JPH0827072A - Method for producing 2-methyl-1,2-propanediamine - Google Patents
Method for producing 2-methyl-1,2-propanediamineInfo
- Publication number
- JPH0827072A JPH0827072A JP6182905A JP18290594A JPH0827072A JP H0827072 A JPH0827072 A JP H0827072A JP 6182905 A JP6182905 A JP 6182905A JP 18290594 A JP18290594 A JP 18290594A JP H0827072 A JPH0827072 A JP H0827072A
- Authority
- JP
- Japan
- Prior art keywords
- propanediamine
- methyl
- hydrogenation
- methylpropionitrile
- acetylamino
- 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
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)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】この発明は２−アセチルアミノ−
２−メチルプロピオニトリルを水素添加した後、加水分
解を行って２−メチル−１，２−プロパンジアミンを製
造する方法に関する。２−メチル−１，２−プロパンジ
アミンはジヒドロイミダゾチアゾール環を形成するため
の原料であり、医薬品の解熱鎮痛消炎剤の合成中間体と
して利用される。This invention relates to 2-acetylamino-
The present invention relates to a method for producing 2-methyl-1,2-propanediamine by hydrogenating 2-methylpropionitrile and then performing hydrolysis. 2-Methyl-1,2-propanediamine is a raw material for forming a dihydroimidazothiazole ring, and is used as a synthetic intermediate for antipyretic and analgesic and antiphlogistic drugs.
【０００２】[0002]
【従来の技術】従来、２−アミノ−２−メチルプロピオ
ニトリルから２−メチル−１，２−プロパンジアミンを
得る方法としては、（１）２−アミノ−２−メチルプロ
ピオニトリルを直接水素添加する方法と、（２）アミノ
基をアセチル基で保護した後にニトリルを水素添加し更
に加水分解する方法が知られている。しかしながら、
（１）の方法では酸化白金、パラジウムという高価な触
媒を使用した時のみ可能であり、（２）の方法ではラネ
ー触媒により安全に水素添加することができるが、工程
数が増加する（特公昭４７−４４２０６号公報参照）。2. Description of the Related Art Conventionally, as a method for obtaining 2-methyl-1,2-propanediamine from 2-amino-2-methylpropionitrile, (1) 2-amino-2-methylpropionitrile is directly hydrogenated. A method of adding and a method of (2) protecting an amino group with an acetyl group and then hydrogenating a nitrile to further hydrolyze are known. However,
The method (1) is possible only when an expensive catalyst such as platinum oxide or palladium is used, and the method (2) can safely hydrogenate with a Raney catalyst, but the number of steps is increased (Japanese Patent Publication No. 47-44206).
【０００３】また、一般にニトリルの水素添加を行う場
合には、アンモニア存在下で反応が行われる。これは水
素添加中間体であるイミンと生成物のアミンが反応して
２級、３級アミンが副生するのを防ぐために使われる。
特公昭４７−４４２０６号公報では、上記（２）の方法
により２−メチル−１，２−プロパンジアミンを合成し
ているが、原料の約７倍モルという大過剰のアンモニア
存在下で水素添加を行っており、この為、アンモニアの
存在下で水素添加をし得る加圧装置が必要となり、また
加熱時にアンモニアの自圧により結果的に水素圧が高く
なるという問題があった。When hydrogenating a nitrile, the reaction is generally carried out in the presence of ammonia. This is used to prevent imine which is a hydrogenated intermediate and amine of the product from reacting with each other to form secondary and tertiary amines as by-products.
In Japanese Examined Patent Publication No. 47-44206, 2-methyl-1,2-propanediamine is synthesized by the method (2), but hydrogenation is carried out in the presence of a large excess of about 7 times the molar amount of the starting material. Therefore, there is a problem that a pressure device capable of hydrogenation in the presence of ammonia is required, and the hydrogen pressure eventually increases due to the self-pressure of ammonia during heating.
