JPH10287656A - Production of 2-imidazolines - Google Patents
Production of 2-imidazolinesInfo
- Publication number
- JPH10287656A JPH10287656A JP9873997A JP9873997A JPH10287656A JP H10287656 A JPH10287656 A JP H10287656A JP 9873997 A JP9873997 A JP 9873997A JP 9873997 A JP9873997 A JP 9873997A JP H10287656 A JPH10287656 A JP H10287656A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- imidazolines
- compound
- pressure
- ethylenediamine
- 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.)
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、２−イミダゾリン
類の製造法に関する。一般に、２−イミダゾリン類は、
各種農薬、医薬又は染料中間体として極めて有用な化合
物である。TECHNICAL FIELD The present invention relates to a method for producing 2-imidazolines. Generally, 2-imidazolines are
It is a compound extremely useful as an intermediate for various agricultural chemicals, medicines or dyes.
【０００２】[0002]
【従来の技術】ポリアミン及びニトリル化合物を原料と
する２−イミダゾリン類の製造としては、以下の方法が
知られている。2. Description of the Related Art The following processes are known for producing 2-imidazolines from polyamine and nitrile compounds as raw materials.
【０００３】特公昭３９−２４９６５号公報には、硫黄
の存在下で反応させる方法が記載されている。硫黄を触
媒とする方法は、反応中に極めて毒性の高い硫化水素が
副生するほか、イミダゾリンからイミダゾールを製造す
る場合、残存する硫黄が脱水素触媒を被毒し、反応を阻
害する等の問題があった。[0003] Japanese Patent Publication No. 39-24965 discloses a method of reacting in the presence of sulfur. In the method using sulfur as a catalyst, extremely toxic hydrogen sulfide is by-produced during the reaction, and when producing imidazole from imidazoline, the remaining sulfur poisons the dehydrogenation catalyst and inhibits the reaction. was there.
【０００４】この問題を解決するために、特公平５−３
９９４３号公報には、酢酸銅、塩化銅等の銅塩触媒、特
開昭６２−１９５３６９号公報には、酢酸亜鉛、塩化亜
鉛等の亜鉛塩を触媒とする方法が記載されている。銅塩
触媒、亜鉛塩触媒を使うと、硫化水素の副生はみられな
いものの、銅イオン、亜鉛イオン等の不純物が反応系に
入るため、生成物がイミダゾリンの金属錯体となり、精
製を必要とする。また、イミダゾリンからイミダゾール
を製造する場合、残存する金属イオンが脱水素触媒を被
毒し、収率が低下する等の問題があった。In order to solve this problem, Japanese Patent Publication No. 5-3
No. 9943 describes a method using a copper salt catalyst such as copper acetate or copper chloride, and JP-A No. 62-195369 describes a method using a zinc salt such as zinc acetate or zinc chloride as a catalyst. When a copper salt catalyst or a zinc salt catalyst is used, no by-products of hydrogen sulfide are found, but impurities such as copper ions and zinc ions enter the reaction system, so that the product becomes a metal complex of imidazoline and requires purification. I do. Further, when imidazole is produced from imidazoline, there is a problem that residual metal ions poison the dehydrogenation catalyst and the yield is reduced.
【０００５】[0005]
【発明が解決しようとする課題】上記したように従来の
方法では、硫化水素が副生する、残存する硫黄が反応を
阻害する、生成物がイミダゾリンの金属錯体となり精製
を必要とする等の問題があり、イミダゾリンを効率よく
製造するには十分ではない。したがって、これらの欠点
を解消した方法、すなわち、分離、精製が必要となる硫
黄、金属塩を触媒とせず、硫化水素を副生しない方法の
開発が望まれていた。As described above, in the conventional method, there are problems such as by-produced hydrogen sulfide, residual sulfur inhibiting the reaction, and the product becoming a metal complex of imidazoline and requiring purification. However, it is not enough to produce imidazoline efficiently. Therefore, it has been desired to develop a method that solves these drawbacks, that is, a method that does not use sulfur or a metal salt that requires separation and purification as a catalyst and that does not generate hydrogen sulfide as a by-product.
