JPH0717935A - Production of 3-aminopropionitrile - Google Patents
Production of 3-aminopropionitrileInfo
- Publication number
- JPH0717935A JPH0717935A JP19094693A JP19094693A JPH0717935A JP H0717935 A JPH0717935 A JP H0717935A JP 19094693 A JP19094693 A JP 19094693A JP 19094693 A JP19094693 A JP 19094693A JP H0717935 A JPH0717935 A JP H0717935A
- Authority
- JP
- Japan
- Prior art keywords
- ammonia
- aminopropionitrile
- acrylonitrile
- reaction
- present
- 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.)
- Granted
Links
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、アクリロニトリルとア
ンモニアとを反応させることによって、３−アミノプロ
ピオニトリルを製造する方法に関するものである。３−
アミノプロピオニトリルは、アミノ酸原料、医農薬原
料、高分子原料などとして広い利用範囲を持つ化合物で
ある。TECHNICAL FIELD The present invention relates to a method for producing 3-aminopropionitrile by reacting acrylonitrile with ammonia. 3-
Aminopropionitrile is a compound having a wide range of applications as a raw material for amino acids, a raw material for medicines and agricultural chemicals, a raw material for polymers, and the like.
【０００２】[0002]
【従来の技術】３−アミノプロピオニトリルの製造法に
ついては、従来から種々の方法が知られている。例え
ば、アクリロニトリルとアンモニア水を高温短時間で反
応させる方法（Ｅ．Ｍ．Ｓｍｏｌｉｎ ｅｔ ａｌ．，
Ｉｎｄ．Ｅｎｇ．Ｃｈｅｍ．，５０ １１１５ （１９
５８））、アクリロニトリルと液体アンモニアとをラネ
ー触媒共存下反応させる方法（特公昭４５−３９０８５
号公報）、アクリロニトリルとアンモニアとをメタノー
ル溶媒中で反応させる方法（Ｄ．Ｓ．Ｎｅｓｔｅｒｕ
ｋ，Ｐｒｚｅｍｙｓｌ Ｃｈｅｍ．，４４ ８５ （１
９６５））、またはアクリロニトリルと液体アンモニア
とを第３級ブタノール溶媒中で反応させる方法（米国特
許第２７４２４９１号明細書）などが提案されている。2. Description of the Related Art Conventionally, various methods have been known for producing 3-aminopropionitrile. For example, a method of reacting acrylonitrile and aqueous ammonia at high temperature in a short time (EM Smolin et al.,
Ind. Eng. Chem. , 50 1115 (19
58)), a method of reacting acrylonitrile and liquid ammonia in the presence of a Raney catalyst (Japanese Patent Publication No. 45-39085).
Japanese Patent Publication), a method of reacting acrylonitrile and ammonia in a methanol solvent (DS Nesteru).
k, Przemysl Chem. , 44 85 (1
965)), or a method of reacting acrylonitrile and liquid ammonia in a tertiary butanol solvent (US Pat. No. 2,742,491) and the like.
【０００３】しかしながら、アクリロニトリルとアンモ
ニア水あるいは液体アンモニアとを反応させる方法にお
いて、３−アミノプロピオニトリルを効率よく得るに
は、アクリロニトリルとアンモニアのモル比をアンモニ
ア大過剰で反応させることが必要である。また、溶媒と
してメタノールなど第一級アルコール類を用いると、ア
ルコールとアクリロニトリルの反応により３−アルコキ
シプロピオニトリルが副生し、３−アミノプロピオニト
リルの収率が低下するとともに、蒸留精製工程が極めて
複雑になる。さらに、第３級ブタノールなど第三級アル
コール類を溶媒に用いる方法では、アルコールの融点が
上昇し室温で固体状態となるため、操作性が著しく悪化
するなど、工業的に実施する方法としては改善すべき問
題があった。However, in the method of reacting acrylonitrile with aqueous ammonia or liquid ammonia, in order to efficiently obtain 3-aminopropionitrile, it is necessary to react acrylonitrile with ammonia in a large molar excess of ammonia. . Moreover, when a primary alcohol such as methanol is used as a solvent, 3-alkoxypropionitrile is by-produced by the reaction of alcohol and acrylonitrile, and the yield of 3-aminopropionitrile is reduced, and the distillation purification step is performed. It becomes extremely complicated. Furthermore, in the method of using a tertiary alcohol such as a tertiary butanol as a solvent, the melting point of the alcohol rises and becomes a solid state at room temperature, so that the operability is significantly deteriorated. There was a problem to be done.