【０００４】[0004]
【発明が解決しようとする課題】したがって、本発明
は、上記問題点を解決するとともに、アンモニアの存在
しない系で副生物が生成することなく、２−メチル−
１，２−プロパンジアミンを高収率で得る方法を提供す
ることを目的とする。Therefore, the present invention solves the above-mentioned problems, and in addition to the formation of by-products in a system in which ammonia does not exist, 2-methyl-
It is an object to provide a method for obtaining 1,2-propanediamine in high yield.
【０００５】[0005]
【課題を解決するための手段】本発明者は、上記目的を
達成するために鋭意検討を重ねた結果、本発明に到達し
た。The inventor of the present invention has reached the present invention as a result of extensive studies to achieve the above object.
【０００６】すなわち、本発明は、２−アセチルアミノ
−２−メチルプロピオニトリルの水素添加反応を行い、
次いで加水分解することにより２−メチル−１，２−プ
ロパンジアミンを製造する方法において、アンモニアの
存在しない系でラネーニッケルを触媒とし、反応温度５
０〜１４０℃で水素添加反応を行い、次いで加水不分解
することを特徴とする２−メチル−１，２−プロパンジ
アミンの製造方法に関する。That is, the present invention performs a hydrogenation reaction of 2-acetylamino-2-methylpropionitrile,
Then, in the method for producing 2-methyl-1,2-propanediamine by hydrolysis, Raney nickel is used as a catalyst in a system without ammonia, and the reaction temperature is 5
The present invention relates to a method for producing 2-methyl-1,2-propanediamine, which comprises performing a hydrogenation reaction at 0 to 140 ° C. and then hydrolyzing and decomposing.
【０００７】以下本発明を詳細に説明する。The present invention will be described in detail below.
【０００８】まず本発明では、２−アセチルアミノ−２
−メチルプロピオニトリルを原料とする。水素添加（以
下単に水添という場合がある）触媒を用いて水添反応を
行う。First, in the present invention, 2-acetylamino-2
-Methylpropionitrile is used as a raw material. The hydrogenation reaction is carried out using a hydrogenation (hereinafter sometimes simply referred to as hydrogenation) catalyst.
【０００９】その際の水添触媒はラネーニッケルであ
り、その展開方法及び、第３種の添加物に制限はなく、
例えば、第３種の添加物としてモリブデンを添加したラ
ネーニッケルが使用される。The hydrogenation catalyst used in this case is Raney nickel, and there is no limitation on the method of its development and the additives of the third type.
For example, Raney nickel with molybdenum added as a third type additive is used.
【００１０】水添反応に用いられる反応溶媒としては、
アルコール、ジオキサン等の原料物質に対して溶解能が
あり、かつ上記水添条件で自ら水添されない溶媒が使用
可能で、好ましくはメタノール、エタノールである。そ
の際の原料濃度は０．２〜０．６ｇ／ｍｌ程度が好まし
く、より好ましくは０．４〜０．６ｇ／ｍｌの範囲であ
る。The reaction solvent used in the hydrogenation reaction is
It is possible to use a solvent which has a dissolving ability for a raw material such as alcohol and dioxane and which is not hydrogenated under the hydrogenation conditions described above, and preferred are methanol and ethanol. The raw material concentration at that time is preferably about 0.2 to 0.6 g / ml, and more preferably 0.4 to 0.6 g / ml.
【００１１】水添反応における反応温度は、５０〜１４
０℃、好ましくは１００〜１３０℃の範囲であり、また
水添反応における水素圧は、１０ｋｇ／ｃｍ2 程度でも
十分であり、好ましくは２０〜５０ｋｇ／ｃｍ2 であ
る。The reaction temperature in the hydrogenation reaction is 50 to 14
0 ° C., preferably in the range of 100 to 130 ° C., Hydrogen pressure in the hydrogenation reaction is sufficient in order 10 kg / cm 2, preferably from 20 to 50 kg / cm 2.
