JPS58113176A - Production of o-aminophenylacetic lactam - Google Patents
Production of o-aminophenylacetic lactamInfo
- Publication number
- JPS58113176A JPS58113176A JP20995181A JP20995181A JPS58113176A JP S58113176 A JPS58113176 A JP S58113176A JP 20995181 A JP20995181 A JP 20995181A JP 20995181 A JP20995181 A JP 20995181A JP S58113176 A JPS58113176 A JP S58113176A
- Authority
- JP
- Japan
- Prior art keywords
- lactam
- reaction
- acid
- aminophenylacetic
- production
- 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
- Other In-Based Heterocyclic Compounds (AREA)
Abstract
(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.
Description
【発明の詳細な説明】
本発明は、’Ｎ、Ｎ’−メチレンビスフェニルアセトア
ミドを加熱分解して０−アミンメチルフェニル酢酸ラク
タムを製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 0-amine methylphenylacetate lactam by thermally decomposing 'N,N'-methylenebisphenylacetamide.
０−アミンメチルフェニル酢酸ラクタムは加水分解する
ことにより容易に０−アミンメチルフェニル酢酸に変換
され、セファロスポリン系抗生物質の中間体として有用
である。O-amine methylphenylacetic acid lactam is easily converted into 0-amine methylphenylacetic acid by hydrolysis, and is useful as an intermediate for cephalosporin antibiotics.
本発明者は、メチルフェニルアセトアミドとバラホルム
アルデヒド又はＮ−ヒドロキシメチルフェニルアセトア
ミドをポリリン酸溶液中で、脱水してｏ−アミノメチル
フェニル酢酸ラクタムを得（１）
る方法を提案してきた。The present inventor has proposed a method (1) for obtaining o-aminomethylphenylacetate lactam by dehydrating methylphenylacetamide and paraformaldehyde or N-hydroxymethylphenylacetamide in a polyphosphoric acid solution.
しかしながら、従来の方法によると脱水反応が進行する
につれてポリリン酸溶液中に水分が包含されその作用が
低下し、さらに脱水反応により生成した水分が反応系中
に蓄積し、原料を加水分解するなどの欠点があった。However, according to the conventional method, as the dehydration reaction progresses, water is included in the polyphosphoric acid solution, reducing its effectiveness, and the water generated by the dehydration reaction accumulates in the reaction system, causing problems such as hydrolyzing the raw materials. There were drawbacks.
そこで１本発明者はこれらの点を改善することを種々検
討した結果１本発明に到達した。Therefore, the inventor of the present invention conducted various studies to improve these points, and as a result, he arrived at the present invention.
すなわち１本発明は、 Ｎ、Ｎ’−メチレンビスフェ
ニルアセトアミドを酸溶液中で加熱することによって、
０〜アミンメチルフエニル酢酸ラクタムを製造する方法
に関するものである。That is, 1 the present invention provides the following steps: by heating N,N'-methylenebisphenylacetamide in an acid solution,
The present invention relates to a method for producing 0-amine methylphenyl acetate lactam.
本発明の方法に使用する原料であるＮ、Ｎ’−メチレン
ビスフェニルアセトアミドは、２モルのメチすることが
できる。Ｎ、Ｎ’−メチレンビスフェニルアセトアミド
は粉末として、また反応に使用する酸溶解した状態でも
使用することができる。N,N'-methylenebisphenylacetamide, which is a raw material used in the method of the present invention, can be methylated in an amount of 2 moles. N,N'-methylenebisphenylacetamide can be used as a powder or in a state dissolved in the acid used in the reaction.
酸溶液として、ビロリン酸、ポリリン酸、スル（２）
ホン酸、ハロゲン化カルボン酸、ギ酸のように反応条件
において薬液を呈する化合物があげられる。Examples of the acid solution include compounds that exhibit a chemical solution under the reaction conditions, such as birophosphoric acid, polyphosphoric acid, sulf(2)phonic acid, halogenated carboxylic acid, and formic acid.
これらの酸溶液の使用預け、 Ｎ、Ｎ’−メチレンビ
スフェニルアセトアミドに対して１〜２０ｉｌｉｉ倍。The use of these acid solutions is 1 to 20 times higher than N,N'-methylenebisphenylacetamide.
好ましくは２〜１５重量倍である。こり、より使用量が
少ないと反応操作が困難であり、これより使用量が多い
と反応後の分離工程が複雑になる。Preferably it is 2 to 15 times the weight. On the other hand, if the amount used is smaller, the reaction operation will be difficult, and if the amount used is larger than this, the separation process after the reaction will be complicated.