【０００４】[0004]
【解決しようとする課題】本発明は、従来法における問
題点を解決すべくなされたもので、その目的は工業的に
有利に実施することのできる３−アミノプロピオニトリ
ルの製造法を提供することにある。さらに具体的には、
蒸留分離しにくい副生物の生成を完全に抑制し、反応に
用いるアンモニアモル比を低減し、また、反応の操作性
を損なうことなく、効率の良い３−アミノプピオニトリ
ルの製造法を提供することにある。DISCLOSURE OF THE INVENTION The present invention has been made to solve the problems in the conventional method, and the object thereof is to provide a method for producing 3-aminopropionitrile which can be industrially advantageously carried out. Especially. More specifically,
The present invention provides a method for efficiently producing 3-aminopupionitrile that completely suppresses the production of by-products that are difficult to separate by distillation, reduces the molar ratio of ammonia used in the reaction, and does not impair the operability of the reaction. Especially.
【０００５】[0005]
【課題を解決するための手段】本発明は、アクリロニト
リルとアンモニアとを反応させ、３−アミノプロピオニ
トリルを製造する方法において、溶媒として第二級アル
コール類を用いることを特徴とする３−アミノプロピオ
ニトリルの製造法に関する。The present invention is a method for producing 3-aminopropionitrile by reacting acrylonitrile with ammonia, wherein a secondary alcohol is used as a solvent. The present invention relates to a method for producing propionitrile.
【０００６】以下に本発明の方法を詳細に説明する。本
発明の方法では、溶媒として、２−プロパノール、２−
ブタノール、２−ペンタノール、３−ペンタノール、３
−メチル−２−ブタノール、２−ヘキサノール、３−ヘ
キサノール、２−メチル−３−ペンタノール、４−メチ
ル−２−ペンタノールおよび３，３−ジメチル−２−ブ
タノールなどの第二級アルコール類を使用する。また、
これらの第二級アルコール類は２種以上混合して用いる
こともできる。混合使用の際、混合比は任意に定めるこ
とができる。The method of the present invention will be described in detail below. In the method of the present invention, 2-propanol, 2-
Butanol, 2-pentanol, 3-pentanol, 3
-Methyl-2-butanol, 2-hexanol, 3-hexanol, 2-methyl-3-pentanol, 4-methyl-2-pentanol and 3,3-dimethyl-2-butanol use. Also,
Two or more of these secondary alcohols can be mixed and used. When mixed and used, the mixing ratio can be arbitrarily determined.
【０００７】本発明の方法におけるアルコール溶媒の使
用量は、重量比でアクリロニトリル１に対して０．５か
ら２０倍量、好ましくは１から１０倍量の範囲で実施す
るのがよい。The amount of the alcohol solvent used in the method of the present invention is 0.5 to 20 times, preferably 1 to 10 times, the amount of acrylonitrile by weight.
【０００８】本反応で用いるアンモニアは、如何なる形
態のものでも使用可能であるが、通常は液体アンモニ
ア、アンモニア水、アンモニアガスまたはアンモニアの
アルコール溶液などが用いられる。アンモニアの使用量
は、アクリロニトリル１モルに対しアンモニア１から２
０倍モル量、好ましくは２から１０倍モル量の範囲で実
施するのがよい。The ammonia used in this reaction may be in any form, but liquid ammonia, aqueous ammonia, ammonia gas or an alcohol solution of ammonia is usually used. The amount of ammonia used is 1 to 2 for 1 mol of acrylonitrile.
It may be carried out in a molar amount of 0 times, preferably 2 to 10 times.
【０００９】本反応は、反応温度が４０℃から２００
℃、好ましくは７０℃から１５０℃の範囲で実施するの
がよい。In this reaction, the reaction temperature is from 40 ° C to 200 ° C.
C., preferably 70.degree. C. to 150.degree. C.
【００１０】本反応における反応時間は、１８０分以
内、好ましくは０．１分から６０分の範囲で実施するの
がよい。The reaction time in this reaction is 180 minutes or less, preferably 0.1 to 60 minutes.
【００１１】本発明の方法は、回分式又は連続式いずれ
の方法により実施することができる。The method of the present invention can be carried out by either a batch method or a continuous method.