【０００６】[0006]
【課題を解決するための手段】本発明者らは、イミダゾ
リン類の製造法について鋭意検討をした結果、触媒とし
てアンモニウム塩を使用することによって、硫化水素の
発生もなく、分離、精製を必要としないイミダゾリン類
の製造が可能であるという新規な事実を見出し、本発明
を完成するに至った。Means for Solving the Problems As a result of intensive studies on a method for producing imidazolines, the present inventors have found that by using an ammonium salt as a catalyst, hydrogen sulfide is not generated, and separation and purification are required. The present inventors have found a novel fact that imidazolines can be produced without using the same, and have completed the present invention.
【０００７】すなわち、本発明は、ポリアミンとニトリ
ル化合物を反応させて２−イミダゾリン類を製造する際
に、塩化アンモニウム及び／又はアミンの塩酸塩の存在
下で反応を行うことを特徴とする２−イミダゾリン類の
製造法である。That is, the present invention is characterized in that when producing a 2-imidazoline by reacting a polyamine with a nitrile compound, the reaction is carried out in the presence of ammonium chloride and / or a hydrochloride of an amine. This is a method for producing imidazolines.
【０００８】以下に本発明を詳細に説明する。Hereinafter, the present invention will be described in detail.
【０００９】本発明の方法において使用される触媒は、
塩化アンモニウム及び／又はアミンの塩酸塩である。The catalyst used in the process of the present invention is
Hydrochloride of ammonium chloride and / or amine.
【００１０】アミンとしては特に制限はないが、あえて
例示すると、メチルアミン、ジメチルアミン、トリメチ
ルアミン、エチルアミン、ジエチルアミン、トリエチル
アミン等の脂肪族アミン類、ピペリジン、ピロリジン、
シクロヘキシルアミン等の脂環式アミン類、ピリジン、
アニリン等の芳香族アミン類、エチレンジアミン、ジエ
チレントリアミン、プロパンジアミン等のポリアミン類
等が挙げられる。The amine is not particularly limited, but examples thereof include aliphatic amines such as methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine and triethylamine, piperidine, pyrrolidine, and the like.
Alicyclic amines such as cyclohexylamine, pyridine,
Examples thereof include aromatic amines such as aniline, and polyamines such as ethylenediamine, diethylenetriamine, and propanediamine.
【００１１】本発明の方法においては、反応原料として
ポリアミンを使用するので、反応中に塩化水素等を添加
してアンモニウム塩としても良いし、また反応中にアン
モニアが発生するため、反応系中に塩化水素を添加して
反応しても良い。In the method of the present invention, since polyamine is used as a reaction raw material, hydrogen chloride or the like may be added during the reaction to form an ammonium salt, and ammonia is generated during the reaction. The reaction may be performed by adding hydrogen chloride.
【００１２】本発明の方法において、使用される触媒の
量は、触媒の種類によって異なるため明示することは困
難ではあるが、通常ポリアミンに対して０．０１重量部
〜１００重量部の範囲である。例えば、触媒として塩化
アンモニウムを用いた場合、好ましくは０．０５重量部
〜５０重量部の範囲、さらに好ましくは０．１重量部〜
２０重量部の範囲である。０．０１重量部以下では反応
の進行が遅いため実用的ではなく、１００重量部を越え
て過剰に加えても触媒を増やした効果は小さい。In the method of the present invention, it is difficult to specify the amount of the catalyst to be used because it differs depending on the type of the catalyst, but it is usually in the range of 0.01 to 100 parts by weight based on the polyamine. . For example, when ammonium chloride is used as the catalyst, the amount is preferably in the range of 0.05 to 50 parts by weight, more preferably 0.1 to 50 parts by weight.
