JPH0625113A - Production of di-p-tolylamine - Google Patents
Production of di-p-tolylamineInfo
- Publication number
- JPH0625113A JPH0625113A JP11235392A JP11235392A JPH0625113A JP H0625113 A JPH0625113 A JP H0625113A JP 11235392 A JP11235392 A JP 11235392A JP 11235392 A JP11235392 A JP 11235392A JP H0625113 A JPH0625113 A JP H0625113A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- tolylamine
- toluidine
- parts
- aluminum chloride
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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が述
べられている。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 stated that ditolylamine can be produced in a similar manner. This method is carried out under severe reaction conditions of 300 ° C. or higher and 10 atm by adding 0.03 part by weight of aluminum chloride to 1 part by weight of aniline.
【０００４】[0004]
【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.
【０００５】[0005]
【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
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 is characterized in that 0.2 part by weight or more of anhydrous aluminum chloride is added to 1 part by weight of p-toluidine, and the reaction is carried out at 200 to 250 ° C. -Consisting of a method for producing tolylamine.
【０００６】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。In the present invention, more than 0.2 part by weight of anhydrous aluminum chloride and more than 0.1 part by weight of ammonium chloride are added to 1 part by weight of p-toluidine to obtain 200 to 250 parts by weight.
It comprises a method for producing di-p-tolylamine, which is characterized in that the reaction is carried out at a temperature of ° C.
【０００７】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.
【０００８】塩化アルミニウムの量はｐ−トルイジン１
重量部に対して０．２重量部以下では非常に収率が低
く、望ましくは０．４重量部程度がよい。これ以上多い
量で使用しても、収率の上昇はそれ程期待できない。The amount of aluminum chloride is p-toluidine 1
If the amount is 0.2 parts by weight or less, the yield is very low, and preferably about 0.4 parts by weight. Even if it is used in a larger amount, the increase in yield cannot be expected so much.
【０００９】塩化アンモニウムの量はｐ−トルイジン１
重量部に対して０．１重量部以上が用いられる。The amount of ammonium chloride is p-toluidine 1
0.1 parts by weight or more is used with respect to parts by weight.
【００１０】反応温度は２００℃以下では殆ど反応せ
ず、また、２５０℃以上では反応生成物の分解が始まる
ことになり、最も望ましい温度は２３０〜２４０℃であ
る。When the reaction temperature is 200 ° C. or lower, almost no reaction occurs, and when the reaction temperature is 250 ° C. or higher, decomposition of the reaction product starts, and the most desirable temperature is 230 to 240 ° C.
【００１１】原料のｐ−トルイジンは場合によりｐ−ト
ルイジン塩酸塩と混合使用することができる。The raw material p-toluidine can be optionally mixed with p-toluidine hydrochloride.
【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重量部をオ−トクレ−
ブに入れ、撹拌しながら温度を２２０℃から２４０℃、
圧力約２気圧で６時間反応を行わせた後、１８％塩酸３
重量部で反応物を分散した後、ろ過した。得られた粗結
晶を水で十分に洗浄し、乾燥してジ−ｐ−トリルアミン
粗結晶０．５６重量部を得た。このジ−ｐ−トリルアミ
ン粗結晶をエチルアルコ−ルに溶解した後、ろ過したろ
液を株式会社島津製作所製ガスクロマトグラフＧＣ−８
Ａ、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９９．６％のジ−ｐ−トリルアミンの純度が得ら
れた。また、塩酸分散ろ液および水洗液から０．３８重
量部のｐ−トルイジンが回収された。Example 1 0.4 part of aluminum chloride to 1 part by weight of p-toluidine
Parts by weight, 0.4 parts by weight of ammonium chloride
Put in a pot and stir at a temperature of 220 ° C to 240 ° C,
After reacting at a pressure of about 2 atm for 6 hours, 18% hydrochloric acid 3
The reaction product was dispersed in parts by weight and then filtered. The obtained crude crystals were thoroughly washed with water and dried to obtain 0.56 parts by weight of crude di-p-tolylamine crystals. This crude di-p-tolylamine crystal was dissolved in ethyl alcohol, and the filtered filtrate was filtered by a gas chromatograph GC-8 manufactured by Shimadzu Corporation.
A, when the peak areas of p-toluidine and di-p-tolylamine were compared using Chromatopack C-R6A manufactured by the same company, a purity of di-p-tolylamine of 99.6% was obtained. In addition, 0.38 parts by weight of p-toluidine was recovered from the hydrochloric acid dispersion filtrate and the water washing liquid.
