MANUFACTURING METHOD OF β-SUBSTITUTED PROPIONIC ACID AMIDE AND N-SUBSTITUTED (METH)ACRYLAMIDE

• Main Authors: HIRATA AKIMICHI, FURUSHO HARUKA, MASUDA HIDEKI, AOKI KAZUSHIGE
• Format: Patent
• Language: English; Japanese
• Published: 12.10.2017
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

PROBLEM TO BE SOLVED: To provide a method for industrially manufacturing β-alkoxy propionic acid amide, β-amino propionic acid amide and N-substituted (meth)acryl amide using (meth)acrylic acid ester as starting material at high yield and high purity.SOLUTION: There is provided a method for obtaining N-substituted (meth)acryl amide represented by target compound formula (7) by conducting an amidation reaction with amine using β-substituted propionic acid ester represented by the formula (1) of a product of a Michael addition reaction of (meth)acrylic acid ester and alcohol or amine in presence of a metal complex as a catalyst to obtain β-substituted propionic acid amide represented by the formula (3) and conducting a thermal decomposition reaction of β-substituted propionic acid amide in presence of the metal complex as the catalyst to eliminate alcohol or amine. A-CH-C(R)H-C(=O)-OR(1), A-CH-C(R)H-C(=O)-N(R)R(3), CH=C(R)-C(=O)-N(R)R(7)SELECTED DRAWING: None 【課題】（メタ）アクリル酸エステルを出発物質とする、高収率で高純度のβ−アルコキシプロピオン酸アミド、β−アミノプロピオン酸アミド及びＮ−置換（メタ）アクリルアミドを工業的に製造する方法。【解決手段】（メタ）アクリル酸エステルとアルコ−ル又アミンのマイケル付加反応の生成物の式（１）で表すβ−置換プロピオン酸エステルを用いて、触媒として金属錯体の存在下、アミンとアミド化反応を行い、式（３）で表すβ−置換プロピオン酸アミドを取得。更に、β−置換プロピオン酸アミドの熱分解反応を触媒とし金属錯体の存在下で行い、アルコ−ル或いはアミンを脱離させ、目的化合物式（７）で表されるＮ−置換（メタ）アクリルアミドを取得する方法。Ａ−ＣＨ２−Ｃ（Ｒ１）Ｈ−Ｃ（＝Ｏ）−ＯＲ２・・・（１）、Ａ−ＣＨ２−Ｃ（Ｒ１）Ｈ−Ｃ（＝Ｏ）−Ｎ（Ｒ３）Ｒ４・・・（３）、ＣＨ２＝Ｃ（Ｒ１）−Ｃ（＝Ｏ）−Ｎ（Ｒ３）Ｒ４・・・（７）【選択図】なし