It is in the range of 20 parts by weight. If the amount is less than 0.01 part by weight, the progress of the reaction is slow, so that it is not practical. Even if it exceeds 100 parts by weight, the effect of increasing the catalyst is small.
【００１３】本発明の方法において、使用される原料
は、ポリアミンとニトリル化合物である。ポリアミンは
下記式（１） Ｈ2ＮＣＨＲ1ＣＨＲ2ＮＨＲ3 （１） （式中、Ｒ1、Ｒ2、Ｒ3は各々独立して水素、脂肪族、
芳香脂肪族又は芳香族の基を意味し、それらは官能基を
含んでいても良い。）で示される化合物であり、ニトリ
ル化合物は下記式（２） Ｒ4ＣＮ （２） （式中、Ｒ4は水素、脂肪族、芳香脂肪族又は芳香族の
基を意味する。）で示される化合物である。In the method of the present invention, the raw materials used are a polyamine and a nitrile compound. The polyamine is represented by the following formula (1) H 2 NCHR 1 CHR 2 NHR 3 (1) (wherein R 1 , R 2 and R 3 are each independently hydrogen, aliphatic,
An araliphatic or aromatic group is meant, which may contain functional groups. Wherein the nitrile compound is represented by the following formula (2) R 4 CN (2) (wherein R 4 represents hydrogen, an aliphatic, araliphatic or aromatic group). Compound.
【００１４】ポリアミンとしては、エチレンジアミン、
ジエチレントリアミン、トリエチレンテトラミン、テト
ラエチレンペンタミン、ペンタエチレンヘキサミン等の
エチレンアミン類、プロピレンジアミン、ブチレンジア
ミン、ペンチレンジアミン、ヘキサレンジアミン、オク
チレンジアミン、ノニレンジアミン、デシレンジアミ
ン、シクロヘキシルエチレンジアミン、ベンジルエチレ
ンジアミン、フェニルエチレンジアミン、メトキシフェ
ニルエチレンジアミン、ジメチルフェニルエチレンジア
ミン、トリルエチレンジアミン、Ｎ−ブチルエチレンジ
アミン、Ｎ−イソブチルエチレンジアミン、Ｎ−メチル
エチレンジアミン、Ｎ−エチルエチレンジアミン、Ｎ−
シクロヘキシルエチレンジアミン、Ｎ−ベンジルエチレ
ンジアミン、Ｎ−フェニルエチレンジアミン、Ｎ−メト
キシフェニルエチレンジアミン、Ｎ−ジメチルフェニル
エチレンジアミン、Ｎ−トリルエチレンジアミン等が例
示される。As the polyamine, ethylenediamine,
Ethyleneamines such as diethylenetriamine, triethylenetetramine, tetraethylenepentamine and pentaethylenehexamine, propylenediamine, butylenediamine, pentylenediamine, hexadiamine, octylenediamine, nonylenediamine, desilylenediamine, cyclohexylethylenediamine, benzyl Ethylenediamine, phenylethylenediamine, methoxyphenylethylenediamine, dimethylphenylethylenediamine, tolylethylenediamine, N-butylethylenediamine, N-isobutylethylenediamine, N-methylethylenediamine, N-ethylethylenediamine, N-
Examples thereof include cyclohexylethylenediamine, N-benzylethylenediamine, N-phenylethylenediamine, N-methoxyphenylethylenediamine, N-dimethylphenylethylenediamine, and N-tolylethylenediamine.
