甲基橙合成方法机理的新探究  

A New Study on Synthesis Mechanism of Methyl Orange

作　　者：张民[1] 袁桂梅[1] 夏玥穜 郭巧霞[1] 俞欣[1] 

机构地区：[1]中国石油大学(北京)理学院,北京

出　　处：《材料化学前沿》2024年第2期114-120,共7页Advances in Material Chemistry

摘　　要：通过实验验证,提出了一种甲基橙合成的新机理:由于氨基苯磺酸芳环上磺酸基的吸电子效应和强酸性,在室温下即可进行重氮化反应;由于N,N-二甲基苯胺“-NR2”的空间效应、R基与氨基N杂化轨道的超共轭效应以及磺酸基的吸电子效应和强酸性,在酸性条件下,偶合反应不但可以正常进行并且反应选择性增强,即亲电偶合反应更多发生在N,N-二甲基苯胺的对位上,从而在室温及pH < 2的酸性条件下生成产率、纯度均高的甲基橙产品。A new mechanism for the synthesis of methyl orange is proposed through experimental verification. Due to the electron absorption and strong acidity of the sulfonic group on the aromatic ring of aminobenzenesulfonic acid, diazotization reaction could be carried out at room temperature. Because of the space effect of N-dimethylaniline “-NR2”, the superconjugation effect of R-group and amino N hybrid orbital, the electron absorption effect and strong acidity of sulfonic group, the coupling reaction not only can be carried out normally, but also can be selectively enhanced under acidic conditions. As a result, the electrophilic coupling reaction takes place more frequently in the para-position of N-dimethylaniline, resulting in higher yield and higher purity of methyl orange products at room temperature and pH < 2 acidity.

关 键 词：常温 重氮化 酸性偶合反应 

分 类 号：O62[理学—有机化学]