【００１２】本発明における水添反応によって得られる
生成物は、２，４，４−トリメチルイミダゾリンと２−
アセチルアミノ−２−メチルプロピルアミンの混合物で
ある。その生成比は約６：４である。正常に水添が行わ
れ、さらに環化反応が完全に行われれば、２，４，４−
トリメチルイミダゾリンだけが得られるが、本発明では
水素添加が終了した時点で反応を終了し次の加水分解を
行う。２，４，４−トリメチルイミダゾリンと２−アセ
チルアミノ−２−メチルプロピルアミンの両者ともに加
水分解によって目的化合物の２−メチル−１，２−プロ
パンジアミンに変換されるので、転化率が１００％とな
れば２，４，４−トリメチルイミダゾリンと２−アセチ
ルアミノ−２−メチルプロピルアミンの比に関係無く加
水分解工程に移ることが可能である。The product obtained by the hydrogenation reaction in the present invention is 2,4,4-trimethylimidazoline and 2-
It is a mixture of acetylamino-2-methylpropylamine. The production ratio is about 6: 4. If hydrogenation is carried out normally and the cyclization reaction is carried out completely, 2,4,4-
Only trimethylimidazoline can be obtained, but in the present invention, the reaction is terminated and the next hydrolysis is performed at the time when the hydrogenation is completed. Both 2,4,4-trimethylimidazoline and 2-acetylamino-2-methylpropylamine are converted to the target compound 2-methyl-1,2-propanediamine by hydrolysis, so that the conversion rate is 100%. Then, it is possible to proceed to the hydrolysis step regardless of the ratio of 2,4,4-trimethylimidazoline and 2-acetylamino-2-methylpropylamine.
【００１３】加水分解工程は、酸又はアルカリ加水分解
で行われ、好ましくはアルカリ加水分解で行なわれる。
使用されるアルカリとしては、苛性カリ水溶液又は苛性
ソーダ水溶液であるが、好ましくは苛性ソーダ水溶液で
あり、原料１ｍｏｌに対し濃度２５〜３０％の苛性ソー
ダ水溶液７００〜１０００ｇが適当である。The hydrolysis step is carried out by acid or alkali hydrolysis, preferably alkali hydrolysis.
The alkali used is an aqueous solution of caustic soda or an aqueous solution of caustic soda, preferably an aqueous solution of caustic soda, and 700 to 1000 g of an aqueous caustic soda solution having a concentration of 25 to 30% relative to 1 mol of the raw material is suitable.
【００１４】加水分解後処理時の抽出溶媒としては、ジ
エチルエーテル、ジイソプロピルエーテルなどが使用さ
れる。Diethyl ether, diisopropyl ether and the like are used as an extraction solvent at the time of post-hydrolysis treatment.
【００１５】[0015]
【実施例】以下に、実施例を挙げて本発明をさらに具体
的に説明する。EXAMPLES The present invention will be described more specifically below with reference to examples.
【００１６】参考例１ アセトンシアンヒドリン５６．５ｇに２５％アンモニア
水２５０ｍｌを添加した。１０分撹拌して１０℃程度の
発熱が収まった後、水浴を４０℃まで上昇させた。その
後反応温度を４０〜４５℃に保って３時間撹拌して反応
せしめた。１０℃まで冷却後、ジクロロメタン１００ｍ
ｌで４回抽出し、抽出液に無水硫酸ナトリウムを添加し
て乾燥した。その後無水硫酸ナトリウムを濾別して、ジ
クロロメタンを留去し、無色油状物の２−アミノ−２−
メチルプロピオニトリル４４．９ｇを得た。なお収量収
率は８０．４％、純度換算収率は６８％（ガスクロマト
グラフ面積百分率８４．２％）であった。Reference Example 1 250 ml of 25% aqueous ammonia was added to 56.5 g of acetone cyanohydrin. After stirring for 10 minutes and generation of heat of about 10 ° C. subsided, the temperature of the water bath was raised to 40 ° C. After that, the reaction temperature was kept at 40 to 45 ° C. and the reaction was carried out by stirring for 3 hours. After cooling to 10 ° C, dichloromethane 100m
It was extracted 4 times with 1 times and dried by adding anhydrous sodium sulfate to the extract. After that, anhydrous sodium sulfate was filtered off, and dichloromethane was distilled off to give 2-amino-2-
44.9 g of methylpropionitrile was obtained. The yield was 80.4% and the purity conversion yield was 68% (gas chromatograph area percentage 84.2%).