【００１５】また、ニトリル化合物としては、アセトニ
トリル、プロピオニトリル、イソブチロニトリル、２−
エチルヘキシロニトリル、ラウロニトリル、ステアロニ
トリル、シクロヘキシルニトリル、フェニルアセトニト
リル、フェニルプロピオニトリル、ベンゾニトリル、メ
チルベンゾニトリル、ジメチルベンゾニトリル、メトキ
シベンゾニトリル、ジメトキシベンゾニトリル、ナフト
ニトリル、シアノピリジン、マロンニトリル、アジポニ
トリル、フタロニトリル、ジシアノジフェニル、１，４
−ジシアノブタン等が例示される。The nitrile compounds include acetonitrile, propionitrile, isobutyronitrile, 2-
Ethylhexylonitrile, lauronitrile, stearonitrile, cyclohexylnitrile, phenylacetonitrile, phenylpropionitrile, benzonitrile, methylbenzonitrile, dimethylbenzonitrile, methoxybenzonitrile, dimethoxybenzonitrile, naphthonitrile, cyanopyridine, malonnitrile, Adiponitrile, phthalonitrile, dicyanodiphenyl, 1,4
-Dicyanobutane and the like.
【００１６】本発明の方法において、ポリアミンとニト
リル化合物は化学当量又は一方の過剰で反応を行うこと
ができる。In the method of the present invention, the reaction between the polyamine and the nitrile compound can be carried out in a chemical equivalent or an excess of one.
【００１７】本発明の方法において、反応温度は通常１
００〜３００℃の範囲であるが、１５０〜２５０℃で行
うことが好ましい。１００℃未満の反応温度では、反応
速度は非常に遅いため実用的でなく、３００℃を越える
反応温度では、原料の分解が生じ、イミダゾリン類の収
率が低下する場合がある。In the method of the present invention, the reaction temperature is usually 1
Although it is the range of 00-300 ° C, it is preferred to carry out at 150-250 ° C. If the reaction temperature is lower than 100 ° C., the reaction rate is extremely slow, which is not practical. If the reaction temperature is higher than 300 ° C., the raw material is decomposed, and the yield of imidazolines may decrease.
【００１８】本発明の方法は、通常液相で実施する。The process according to the invention is usually carried out in the liquid phase.
【００１９】本発明の方法において、反応は、原料を液
状に保てればよく、常圧，加圧又は減圧下で行うことが
できる。この反応では、反応中にアンモニアが生成する
ため反応圧力が上昇するが、このアンモニアは反応途中
で除去することもできるし、反応が終了してから除去す
ることもできる。反応温度が原料の沸点を越えている場
合は、加圧下で反応を実施する、凝縮器を設け原料を液
化する、又は原料を少しずつ供給する等の方法をとるこ
とができる。In the method of the present invention, the reaction may be carried out under normal pressure, increased pressure or reduced pressure as long as the raw materials are kept in a liquid state. In this reaction, the reaction pressure increases due to the generation of ammonia during the reaction. However, this ammonia can be removed during the reaction, or can be removed after the reaction is completed. When the reaction temperature exceeds the boiling point of the raw material, a method of performing the reaction under pressure, providing a condenser to liquefy the raw material, or supplying the raw material little by little can be employed.
【００２０】本発明の方法において、溶媒を使用しても
しなくても良い。溶媒としては、反応条件に不活性なも
のであれば特に制限はなく、水等、イミダゾリン類を分
解するものの使用は好ましくない。In the method of the present invention, a solvent may or may not be used. The solvent is not particularly limited as long as it is inert to the reaction conditions. Use of a solvent that decomposes imidazolines, such as water, is not preferred.
【００２１】本発明の方法は、連続反応で実施しても、
回分反応、半回分反応で実施しても良い。また、固定床
でも懸濁床でも反応できる。The process of the present invention can be carried out in a continuous reaction,
The reaction may be performed as a batch reaction or a semi-batch reaction. In addition, the reaction can be carried out using a fixed bed or a suspension bed.
【００２２】本発明の方法において、反応生成物のイミ
ダゾリン類は、精製しても、精製せずに脱水素してイミ
ダゾール類としても良い。イミダゾリン類の精製方法
は、蒸留、再結晶等の種々の方法が知られているが、ど
の方法を用いても一向に差し支えない。In the method of the present invention, imidazolines as reaction products may be purified or dehydrogenated to imidazoles without purification. Various methods such as distillation and recrystallization are known as a method for purifying imidazolines, but any method may be used.
