises at 200 ° C. or lower, but the reaction temperature is changed by using the reaction solvent. It is a novel production method in which di-p-tolylamine can be synthesized under milder reaction conditions of 200 ° C. or lower and normal pressure.
【００１１】反応溶媒としては、ジクロルベンゼン、ト
リクロルベンゼンなどの芳香族ハロゲン化物や沸点１５
０℃以上の溶媒例えばｐ−シメンなどを用いることがで
きる。As the reaction solvent, aromatic halides such as dichlorobenzene and trichlorobenzene and a boiling point of 15
A solvent at 0 ° C. or higher, such as p-cymene, can be used.
【００１２】[0012]
実施例１ ｐ−トルイジン１重量部に対し塩化アルミニウム０．４
重量部、塩化アンモニウム０．４重量部、ｏ−ジクロル
ベンゼン０．６重量部を常圧で撹拌しながら温度を１６
５〜１９５℃で１８時間反応を行わせた後、トルエンで
抽出し、トルエン層を減圧乾固し、２０％酢酸４重量部
で分散した後、ジ−ｐ−トリルアミン粗結晶０．５４重
量部を得た。このジ−ｐ−トリルアミン粗結晶を酢酸エ
チルに溶解し、株式会社島津製作所製ガスクロマトグラ
フＧＣ−８Ａ、同社製クロマトパックＣ−Ｒ６Ａを用い
てｐ−トルイジンとジ−ｐ−トリルアミンのピ−ク面積
を比較したところ９８．３％のジ−ｐ−トリルアミンの
純度が得られた。Example 1 0.4 part of aluminum chloride to 1 part by weight of p-toluidine
Parts by weight, ammonium chloride 0.4 parts by weight, and o-dichlorobenzene 0.6 parts by weight at a temperature of 16 while stirring at atmospheric pressure.
After reacting at 5 to 195 ° C. for 18 hours, extraction with toluene, the toluene layer was evaporated to dryness under reduced pressure and dispersed with 4 parts by weight of 20% acetic acid, and then 0.54 parts by weight of crude di-p-tolylamine crystals. Got The crude crystals of di-p-tolylamine were dissolved in ethyl acetate, and the peak area of p-toluidine and di-p-tolylamine was obtained using Gas Chromatograph GC-8A manufactured by Shimadzu Corporation and Chromatopack C-R6A manufactured by the same company. When compared with each other, a purity of 98.3% of di-p-tolylamine was obtained.
【００１３】実施例２ ｐ−トルイジン１重量部に対し塩化アルミニウム０．４
重量部、塩化アンモニウム０．４重量部、１，２，４−
トリクロルベンゼン０．５重量部を常圧で撹拌しながら
温度を１７５〜１９５℃で１８時間反応を行わせた後、
実施例１と同様に処理したところ、ジ−ｐ−トリルアミ
ン粗結晶０．５５重量部を得た。ジ−ｐトリルアミンの
純度９８．１％であった。Example 2 0.4 part of aluminum chloride to 1 part by weight of p-toluidine
Parts by weight, ammonium chloride 0.4 parts by weight, 1,2,4-
After stirring 0.5 part by weight of trichlorobenzene under normal pressure and reacting at a temperature of 175 to 195 ° C. for 18 hours,
When treated in the same manner as in Example 1, 0.55 parts by weight of di-p-tolylamine crude crystals were obtained. The purity of di-p-tolylamine was 98.1%.
【００１４】実施例３ ｐ−トルイジン１重量部に対し塩化アルミニウム０．４
重量部、塩化アンモニウム０．４重量部、ｐ−シメン
０．５重量部を常圧で撹拌しながら温度を１５０〜１５
５℃で１５時間反応を行わせた後、反応液を分取し、水
で分散し酢酸エチルで抽出した液をガスクロマトグラフ
を用いてｐ−トルイジンとジ−ｐ−トリルアミンのピ−
ク面積を比較したところ、２５％の反応率であった。Example 3 0.4 part of aluminum chloride to 1 part by weight of p-toluidine
Parts by weight, ammonium chloride 0.4 parts by weight, and p-cymene 0.5 parts by weight at a temperature of 150 to 15 while stirring at atmospheric pressure.
After the reaction was carried out at 5 ° C for 15 hours, the reaction solution was separated, dispersed with water and extracted with ethyl acetate. The liquid was extracted with p-toluidine and di-p-tolylamine using a gas chromatograph.
As a result of comparing the black areas, the reaction rate was 25%.
【発明の効果】本発明のジ−ｐ−トリルアミンの製造方
法は、新規な反応条件を採用することによって、効率的
に目的化合物を合成できるという顕著な効果を奏する。INDUSTRIAL APPLICABILITY The method for producing di-p-tolylamine of the present invention has a remarkable effect that a target compound can be efficiently synthesized by adopting novel reaction conditions.
Claims (4)
アルミニウム０．２重量部以上及び溶媒を加え、１５０
℃以上にて反応を行わせることを特徴とするジ−ｐ−ト
リルアミンの製造方法。1. To 1 part by weight of p-toluidine, 0.2 parts by weight or more of anhydrous aluminum chloride and a solvent are added to obtain 150 parts by weight.
A method for producing di-p-tolylamine, which comprises reacting at a temperature of not lower than 0 ° C.
アルミニウム０．２重量部以上及び塩化アンモニウム
０．１重量部以上及び溶媒を加え、１５０℃以上にて反
応を行わせることを特徴とするジ−ｐ−トリルアミンの
製造方法。2. The reaction is carried out at 150 ° C. or higher by adding 0.2 parts by weight or more of anhydrous aluminum chloride, 0.1 parts by weight or more of ammonium chloride and a solvent to 1 part by weight of p-toluidine. A method for producing di-p-tolylamine.
る請求項１または２記載のジ−ｐ−トリルアミンの製造
方法。3. The method for producing di-p-tolylamine according to claim 1, wherein the solvent has a boiling point of 150 ° C. or higher.
れる溶媒である請求項１または２記載のジ−ｐ−トリル
アミンの製造方法。4. The method for producing di-p-tolylamine according to claim 1, wherein the solvent is a solvent selected from aromatic halides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27680592A JPH06100504A (en) | 1992-09-22 | 1992-09-22 | Production of di-para tolylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27680592A JPH06100504A (en) | 1992-09-22 | 1992-09-22 | Production of di-para tolylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06100504A true JPH06100504A (en) | 1994-04-12 |
Family
ID=17574633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27680592A Pending JPH06100504A (en) | 1992-09-22 | 1992-09-22 | Production of di-para tolylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06100504A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218576B1 (en) | 1999-06-04 | 2001-04-17 | Sankio Chemical Co., Ltd. | Process for producing a diarylamine |
-
1992
- 1992-09-22 JP JP27680592A patent/JPH06100504A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6218576B1 (en) | 1999-06-04 | 2001-04-17 | Sankio Chemical Co., Ltd. | Process for producing a diarylamine |
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