【００１７】参考例２ トルエン１１００ｍｌと無水酢酸２４８ｇを混合した溶
液を水浴で１４〜３４℃に保ちながら、この混合溶液
に、２−アミノ−２−メチルプロピオニトリル２４８ｇ
を４０分かけて滴下した。滴下途中から結晶が析出して
スラリー状態となった。滴下が終わってから３０℃で４
時間撹拌した。その後１０℃まで冷却後、濾過した。結
晶をトルエン１００ｍｌで４回洗浄した後、５０℃で減
圧乾燥し、２−アセチルアミノ−２−メチルプロピオニ
トリル２６９．９ｇを得た。なお収率は９０％であっ
た。Reference Example 2 While keeping a solution prepared by mixing 1100 ml of toluene and 248 g of acetic anhydride in a water bath at 14 to 34 ° C., 248 g of 2-amino-2-methylpropionitrile was added to this mixed solution.
Was added dropwise over 40 minutes. Crystals were precipitated during the dropping to form a slurry. 4 at 30 ℃ after dropping
Stirred for hours. Then, after cooling to 10 ° C., it was filtered. The crystals were washed 4 times with 100 ml of toluene and then dried under reduced pressure at 50 ° C. to obtain 269.9 g of 2-acetylamino-2-methylpropionitrile. The yield was 90%.
【００１８】実施例１ １００ｍｌオートクレーブに２−アセチルアミノ−２−
メチルプロピオニトリル２５．０ｇ（０．１９８モ
ル）、メタノール４２ｍｌ（原料濃度０．６ｇ／ｍｌメ
タノール）及び触媒としてラネーニッケル２．５ｇを仕
込み、１２００ｒｐｍの速度で撹拌しながら水素圧２０
〜５０ｋｇ／ｃｍ2 、温度１００℃で５時間反応させ
た。オートクレーブの温度が室温まで下ってから触媒を
反応液から濾別し、触媒はメタノール５０ｍｌで洗浄し
た後、洗浄液を反応液に加えた。反応液をエバポレータ
ーで溶媒を除去して、無色透明のオイル状物２７．３ｇ
を得た。得られたオイル状物は２，４，４−トリメチル
イミダゾリンと２−アセチルアミノ−２−メチルプロピ
ルアミンの混合物であった。Example 1 2-Acetylamino-2-in a 100 ml autoclave
25.0 g (0.198 mol) of methyl propionitrile, 42 ml of methanol (concentration of raw material 0.6 g / ml methanol) and 2.5 g of Raney nickel as a catalyst were charged, and hydrogen pressure was 20 while stirring at a speed of 1200 rpm.
The reaction was carried out at a temperature of 100 ° C for 5 hours at -50 kg / cm 2 . After the temperature of the autoclave had dropped to room temperature, the catalyst was filtered off from the reaction solution, the catalyst was washed with 50 ml of methanol, and then the washing solution was added to the reaction solution. After removing the solvent from the reaction solution with an evaporator, 27.3 g of a colorless transparent oily substance is obtained.
I got The obtained oily substance was a mixture of 2,4,4-trimethylimidazoline and 2-acetylamino-2-methylpropylamine.