【００２３】[0023]
【発明の効果】本発明によれば、硫化水素の発生もな
く、また分離、精製が必要な金属イオンを生成しないイ
ミダゾリン類を効率よく製造することができるため、工
業上極めて有意義である。According to the present invention, imidazolines that do not generate hydrogen sulfide and that do not generate metal ions that need to be separated and purified can be efficiently produced, which is extremely industrially significant.
【００２４】[0024]
【実施例】以下、本発明の方法を実施例により説明する
が、本発明はこれらに限定されるものではない。EXAMPLES The method of the present invention will be described below with reference to examples, but the present invention is not limited to these examples.
【００２５】実施例１ ２００ｍｌのステンレス製オートクレーブにエチレンジ
アミン４８．５ｇ（０．８１モル）、アセトニトリル３
６．８ｇ、塩化アンモニウム２．４ｇ及びメタノール３
４．７ｇを入れ、窒素置換した後、１８０℃に加熱し
た。反応圧力が２．５ＭＰａ以上になったら脱圧を行
い、圧力を下げ、６時間反応した。反応終了後、室温ま
で冷却し、ガスクロマトグラフィーで分析したところ、
エチレンジアミンの転化率９８％，２−メチルイミダゾ
リンの選択率は９８％であった。Example 1 In a 200 ml stainless steel autoclave, 48.5 g (0.81 mol) of ethylenediamine, acetonitrile 3
6.8 g, ammonium chloride 2.4 g and methanol 3
After 4.7 g of the mixture was charged and purged with nitrogen, the mixture was heated to 180 ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography.
The conversion of ethylenediamine was 98%, and the selectivity for 2-methylimidazoline was 98%.
【００２６】実施例２ ２００ｍｌのステンレス製オートクレーブにエチレンジ
アミン４８．１ｇ（０．８０モル）、アセトニトリル３
６．１ｇ、塩化アンモニウム２．４ｇ及びメタノール３
４．５ｇを入れ、窒素置換した後、２００℃に加熱し
た。反応圧力が２．５ＭＰａ以上になったら脱圧を行
い、圧力を下げ、３時間反応した。反応終了後、室温ま
で冷却し、ガスクロマトグラフィーで分析したところ、
エチレンジアミンの転化率１００％，２−メチルイミダ
ゾリンの選択率は９６％であった。Example 2 In a 200 ml stainless steel autoclave, 48.1 g (0.80 mol) of ethylenediamine, acetonitrile 3
6.1 g, ammonium chloride 2.4 g and methanol 3
After 4.5 g was added and the atmosphere was replaced with nitrogen, the mixture was heated to 200 ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography.
The conversion of ethylenediamine was 100%, and the selectivity for 2-methylimidazoline was 96%.
【００２７】実施例３ ２００ｍｌのステンレス製オートクレーブにエチレンジ
アミン４８．１ｇ（０．８０モル）、アセトニトリル３
６．１ｇ、エチレンジアミンの塩酸塩４．３ｇ及びメタ
ノール３５．７ｇを入れ、窒素置換した後、１８０℃に
加熱した。反応圧力が２．５ＭＰａ以上になったら脱圧
を行い、圧力を下げ、６時間反応した。反応終了後、室
温まで冷却し、ガスクロマトグラフィーで分析したとこ
ろ、エチレンジアミンの転化率９７％，２−メチルイミ
ダゾリンの選択率は９６％であった。Example 3 In a 200 ml stainless steel autoclave, 48.1 g (0.80 mol) of ethylenediamine, acetonitrile 3
6.1 g, 4.3 g of hydrochloride of ethylenediamine and 35.7 g of methanol were added, and the mixture was purged with nitrogen and then heated to 180 ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography. As a result, the conversion of ethylenediamine was 97%, and the selectivity of 2-methylimidazoline was 96%.
