碳酸钾催化合成6-苯偶氮香豆素-3-甲酸乙酯及其光谱性能  

Synthesis and spectroscopic property of 6-phenylazo-coumarin-3-ethyl formate catalyzed by potassium carbonate

作　　者：曾育才[1] 刘小玲[1] 李岚[1] 

机构地区：[1]嘉应学院化学与环境学院,广东梅州514015

出　　处：《日用化学工业》2014年第9期512-516,共5页China Surfactant Detergent & Cosmetics

基　　金：梅州市科技局与嘉应学院自然科研基金资助项目(2012KJZ03)

摘　　要：以苯胺为原料,经重氮化和偶合反应制得5-苯偶氮水杨醛(1)。探讨了介质的pH对偶合反应的影响,结果显示当pH=9时,1产率高达95.7%。然后以1和丙二酸二乙酯为原料、K2CO3为催化剂在无溶剂条件下合成了6-苯偶氮香豆素-3-甲酸乙酯(2),同时探讨了催化剂用量、反应时间和反应物摩尔比对2产率的影响。结果表明,当1物质的量为5 mmol、1与丙二酸二乙酯的摩尔比为1∶2、K2CO3用量为0.05 mmol和反应时间为15 min时,2产率可达82.5%。最后通过FTIR,1HNMR和13CNMR对产物2进行了结构表征,并测试了其在不同溶剂中的紫外吸收光谱和荧光发射光谱。结果表明,随着溶剂极性的增大,化合物2表现为正溶剂化显色,且斯托克斯位移较大。5 -Phenylazo salicylaldehyde （1） was prepared by successive diazotization and coupling reaction, starting from aniline. Effect of pH of the reaction medium on product yield of coupling reaction was investigated. When pH = 9, the yield can achieve 95.7%. 6 - Phenylazo - coumarin - 3 - ethyl formate （2） was synthesized with 1 and diethyl malonate using KECO3 as catalyst under solvent -free condition. Effects of dosage of the catalyst, reaction time and mole ratio of the reactants on the yield were investigated. Results indicated that yield of 2 achieves 82.5 % under conditions as ： 5 mmol of 1 ; mole ratio of 1 to ethyl malonate l： 2; dosage of K2CO3 0.05 mmol and reaction time 15 min. Structure of the product was characterized by FTIR, ~HNMR and ~3CNMR. UV absorption spectra and fluorescence emission spectra of the product 2 in various solvents were tested and observed. Results showed that as increase of polarity of the solvent used, the product displays positive solvatochromism and Stokes shifts of the product becomes bigger.

关 键 词：6-苯偶氮香豆素-3-甲酸乙酯 催化合成 光谱性能 

分 类 号：TQ245.24[化学工程—有机化工]