【００１９】このようにして得られた混合物に２５％苛
性ソーダ水溶液１４０ｇを加え、撹拌しながら４時間還
流した。反応後３０℃まで冷却してから、苛性ソーダ２
５ｇを加え約２０分撹拌した。この溶液をジイソプロピ
ルエーテル１００ｍｌで３回抽出した。有機層を硫酸ナ
トリウムで乾燥した後、ジイソプロピルエーテルを蒸留
分離し、濃度５７％の２−メチル−１，２−プロパンジ
アミン２７．８ｇ（濃度換算収率８９％）を得た。この
溶液をさらに蒸留することにより、純度９９％の２−メ
チル−１，２−プロパンジアミン１３．２ｇを得た。な
お２−アセチルアミノ−２−メチルプロピオニトリルか
らの収率は７６％である。To the mixture thus obtained, 140 g of 25% aqueous sodium hydroxide solution was added, and the mixture was refluxed for 4 hours with stirring. After the reaction, cool to 30 ° C and then add caustic soda 2
5 g was added and stirred for about 20 minutes. This solution was extracted 3 times with 100 ml of diisopropyl ether. After the organic layer was dried over sodium sulfate, diisopropyl ether was separated by distillation to obtain 27.8 g of 2-methyl-1,2-propanediamine having a concentration of 57% (concentration conversion yield 89%). By further distilling this solution, 13.2 g of 2-methyl-1,2-propanediamine having a purity of 99% was obtained. The yield from 2-acetylamino-2-methylpropionitrile is 76%.
【００２０】実施例２ 水添反応における反応温度を１３０℃とし、実施例１と
同様にして水素添加および加水分解を行った結果、濃度
５０％の２−メチル−１，２−プロパンジアミン２８．
８ｇ（濃度換算収率８３％）を得た。この溶液を更に蒸
留することにより、純度９９％の２−メチル−１，２−
プロパンジアミン１２．１ｇを得た。なお２−アセチル
アミノ−２−メチルプロピオニトリルからの収率は６９
％である。Example 2 Hydrogenation and hydrolysis were carried out in the same manner as in Example 1 except that the reaction temperature in the hydrogenation reaction was 130 ° C., and as a result, the concentration of 2-methyl-1,2-propanediamine 28.
8 g (concentration conversion yield 83%) was obtained. By further distilling this solution, 99% pure 2-methyl-1,2-
12.1 g of propanediamine was obtained. The yield from 2-acetylamino-2-methylpropionitrile was 69.
%.
【００２１】実施例３ ２−アセチルアミノ−２−メチルプロピオニトリル２
５．０ｇ（０．１９８モル）に対してメタノール６３ｍ
ｌを使用し（原料濃度０．４ｇ／ｍｌメタノール）、実
施例１と同様にして水素添加および加水分解を行った結
果、濃度４６％の２−メチル−１，２−プロパンジアミ
ン３４．０ｇ（濃度換算収率８９％）を得た。この溶液
をさらに蒸留することにより純度９９％の２−メチル−
１，２−プロパンジアミン１３．０ｇを得た。なお２−
アセチルアミノ−２−メチルプロピオニトリルからの収
率は７５％である。Example 3 2-Acetylamino-2-methylpropionitrile 2
Methanol 63 m against 5.0 g (0.198 mol)
1 was used (raw material concentration 0.4 g / ml methanol), and hydrogenation and hydrolysis were carried out in the same manner as in Example 1, and as a result, 34.0 g (46% concentration of 2-methyl-1,2-propanediamine) was obtained. A concentration-converted yield of 89%) was obtained. This solution was further distilled to obtain 99% pure 2-methyl-
13.0 g of 1,2-propanediamine was obtained. 2-
The yield from acetylamino-2-methylpropionitrile is 75%.