【００２８】実施例４ ２００ｍｌのステンレス製オートクレーブにプロピレン
ジアミン５０．０ｇ（０．６７モル）、プロピオニトリ
ル３３．５ｇ、塩化アンモニウム２．０ｇ及びメタノー
ル３７．０ｇを入れ、窒素置換した後、１８０℃に加熱
した。反応圧力が２．５ＭＰａ以上になったら脱圧を行
い、圧力を下げ、６時間反応した。反応終了後、室温ま
で冷却し、ガスクロマトグラフィーで分析したところ、
プロピレンジアミンの転化率９０％，２−エチル−４
（５）−メチルイミダゾリンの選択率は９８％であっ
た。Example 4 A 200 ml stainless steel autoclave was charged with 50.0 g (0.67 mol) of propylenediamine, 33.5 g of propionitrile, 2.0 g of ammonium chloride and 37.0 g of methanol, and after purging with nitrogen, 180 Heated to ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 6 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography.
90% conversion of propylene diamine, 2-ethyl-4
The selectivity for (5) -methylimidazoline was 98%.
【００２９】実施例５ ２００ｍｌのステンレス製オートクレーブにプロピレン
ジアミン５０．０ｇ（０．６７モル）、プロピオニトリ
ル３３．５ｇ、塩化アンモニウム２．０ｇ及びメタノー
ル３７．０ｇを入れ、窒素置換した後、２００℃に加熱
した。反応圧力が２．５ＭＰａ以上になったら脱圧を行
い、圧力を下げ、３時間反応した。反応終了後、室温ま
で冷却し、ガスクロマトグラフィーで分析したところ、
プロピレンジアミンの転化率９５％，２−エチル−４
（５）−メチルイミダゾリンの選択率は９７％であっ
た。Example 5 A 200 ml stainless steel autoclave was charged with 50.0 g (0.67 mol) of propylenediamine, 33.5 g of propionitrile, 2.0 g of ammonium chloride and 37.0 g of methanol. Heated to ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography.
95% conversion of propylene diamine, 2-ethyl-4
The selectivity for (5) -methylimidazoline was 97%.
【００３０】実施例６ ２００ｍｌのステンレス製オートクレーブにエチレンジ
アミン３０．１ｇ（０．５０モル）、ベンゾニトリル４
６．９ｇ、塩化アンモニウム３．０ｇ及びメタノール３
１．９ｇを入れ、窒素置換した後、１８０℃に加熱し
た。反応圧力が２．５ＭＰａ以上になったら脱圧を行
い、圧力を下げ、７時間反応した。反応終了後、室温ま
で冷却し、ガスクロマトグラフィーで分析したところ、
エチレンジアミンの転化率９８％，２−フェニルイミダ
ゾリンの選択率は９８％であった。Example 6 30.1 g (0.50 mol) of ethylenediamine and benzonitrile 4 were placed in a 200 ml stainless steel autoclave.
6.9 g, ammonium chloride 3.0 g and methanol 3
1.9 g was added, and after purging with nitrogen, the mixture was heated to 180 ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 7 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography.
The conversion of ethylenediamine was 98%, and the selectivity for 2-phenylimidazoline was 98%.
【００３１】実施例７ ２００ｍｌのステンレス製オートクレーブにエチレンジ
アミン３０．１ｇ（０．５０モル）、ベンゾニトリル４
６．９ｇ、塩化アンモニウム３．０ｇ及びメタノール３
５．３ｇを入れ、窒素置換した後、２００℃に加熱し
た。反応圧力が２．５ＭＰａ以上になったら脱圧を行
い、圧力を下げ、５時間反応した。反応終了後、室温ま
で冷却し、ガスクロマトグラフィーで分析したところ、
エチレンジアミンの転化率９９％，２−フェニルイミダ
ゾリンの選択率は９７％であった。Example 7 30.1 g (0.50 mol) of ethylenediamine and benzonitrile 4 were placed in a 200 ml stainless steel autoclave.