【００１２】本発明の方法によれば、３−アルコキシプ
ロピオニトリルなど蒸留分離しにくい副生物の生成を抑
え、アンモニアモル比を低減し、効率よく３−アミノプ
ロピオニトリルを製造することができる。 また、本発
明の方法で得られる３−アミノプロピオニトリルは、ア
ルコキシプロピオニトリルなどの副生物が混入しないた
め蒸留によって簡単に単離精製でき、有機合成の原料に
用いられるばかりでなく、反応後、反応液をそのまま未
精製でこれらの用途に用いることも可能である。According to the method of the present invention, it is possible to suppress the production of by-products such as 3-alkoxypropionitrile which are difficult to separate by distillation, reduce the molar ratio of ammonia, and efficiently produce 3-aminopropionitrile. . Further, 3-aminopropionitrile obtained by the method of the present invention can be easily isolated and purified by distillation because it does not contain by-products such as alkoxypropionitrile, and can be used not only as a raw material for organic synthesis but also in the reaction. After that, the reaction solution can be directly used for these purposes without being purified.
【００１３】[0013]
【実施例】以下、実施例により本発明の構成および効果
をさらに具体的に説明するが、本発明はこれらの実施例
に何ら限定されるものではない。EXAMPLES The constitution and effects of the present invention will be described more specifically below with reference to examples, but the present invention is not limited to these examples.
【００１４】実施例１ ２００ｍｌステンレス製オートクレーブにアクリロニト
リル１０ｇおよび２−プロパノール４８ｇを投入し、オ
ートクレーブを密閉する。冷却下オートクレーブ内を窒
素ガスで置換する。オートクレーブ内を真空ポンプを用
いて減圧した後、液体アンモニア２４ｇを注入する。加
熱撹拌を開始し、１２０℃まで１０分間で加熱昇温す
る。１２０℃に達した後、ただちに冷却し、４０℃まで
冷却し過剰のアンモニアを排出する。オートクレーブを
開放し、反応液をガスクロマトグラフィーで分析したと
ころ、アクリロニトリルの転化率１００％で、３−アミ
ノプロピオニトリルの収率は７５％、副生するビスシア
ノエチルアミンの収率は１８％であった。Example 1 10 g of acrylonitrile and 48 g of 2-propanol are put into a 200 ml stainless steel autoclave, and the autoclave is closed. The inside of the autoclave under cooling is replaced with nitrogen gas. After depressurizing the inside of the autoclave using a vacuum pump, 24 g of liquid ammonia is injected. Start heating and stirring, and heat up to 120 ° C. in 10 minutes to raise temperature. Immediately after reaching 120 ° C, the mixture is cooled to 40 ° C and excess ammonia is discharged. The autoclave was opened, and the reaction mixture was analyzed by gas chromatography to find that the conversion of acrylonitrile was 100%, the yield of 3-aminopropionitrile was 75%, and the yield of biscyanoethylamine as a byproduct was 18%. there were.
【００１５】実施例２〜７ 表１に示した溶媒および反応条件を用いて、実施例１と
同様の方法でアクリロニトリルとアンモニアとの反応を
行なった。Examples 2 to 7 Using the solvents and reaction conditions shown in Table 1, acrylonitrile and ammonia were reacted in the same manner as in Example 1.
【００１６】比較例１〜３ 溶媒としてメタノール、エタノールまたは第３級ブタノ
ールを用いたこと以外は、実施例１と同様な方法でアク
リロニトリルとアンモニアとの反応を行なった。Comparative Examples 1 to 3 Acrylonitrile was reacted with ammonia in the same manner as in Example 1 except that methanol, ethanol or tertiary butanol was used as the solvent.
【００１７】比較例４ 溶媒を使用しないこと以外は、実施例１と同様の方法で
アクリロニトリルとアンモニアとの反応を行なった。Comparative Example 4 Acrylonitrile was reacted with ammonia in the same manner as in Example 1 except that no solvent was used.
【００１８】上述の実施例および比較例における反応結
果をまとめて表１に示す。The reaction results in the above-mentioned Examples and Comparative Examples are summarized in Table 1.
