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

doi:10.13218/j.cnki.csdc.2014.09.115

日用化学工业 ›› 2014, Vol. 44 ›› Issue (9): 512-516.doi: 10.13218/j.cnki.csdc.2014.09.115

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

曾育才, 刘小玲, 李岚

嘉应学院化学与环境学院,广东梅州 514015

收稿日期:2014-04-16 出版日期:2014-09-22 发布日期:2019-04-08
作者简介:曾育才(1961-),男,副教授,学士,电话:13823838401,E-mail:mzzyc@jyu.edu.cn。
基金资助:
梅州市科技局与嘉应学院自然科研基金资助项目(2012KJZ03)

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

ZENG Yu-cai, LIU Xiao-ling, LI Lan

College of Chemistry and Environment,Jiaying College,Meizhou,Guangdong 514015,China

Received:2014-04-16 Online:2014-09-22 Published:2019-04-08

摘要/Abstract

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。

关键词: 6-苯偶氮香豆素-3-甲酸乙酯, 催化合成, 光谱性能

Abstract: 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 K₂CO₃ 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 1:2; dosage of K₂CO₃ 0.05 mmol and reaction time 15 min.Structure of the product was characterized by FTIR, ¹HNMR and ¹³CNMR.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.

Key words: 6-phenylazo-coumarin-3-ethyl formate, catalytic synthesis, spectroscopic property

中图分类号:

TQ655

曾育才, 刘小玲, 李岚. 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[J]. 日用化学工业, 2014, 44(9): 512-516.

ZENG Yu-cai, LIU Xiao-ling, LI Lan. Synthesis and spectroscopic property of 6-phenylazo-coumarin- 3-ethyl formate catalyzed by potassium carbonate[J]. China Surfactant Detergent & Cosmetics, 2014, 44(9): 512-516.

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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

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