【００２２】比較例１ 水添反応における反応濃度を１５０℃とし、実施例１と
同様にして水素添加および加水分解を行った結果、濃度
３４％の２−メチル−１，２−プロパンジアミン２８．
７ｇ（濃度換算収率５５％）を得た。この溶液をさらに
蒸留することにより、純度９９％の２−メチル−１，２
−プロパンジアミン８．１ｇを得た。なお２−アセチル
アミノ−２−メチルプロピオニトリルからの収率は４６
％である。Comparative Example 1 Hydrogenation and hydrolysis were carried out in the same manner as in Example 1 except that the reaction concentration in the hydrogenation reaction was 150 ° C., and as a result, concentration of 34% 2-methyl-1,2-propanediamine 28.
7 g (concentration conversion yield 55%) was obtained. By further distilling this solution, 99% pure 2-methyl-1,2
-8.1 g of propanediamine are obtained. The yield from 2-acetylamino-2-methylpropionitrile is 46.
%.
【００２３】[0023]
【発明の効果】本発明によれば、アンモニアの存在しな
い系であっても副生物が生成することなく、２−アセチ
ルアミノ−２−メチルプロピオニトリルの水素添加を行
うことで２−メチル−１，２−プロパンジアミンを高収
率で得ることが可能となり、工業的に実施する上で非常
に簡便でかつ有利である。INDUSTRIAL APPLICABILITY According to the present invention, 2-acetyl-amino-2-methylpropionitrile is hydrogenated by the hydrogenation of 2-acetylamino-2-methylpropionitrile without the formation of by-products even in the absence of ammonia. It is possible to obtain 1,2-propanediamine in a high yield, which is very simple and advantageous for industrial implementation.
Claims (1)
オニトリルの水素添加反応を行い、次いで加水分解する
ことにより２−メチル−１，２−プロパンジアミンを製
造する方法において、アンモニアの存在しない系で、ラ
ネーニッケルを触媒とし反応温度５０〜１４０℃で水素
添加反応を行い、次いで加水分解することを特徴とする
２−メチル−１，２−プロパンジアミンの製造方法。1. A method for producing 2-methyl-1,2-propanediamine by carrying out a hydrogenation reaction of 2-acetylamino-2-methylpropionitrile and then hydrolyzing the system, which is free from ammonia. A method for producing 2-methyl-1,2-propanediamine, which comprises subjecting Raney nickel as a catalyst to a hydrogenation reaction at a reaction temperature of 50 to 140 ° C., and then performing hydrolysis.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6182905A JPH0827072A (en) | 1994-07-12 | 1994-07-12 | Method for producing 2-methyl-1,2-propanediamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6182905A JPH0827072A (en) | 1994-07-12 | 1994-07-12 | Method for producing 2-methyl-1,2-propanediamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0827072A true JPH0827072A (en) | 1996-01-30 |
Family
ID=16126433
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6182905A Pending JPH0827072A (en) | 1994-07-12 | 1994-07-12 | Method for producing 2-methyl-1,2-propanediamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0827072A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005113512A1 (en) * | 2004-05-19 | 2005-12-01 | Ranbaxy Laboratories Limited | Process for the preparation of 1,2-diamines |
| EP2283833A2 (en) | 2004-02-25 | 2011-02-16 | La Jolla Pharmaceutical Co. | Amines and amides for the treatment of diseases |
| CN105585505A (en) * | 2015-12-25 | 2016-05-18 | 辽宁本源制药有限公司 | A new preparation method of anegliptin intermediate 1,2-diamino-2-methylpropane |
-
1994
- 1994-07-12 JP JP6182905A patent/JPH0827072A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2283833A2 (en) | 2004-02-25 | 2011-02-16 | La Jolla Pharmaceutical Co. | Amines and amides for the treatment of diseases |
| WO2005113512A1 (en) * | 2004-05-19 | 2005-12-01 | Ranbaxy Laboratories Limited | Process for the preparation of 1,2-diamines |
| CN105585505A (en) * | 2015-12-25 | 2016-05-18 | 辽宁本源制药有限公司 | A new preparation method of anegliptin intermediate 1,2-diamino-2-methylpropane |
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