【００１９】[0019]
【表１】 [Table 1]
【００２０】[0020]
【発明の効果】本発明の方法によれば、蒸留分離しにく
いアルコキシプロピオニトリル類は副生せず、アンモニ
アの使用量を低減でき、効率よく３−アミノプロピオニ
トリルを得ることができる。また本発明は次のような利
点も有する。 （１）蒸留分離しにくい副生物が混入しないため精製が
容易である。 （２）蒸留分離しにくい副生物が混入しないため、反応
液をそのまま次の合成反応に使用できる。 （３）蒸留分離しにくい副生物が生成しないため、３−
アミノプロピオニトリルの収率が向上する。 （４）溶媒の融点が低く、操作性が良い。According to the method of the present invention, alkoxypropionitriles, which are difficult to separate by distillation, are not by-produced, the amount of ammonia used can be reduced, and 3-aminopropionitrile can be efficiently obtained. The present invention also has the following advantages. (1) Purification is easy because by-products that are difficult to separate by distillation are not mixed. (2) The reaction solution can be used as it is for the next synthesis reaction, because byproducts that are difficult to separate by distillation are not mixed. (3) Since by-products that are difficult to separate by distillation are not generated, 3-
The yield of aminopropionitrile is improved. (4) The melting point of the solvent is low and the operability is good.
Claims (1)
させ、３−アミノプロピオニトリルを製造する方法にお
いて、溶媒として第二級アルコールを用いることを特徴
とする３−アミノプロピオニトリルの製造法。1. A method for producing 3-aminopropionitrile, wherein a secondary alcohol is used as a solvent in the method for producing 3-aminopropionitrile by reacting acrylonitrile and ammonia.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19094693A JP3288145B2 (en) | 1993-07-05 | 1993-07-05 | Method for producing 3-aminopropionitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19094693A JP3288145B2 (en) | 1993-07-05 | 1993-07-05 | Method for producing 3-aminopropionitrile |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0717935A true JPH0717935A (en) | 1995-01-20 |
| JP3288145B2 JP3288145B2 (en) | 2002-06-04 |
Family
ID=16266312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19094693A Expired - Lifetime JP3288145B2 (en) | 1993-07-05 | 1993-07-05 | Method for producing 3-aminopropionitrile |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3288145B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009507897A (en) * | 2005-09-15 | 2009-02-26 | ビーエーエスエフ ソシエタス・ヨーロピア | Process for producing β-aminopropionic acid derivative |
| CN102827031A (en) * | 2012-08-31 | 2012-12-19 | 江苏兄弟维生素有限公司 | Beta-aminopropionitrile consecutive reaction process |
| JP2017095455A (en) * | 2015-11-26 | 2017-06-01 | 南亜塑膠工業股▲ふん▼有限公司 | Method for preparing n,n'-bis(2-cyanoethyl)-1,2-ethylenediamine |
| CN107473986A (en) * | 2017-08-07 | 2017-12-15 | 杭州鑫富科技有限公司 | A kind of β aminopropionitriles recovery method |
| CN115677532A (en) * | 2022-11-15 | 2023-02-03 | 万华化学集团股份有限公司 | Method for efficiently preparing beta-aminopropionitrile from acrylonitrile |
-
1993
- 1993-07-05 JP JP19094693A patent/JP3288145B2/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009507897A (en) * | 2005-09-15 | 2009-02-26 | ビーエーエスエフ ソシエタス・ヨーロピア | Process for producing β-aminopropionic acid derivative |
| CN102827031A (en) * | 2012-08-31 | 2012-12-19 | 江苏兄弟维生素有限公司 | Beta-aminopropionitrile consecutive reaction process |
| CN102827031B (en) * | 2012-08-31 | 2014-07-16 | 江苏兄弟维生素有限公司 | Beta-aminopropionitrile consecutive reaction process |
| JP2017095455A (en) * | 2015-11-26 | 2017-06-01 | 南亜塑膠工業股▲ふん▼有限公司 | Method for preparing n,n'-bis(2-cyanoethyl)-1,2-ethylenediamine |
| CN107473986A (en) * | 2017-08-07 | 2017-12-15 | 杭州鑫富科技有限公司 | A kind of β aminopropionitriles recovery method |
| CN107473986B (en) * | 2017-08-07 | 2019-09-10 | 杭州鑫富科技有限公司 | A kind of β-aminopropionitrile recovery method |
| CN115677532A (en) * | 2022-11-15 | 2023-02-03 | 万华化学集团股份有限公司 | Method for efficiently preparing beta-aminopropionitrile from acrylonitrile |
| CN115677532B (en) * | 2022-11-15 | 2024-05-03 | 万华化学集团股份有限公司 | Method for efficiently preparing beta-aminopropionitrile from acrylonitrile |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3288145B2 (en) | 2002-06-04 |
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