【００１３】実施例２ ｐ−トルイジン１重量部に対して塩化アルミニウム０．
２重量部、塩化アンモニウム０．１重量部をオ−トクレ
−ブに入れ、撹拌しながら温度を２３０℃から２４０
℃、圧力約２気圧で６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
０．３７重量部、ジ−ｐ−トリルアミンの粗結晶の純度
９９．４％、また、ｐ−トルイジンの回収量は０．５６
重量部であった。Example 2 1 part by weight of p-toluidine was used and aluminum chloride was added in an amount of 0.
2 parts by weight and 0.1 part by weight of ammonium chloride were put in an autoclave, and the temperature was changed from 230 to 240 while stirring.
After the reaction was carried out at a temperature of about 2 atm for 6 hours, Example 1
When treated in the same manner as in Example 3, 0.37 parts by weight of crude di-p-tolylamine crystals, purity 99.4% of crude di-p-tolylamine crystals, and a recovery amount of p-toluidine of 0.56.
It was part by weight.
【００１４】実施例３ ｐ−トルイジン１重量部に対して塩化アルミニウム０．
４重量部のみをオ−トクレ−ブに入れ撹拌しながら温度
を２１０℃から２４０℃、圧力約２気圧で６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０．３２重量部、ジ−ｐ−トリル
アミンの粗結晶の純度９５．８％、また、ｐ−トルイジ
ンの回収量０．６１重量部であった。Example 3 One part by weight of p-toluidine was used and aluminum chloride was added in an amount of 0.
Only 4 parts by weight was put into an autoclave and reacted with stirring at a temperature of 210 ° C. to 240 ° C. and a pressure of about 2 atm for 6 hours, and then treated in the same manner as in Example 1, whereupon di-p
The crude crystals of tolylamine were 0.32 parts by weight, the purity of the crude crystals of di-p-tolylamine was 95.8%, and the recovery amount of p-toluidine was 0.61 parts by weight.
【００１５】実施例４ ｐ−トルイジン１重量部に対して塩化アルミニウム０．
４重量部、塩化アンモニウム０．４重量部を常圧で撹拌
しながら温度を２００℃から２４０℃で８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０．４４重量部、ジ−ｐ−トリルア
ミンの粗結晶の純度９８．０％、また、ｐ−トルイジン
の回収量０．５０重量部であった。Example 4 To 1 part by weight of p-toluidine, aluminum chloride was added.
4 parts by weight of ammonium chloride and 0.4 parts by weight of ammonium chloride were reacted at a temperature of 200 ° C. to 240 ° C. for 8 hours with stirring under normal pressure, and then treated in the same manner as in Example 1, whereupon di-p
The crude crystals of tolylamine were 0.44 parts by weight, the purity of the crude crystals of di-p-tolylamine was 98.0%, and the recovered amount of p-toluidine was 0.50 parts by weight.
【００１６】比較例１ 英国特許第６４４，９３８号に記載の反応条件に準じ
て、ｐ−トルイジン１重量部に対して塩化アルミニウム
０．０３重量部をオ−トクレ−ブに入れ撹拌しながら温
度を３００℃から３２０℃、圧力約１１気圧で６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０．１５重量部、ジ−ｐ−ト
リルアミンの粗結晶の純度９４．７％、また、ｐ−トル
イジンの回収量０．４１重量部であった。Comparative Example 1 According to the reaction conditions described in British Patent No. 644,938, 0.03 parts by weight of aluminum chloride was added to 1 part by weight of p-toluidine in an autoclave and the temperature was changed with stirring. Was reacted at 300 ° C. to 320 ° C. and a pressure of about 11 atm for 6 hours, and then treated in the same manner as in Example 1, to obtain 0.15 parts by weight of di-p-tolylamine crude crystals and di-p-tolylamine. The crude crystal purity was 94.7%, and the amount of p-toluidine recovered was 0.41 part by weight.
【００１７】[0017]
【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 (2)
アルミニウム０．２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。1. 200-250 by adding 0.2 part by weight or more of anhydrous aluminum chloride to 1 part by weight of p-toluidine.
A method for producing di-p-tolylamine, which comprises reacting at 0 ° C.
アルミニウム０．２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。2. Di-characterized in that 0.2 part by weight or more of anhydrous aluminum chloride and 0.1 part by weight or more of ammonium chloride are added to 1 part by weight of p-toluidine and the reaction is carried out at 200 to 250 ° C. -A method for producing p-tolylamine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11235392A JPH0625113A (en) | 1992-04-06 | 1992-04-06 | Production of di-p-tolylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11235392A JPH0625113A (en) | 1992-04-06 | 1992-04-06 | Production of di-p-tolylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0625113A true JPH0625113A (en) | 1994-02-01 |
Family
ID=14584576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11235392A Pending JPH0625113A (en) | 1992-04-06 | 1992-04-06 | Production of di-p-tolylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0625113A (en) |
-
1992
- 1992-04-06 JP JP11235392A patent/JPH0625113A/en active Pending
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