6.9 g, ammonium chloride 3.0 g and methanol 3
After adding 5.3 g and purging with nitrogen, the mixture was heated to 200 ° C. When the reaction pressure became 2.5 MPa or more, the pressure was released, the pressure was reduced, and the reaction was performed for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and analyzed by gas chromatography.
The conversion of ethylenediamine was 99%, and the selectivity for 2-phenylimidazoline was 97%.
Claims (6)
て２−イミダゾリン類を製造する際に、塩化アンモニウ
ム及び／又はアミンの塩酸塩の存在下で反応を行うこと
を特徴とする２−イミダゾリン類の製造法。1. A method for producing 2-imidazolines, which comprises reacting a polyamine with a nitrile compound to produce 2-imidazolines, wherein the reaction is carried out in the presence of ammonium chloride and / or a hydrochloride of an amine. Law.
化合物であることを特徴とする請求項１に記載の製造
法。 Ｈ2ＮＣＨＲ1ＣＨＲ2ＮＨＲ3 （１） （式中、Ｒ1、Ｒ2、Ｒ3は各々独立して水素、脂肪族、
芳香脂肪族又は芳香族の基を意味し、それらは官能基を
含んでいても良い。）2. The method according to claim 1, wherein the polyamine is a compound represented by the following formula (1). H 2 NCHR 1 CHR 2 NHR 3 (1) (wherein, R 1 , R 2 and R 3 are each independently hydrogen, aliphatic,
An araliphatic or aromatic group is meant, which may contain functional groups. )
ジアミンであることを特徴とする請求項２に記載の製造
法。3. The method according to claim 2, wherein the compound represented by the formula (1) is ethylenediamine.
ンジアミンであることを特徴とする請求項２に記載の製
造法。4. The method according to claim 2, wherein the compound represented by the formula (1) is propylene diamine.
れる化合物であることを特徴とする請求項１乃至請求項
４のいずれかに記載の製造法。 Ｒ4ＣＮ （２） （式中、Ｒ4は水素、脂肪族、芳香脂肪族又は芳香族の
基を意味する。）5. The method according to claim 1, wherein the nitrile compound is a compound represented by the following formula (2). R 4 CN (2) (wherein, R 4 represents a hydrogen, aliphatic, araliphatic or aromatic group.)
請求項１乃至請求項５のいずれかに記載の製造法。6. The production method according to claim 1, wherein the reaction is carried out in a liquid phase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09873997A JP4210795B2 (en) | 1997-04-16 | 1997-04-16 | 2-Imidazoline production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP09873997A JP4210795B2 (en) | 1997-04-16 | 1997-04-16 | 2-Imidazoline production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH10287656A true JPH10287656A (en) | 1998-10-27 |
| JP4210795B2 JP4210795B2 (en) | 2009-01-21 |
Family
ID=14227870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP09873997A Expired - Fee Related JP4210795B2 (en) | 1997-04-16 | 1997-04-16 | 2-Imidazoline production method |
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| Country | Link |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003313172A (en) * | 2002-04-23 | 2003-11-06 | Tosoh Corp | Method for producing n-substituted imidazole |
| CN104402820A (en) * | 2014-12-02 | 2015-03-11 | 千辉药业（安徽）有限责任公司 | Synthesis method of 1-ethyl-2-methylimidazoline |
-
1997
- 1997-04-16 JP JP09873997A patent/JP4210795B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003313172A (en) * | 2002-04-23 | 2003-11-06 | Tosoh Corp | Method for producing n-substituted imidazole |
| CN104402820A (en) * | 2014-12-02 | 2015-03-11 | 千辉药业（安徽）有限责任公司 | Synthesis method of 1-ethyl-2-methylimidazoline |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4210795B2 (en) | 2009-01-21 |
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