反応温度は８０〜１’？’Ｏ℃、好寸しくは９０〜１５
０℃である。これより低いと反応速度が小さく、これよ
り高いとタール状高沸物の副生が多くなり目的生成物の
収率が低下する。The reaction temperature is 80~1'? 'O℃, preferably 90-15
It is 0°C. If it is lower than this, the reaction rate will be low, and if it is higher than this, the by-product of tar-like high-boiling substances will increase and the yield of the target product will decrease.
反応圧力は常圧、加圧のいず丸でもよい。丑だ反応時間
は１〜３０時間である。The reaction pressure may be normal pressure or pressurized. The reaction time is 1 to 30 hours.
本発明の方法による反応は下式によって進行すＮ、Ｎ’
−）チレンビスフェニルアセトアミドを加（３）
熱すると目的生成物の０−アミノメチルフェニル酢酸ラ
クタムとメチルフェニルアセトアミドを副生成物として
生成する。したがって、この両者を抽出、蒸留などの手
段により分離し、０−アミノメチルフェニル酢酸ラクタ
ムを取得する。一方のメチルフェニルアセＩ・アミドは
回収され、公知の方法により酸の存在下にＩｉ、Ｎ’−
メチレンビスフェニルアセトアミドを生成し１本発明の
方法の原料として再使用される。The reaction according to the method of the present invention proceeds according to the following formula: N, N'
-) Heating tyrene bisphenylacetamide (3) When heated, the desired product 0-aminomethylphenylacetate lactam and methylphenylacetamide are produced as by-products. Therefore, both are separated by means such as extraction and distillation to obtain 0-aminomethylphenylacetic acid lactam. One methylphenylacel amide was recovered and treated with Ii,N'- in the presence of acid by a known method.
Methylene bisphenylacetamide is produced and is reused as a raw material in the process of the present invention.
本発明の方法を実施することによって、 Ｎ、Ｎ’−
メチレンビスフェニルアセトアミドから冒収率でＯ−ア
ミノメチルフェニル酢酸ラクタムを取得することができ
る。By carrying out the method of the invention, N, N'-
O-aminomethylphenylacetate lactam can be obtained in poor yield from methylene bisphenylacetamide.
実施例１〜１１
第１表に示すような酸を、谷３０１１反応器に入れて約
９０℃に加熱、攪拌しながら、この中にＮ、 Ｎ’−メ
チレンビスフェニルアセトアミド２．８２１（１０ｍｍ
ｏｌ ） を粉末状で加えた。反応液の温度’１１３
５〜１４０℃に保ちながら７時間反応させた。（ただし
、実施例６だけは１５０″Ｃ，１時（４）
間反応させた）
反応液を冷却した後、液体クロマトグラフィーで分析し
、未反応のＮ、Ｎ’−メチレンビスフェニルアセトアミ
ド、生成した０−アミノメチルフェニル酢酸ラクタム、
メチルフェニルアセトアミドをそれぞれ定量した。結果
を第１表に示す。Examples 1 to 11 Acids as shown in Table 1 were placed in a Tani 3011 reactor, heated to about 90°C, and 2.821 g of N,N'-methylene bisphenylacetamide (10 mm
ol) was added in powder form. Temperature of reaction solution '113
The reaction was carried out for 7 hours while maintaining the temperature at 5 to 140°C. (However, only in Example 6, the reaction was carried out at 150"C for 1 hour (4).) After the reaction solution was cooled, it was analyzed by liquid chromatography to determine whether unreacted N,N'-methylenebisphenylacetamide was formed or not. 0-aminomethylphenylacetic acid lactam,
Methylphenylacetamide was quantified. The results are shown in Table 1.
なお１反応率、収率は次式によって計算した。Note that the reaction rate and yield were calculated using the following formula.
（５） 特許出願人 宇部興産株式会社(5) Patent applicant: Ube Industries Co., Ltd.
Claims (1)
中で、加熱することを特徴とする０〜アミンメチルフエ
ニル酢酸ラクタムの製造方法。1. A method for producing 0-amine methylphenylacetate lactam, which comprises heating N,N'-)tyrene bisphenylacetamide in an acid solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20995181A JPS58113176A (en) | 1981-12-28 | 1981-12-28 | Production of o-aminophenylacetic lactam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20995181A JPS58113176A (en) | 1981-12-28 | 1981-12-28 | Production of o-aminophenylacetic lactam |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58113176A true JPS58113176A (en) | 1983-07-05 |
| JPS6321668B2 JPS6321668B2 (en) | 1988-05-09 |
Family
ID=16581362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20995181A Granted JPS58113176A (en) | 1981-12-28 | 1981-12-28 | Production of o-aminophenylacetic lactam |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58113176A (en) |
-
1981
- 1981-12-28 JP JP20995181A patent/JPS58113176A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6321668B2 (en) | 1988-05-09 |
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