【作者】 张炜；

【导师】 陈新志； 钱超；

【作者基本信息】 浙江大学 ， 化学工程， 2011， 硕士

【摘要】 间氨基苯酚作为重要的有机原料和医药中间体,广泛应用于石油化学工业、农药、医药、印染等行业。但是,工业上合成间氨基苯酚的工艺一般存在反应条件苛刻、三废多、成本高等问题。所以,探索一种条件温和、三废少、成本低的间氨基苯酚的合成工艺具有显著的现实意义。本文在综述间氨基苯酚的用途、市场状况、合成方法的基础上,提出了一种条件较温和、操作简单、成本较低的间苯二胺选择性重氮化合成间氨基苯酚的工艺路线。该方法以间苯二胺为起始反应物,经单氨基成盐、醋酐单乙酰化合成了间氨基乙酰苯胺盐酸盐,再经重氮化和重氮盐的水解反应合成间氨基苯酚。论文在分析相关单元反应的机理基础上,实验探索了多步反应的工艺条件：制备间氨基乙酰苯胺盐酸盐合成的最佳反应条件为：醋酐：间苯二胺=1.1：1,滴加30%的盐酸溶液,反应温度40℃,在此条件下收率最高为92.5%；间氨基乙酰苯胺盐酸盐重氮化的最佳反应条件：间氨基乙酰苯胺盐酸盐：亚硝酸钠：硫酸=1：1.1：3,在20%的硫酸介质中,反应温度-10℃,在此条件下合成的重氮盐经过水解反应后得到的间氨基苯酚收率最高,为70.5%,以间苯二胺计总收率为65.2%,纯度高达99.9%。更多还原

【Abstract】 As an important intermediate of medicine and organic material, m-aminophenol is widely used in the petrochemical industry, pesticide, medicine, printing and dyeing industry. Nevertheless, the synthesis processes of m-aminophenol have some disadvantages with harsh reaction condition and large discharge of waste, and high cost. Therefore, it is of significant practical significance to explore a synthesis process with mild condition, low discharge of waste and low cost.The use and market situation and many synthesis methods were summarized in this dissertation. A process route called selective diazotization of m-phenylenediamine was put forward, with mild condition, low discharge of waste and low cost. M-phenylenediamine was used as the regent. Firstly,3’-aminoacetanilide hydrochloride was prepared with the yield 92.5%, via salt formation of one amino of m-phenylenediamine and acetylation reaction of the other. And then m-aminophenol was prepared with the yield 70.5% via diazotization reaction and hydrolysis of diazonium salt.The optimum reaction conditions of synthesizing m-aminophenol via acetylation reaction, diazotization reaction and hydrolysis of diazonium salt were researched in the experiment. The optimum reaction conditions in the synthesis of 3’-aminoacetanilide hydrochloride are as following:The molar ratio of acetic anhydride and m-phenylenediamine is 1:1.1, the concentration of hydrochloride acid is 30%, and the temperature of the reaction is 40℃. In this step, 3’-aminoacetanilide hydrochloride is gained in the yield of 92.5%. The optimum reaction conditions of diazotization reaction are as following:the molar ratio of 3’-aminoacetanilide hydrochloride, sodium nitrite, and sulfuric acid is 1:1.1:3, and the diazotization reaction was carried out in 20% sulfuric acid at-10℃. The diazonium salt synthesized at this condition gave the highest yield (70.5%) of m-aminophenol in the following hydrolysis reaction, the total yield of the whole process is 65.2%, with the purity of 99.9%.更多还原