关于有机合成的毕业

论文

目 录

第一章 前言 .......................................................................................................................................... 2 1.1 3，3＇，5，5＇-四甲基联苯胺的概述 ...................................................................................... 2 1.2 国内外有关3，3＇，5，5＇-四甲基联苯胺的研究进展 ........................................................... 4 1.3 选题意义 ....................................................................................................................................... 5 第二章 实验部分 .................................................................................................................................. 6 2.1仪器和试剂 .................................................................................................................................... 6 2.1.1实验仪器 ................................................................................................................................. 6 2.1.2实验试剂 ................................................................................................................................. 6 2.2 3，3＇，5，5＇-四甲基联苯胺的合成与研究 .......................................................................... 7 2.2.1合成原理 ................................................................................................................................. 7 2.2.2合成方法 ................................................................................................................................. 7 第三章 结果与讨论 ............................................................................................................................ 10 3.1 溴化反应 ..................................................................................................................................... 10 3.2 偶联反应 ..................................................................................................................................... 10 3.2.1 反应温度对偶联反应的影响 .............................................................................................. 11 3.2.2 原料配比对偶联反应的影响 .............................................................................................. 12 3.3 溴化产物的表征图谱 ................................................................................................................. 12 第四章 结论 ........................................................................................................................................ 13 参考文献 ................................................................................................................................................ 14 致 谢 .................................................................................................................. 错误！未定义书签。

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3,3',5,5'-四甲基联苯胺的合成研究

制药工程专业 **级 ***

摘要：3,3',5,5'-四甲基联苯胺是一种新型安全的色原试剂,与传统的色原试剂如联苯胺、邻联甲苯胺及邻苯二胺等相比较,具有检测灵敏度高、稳定性好等优点,而且使用安全,无致癌、致突变作用。目前3,3',5,5'-四甲基联苯胺已在逐步取代强致癌物联苯胺和其他致癌性的联苯胺衍生物,应用于临床化验、法医检验、刑事侦破及环境监测领域。尤其在临床生化检验方面, 3,3',5,5'-四甲基联苯胺作为过氧化酶的新底物,在酶免疫分析法(EIA)和酶联免疫吸附检验法(ELISA)中获得了广泛的应用。可以作为一种专用于人体神经组织酶标和免疫酶标的研究及血液检验的试剂。

本方法以2,6-二甲基苯胺为起始原料，经过成盐、溴化、水解及偶联反应合成了3,3',5,5'-四甲基联苯胺，4步反应总收率46.56%。产品经1HNMR表征。该方法具有操作简单、成本低等优点，适合工业化生产。

关键词：2,6－二甲基苯胺；溴化；偶联；3,3',5,5'－四甲基联苯胺

The Synthesis of 3,3',5,5'-Tetramethylbenzidine

HuangLiyan,Grade 2009,Pharmarcettical Engineering

Abstract: 3,3',5,5'- tetramethylbenzidine is a new kind of safe color reagent. With traditional chromogen reagents such as benzidine, adjacent tolidine and compared o-phenylendiamine etc, has the advantages of high detection sensitivity, good stability, and the use of safe, no carcinogenic and mutagenic effects. Currently 3,3',5,5'- tetramethyl benzidine has been gradually replaced by strong carcinogens benzidine and other carcinogenic benzidine derivatives, the application in the clinical laboratory, field of forensic examination, forensic and environmental monitoring. Especially in the aspects of clinical and biochemical examination, 3,3',5,5'- tetramethyl benzidine as new substrates of peroxidase, the enzyme immunoassay (EIA) and enzyme-linked immunosorbent test (ELISA) has gained wide application.

3,3',5,5'-Tetramethylbenzidine was synthesized by using 2 , 6-dimethyl aniline as the starting material via salting, bromination, hydrolysis and coupling. The total yield of four steps was 46. 56%. Structure of the product was confirmed by 1HNMR. This method has many advantages, such as easy operation and low cost, which can be feasible to large scale preparation.

Key words: 2 , 6-dimethyl aniline; bromination; coupling; 3,3',5,5'-Tetramethyl- benzidine

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第一章 前言

1.1 3,3',5,5'-四甲基联苯胺的概述

3,3',5,5'-四甲基联苯胺( TMB )属联苯胺类化合物。联苯胺类化合物的通式为:

3H2N456211'6'5'2'3'4'NH2

联苯胺类化合物具体可分两大类，一类是:双联苯的苯环上2,2'、3,3'、5,5'和6,6'位被－H、－R、－OR、－NH2、－SO3H 和－Cl等基团取代的化合物( 其中R为甲基、丙基及丁基) ，如联苯胺、3,3'-二甲氧基联苯胺、3,3'－二甲基联苯胺、3,3'－二氨基联苯胺、2,2'－二磺酸基联苯胺、3,3',5,5'-四甲基联苯胺、3,3'－二氯联苯胺、3,3',5,5'－四氯联苯胺、3,3'－二丙氧基联苯胺和3,3'－二丁氧基联苯胺等; 另一类是: 4,4'位氨基N上的H被－R、－CH3CO、－C6H5和－CH2COOH 等基团取代的化合物，如N,N,N',N'－四甲基联苯胺、N,N,N',N'－四乙酰基联苯胺、N,N'－二乙酰基联苯胺、N,N'－二苯基联苯胺、N,N'－二羧甲基联苯胺和N,N,N',N'－四苯基联苯胺等。这些联苯胺类化合物的物化性质随着取代基数目及种类的不同，其在环境中以游离态、质子态、盐酸盐或硫酸盐以及钠盐等形式存在。

联苯胺类化合物广泛用于制造染料及有机颜料、化学分析及医用诊断的检测，其产量逐年增加，目前，在大气、河流、湖泊、地下水、

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