含吸电子基团的芳香醛的合成的研究-应用化学专业论文.docxVIP

摘要摘 摘要 摘 要 芳香醛类化合物是重要的有机中间体，广泛应用于医药、农药等领域。本文 概述了芳香醛化合物的种类及其合成方法，在通过对各种芳香醛化合物的合成工 艺进行比较之后，结合绿色化学的理念，在追求低成本、高效率、少污染的基础 上，开发了一种邻、对位含有吸电子基团的芳香醛的合成新工艺。 本文以邻、对位含有吸电子基团的甲苯取代物为起始原料，经与N，N．二甲 基甲酰胺缩二甲醛(DMFDMA)反应生成烯胺类化合物，烯胺类化合物再分别经 过氧化氢氧化和酸催化水解生成苯甲醛类化合物和苯乙醛类化合物。 通过对烯胺氧化的溶剂、温度、双氧水的用量、相转移催化剂等影响因素的 考察并优化，得到各种苯甲醛化合物(4．氯．2．硝基苯甲醛，2．氯．4．硝基苯甲醛， 4．硝基苯甲醛，2．硝基苯甲醛，4．氰基苯甲醛)的收率为83．4％，75．3％，71．3％，88．4％， 78．2％。通过对烯胺水解条件的优化，各苯乙醛类化合物(4．氯．2．硝基苯乙醛，2． 氯-4．硝基苯乙醛，4．硝基苯乙醛，2．硝基苯乙醛，4．氰基苯乙醛)的收率分别达到 95．7％，86．1％，92．1％，96．8％，84．1％。 改进后的工艺相对传统的合成方法具有反应条件温和，收率高，工艺操作简 便，污染少等优点，主要目标产物经1H-NMR核磁鉴定。 关键词：苯甲醛；苯乙醛；DMFDMA；合成；氧化；水解 III AbstractAbstract Abstract Abstract Aromatic aldehydes are very important organic intermediates，which are wildly used in medicine，pesticides and other areas．This article outlines the types and different synthesis methods of a variety of aromatic aldehydes．After comparing with each method，and based on the concept of green chemistry,combined with low cost，hi曲 efficiency and less pollution,we introduced all improved synthetic method of aromatic aldehydes which containe elctronwithdrawing groups in ortho or para position or bom of the aromatic ring． We used toluene substitutes which containe elctrowithdrawing groups in ortho or para position as a raw material，via reacting witll N，N—dimethylformamide dimethyl- acetaI(DMFDMA)to give styrylamine compounds，the styrylamine was oxidized under the presence of hydrogen peroxide and hydrolyzed under the presence of acid to give benzoic aldehydes and phenyl aldehydes respectively． By investigating and optimizing the influencing factors(such as the solvent，the temperature and the amount of hydrogen peroxide)on the enamine oxidation,the best yield of different benzoic aldehydes(2一nitro·4一chlorobenzaldehyde，2-chloro-4一nitro· benzaldehyde，4-Nitrobenzaldehyde，2-Nitrobenzaldehyde，4-Cyanobenzaldehyde)were 83．4％，75．3％，71．3％，85．3％，76．1％．By optimizing the hydrolysis conditions of enamines，the best yield of differentphenyl aldehydes(2一Nitro-4-chlorophenylacteal