硝酸胍对邻甲基苯乙酮硝化的实验研究  

Experiment Study on the Nitration of o-Methyl-acetophenone via Guandine Nitrate

作　　者：张雄[1] 王莉[1] 

机构地区：[1]浙江外国语学院科学技术学院,浙江杭州310012

出　　处：《广州化工》2015年第18期63-65,共3页GuangZhou Chemical Industry

基　　金：浙江外国语学院高层次项目培育(090550022014);无机化学双语教学示范课程(080600042014)

摘　　要：2-甲基-5-硝基-苯乙酮和2-甲基-3-硝基-苯乙酮是重要有机合成中间体,采用经典的浓硝酸和浓硫酸硝化体系很难合成到它们。采用具有硝化与保护双重作用的硝酸胍作为硝化试剂,研究了邻甲基苯乙酮的硝化反应。合成了2-甲基-5-硝基-苯乙酮和2-甲基-3-硝基-苯乙酮。考察了反应时间、反应物料比、反应溶液酸度对产物收率和位置选择性的影响。优化后的反应条件为:反应温度为0℃,反应时间5 h,n(硝酸胍)∶n(邻甲基苯乙酮)=1.5∶1。以85%的硫酸有利于硝基化反应,优势形成2-甲基-5-硝基-苯乙酮。用氢核共振谱验证了产物的结构,采用高效液相色谱对产物的纯度进行了分析。2-Methyl-5-nitro-acetophenone and 2-methyl-3-nitro-acetophenone are important intermediates in organic synthesis. It is difficult to synthesize them using the classic nitration system based on concentrated nitric acid and concentrated sulfuric acid. The method was developed selecting guanidine nitrate as a nitrating agent which had double function of nitration and protection, the nitration of o-methyl-acetophenone was studied. 2-Methyl-5-nitro-acetophenone and 2-methyl-3-nitro-acetophenone were prepared. The effect of the reaction time, molar ratio of guanidine nitrate to o-methyl-acetophenone and the concentration of sulfuric acid to the yield and the position of reaction were studied. The optimal reaction conditions were as follows： reaction temperature was 0 ℃, reaction time was 5 h, molar ratio of guanidine nitrate to o-methyl-acetophenone was 1. 5 and the concentration of sulfuric acid was 85% sulfuric acid. 2-Methyl-5-nitro-acetophenone was the preferential nitration product. The product structure was identified by 1 H NMR. The purity of the product was analyzed by HPLC.

关 键 词：硝酸胍 硝化 邻甲基苯乙酮 硝化机理 

分 类 号：O625.6[理学—有机化学]