3,3'-diethoxy-4,4'-di(8-hydroxy-5-quinoline ammonia azo)azobenzene and preparation method and application thereof
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A technology of quinoline aminoazo group and diaminoazobenzene is applied in the field of bistriazene compounds, and can solve the problems of unsatisfactory reagent sensitivity and the like, and achieve the effects of high sensitivity, stable performance and simple preparation method
Inactive Publication Date: 2012-07-04
SHANXI DATONG UNIV
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[0006] The present invention provides a 3,3'-diethoxy-4,4'-bis(8-hydroxy-5-quinoline) in order to solve the problem that the sensitivity of the reagents for detecting heavy metal zinc ions in the prior art is not ideal enough Preparation method and application of aminoazo)azobenzene
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Embodiment 1
[0042] Example 1, a preparation method of 3,3'-diethoxy-4,4'-bis(8-hydroxy-5-quinolineaminoazo)azobenzene, comprising the following steps: as attached figure 1 to show
[0043] ① Acetylation of 2-ethoxy-4-nitroaniline In a 250ml round bottom flask equipped with a reflux condenser and a dropping funnel, add 60ml of glacial acetic acid and 30ml of acetic anhydride (0.31 mol), and add 2 - Ethoxy-4-nitroaniline 91.0 g (0.5 mol). Then slowly heat to reflux, then slowly add 27.2ml (0.29 mol) of acetic anhydride to the above solution dropwise, continue to reflux for 2h after the dropwise addition, and naturally cool to room temperature after the reaction is completed, add 150ml of ice water, and dissolve in sodium hydroxide neutralize, filter with suction, wash with water, and dry under an infrared lamp to obtain 101 g of the product with a yield of 90%.
[0044] ② Reduction of 2-ethoxy-4-nitroacetanilide Add 400ml of distilled water to a 1000ml round bottom flask, heat to 60°C, t...
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Abstract
The invention relates to a di-triazene compound, in particular to a preparation method and an application of 3,3'-diethoxy-4,4'-di(8-hydroxy-5-quinoline ammonia azo)azobenzene, which is used for solving the problem of non-ideal sensitivity of a reagent for detecting heavy metal zinc ions existing in the prior art. The molecular structural formula of the 3,3'-diethoxy-4,4'-di(8-hydroxy-5-quinoline ammonia azo)azobenzene is shown in the specifications. The 3,3'-diethoxy-4,4'-di(8-hydroxy-5-quinoline ammonia azo)azobenzene is characterized in that: 5-amino-8-oxychinolin and 3,3'-diethoxy-4,4'-diamido-azobenzene with fluorescent characteristics are combined together to construct a di-triazene reagent with a larger conjugated system, so that the sensitivity and fluorescent characteristic of the reagent are enhanced. The 3,3'-diethoxy-4,4'-di(8-hydroxy-5-quinoline ammonia azo)azobenzene can be used for detecting zinc ions in an alkaline medium.
Description
[0001] technical field [0002] The invention relates to a bistriazene compound, specifically a method for preparing 3,3'-diethoxy-4,4'-bis(8-hydroxy-5-quinolineaminoazo)azobenzene and its application. Background technique [0003] Triazene contains -N=N-NH- functional groups. Due to P-π conjugation, =N-H has strong acidity. Under alkaline conditions, it is easy to coordinate with transition metal ions after deprotonation, which is very good Coordinating group (J. Barker, N. D. Cameron, M. Kilner, et al., J. Chem. Soc. DationTrans[J], 1991, 12: 3435). Triazene reagent 1-(2,6-dichloro-4-nitrobenzene)-3-(4-nitrobenzene)-triazene (Zhang Xinyan, Pan Jie, Yang Minghua, etc. China Environmental Monitoring [J], 2003, 19 (2): 41-43), 1-azobenzene-3-(5-bromo-2-pyridine) triazene (Gu Yongbing, Zhang Chunniu, Zheng Yunfa. Chemical analysis and measurement [J], 2005, 14 (1): 29-31) etc. are excellent chromogens for zinc ions. Because of their high sensitivity and easy synthesis, they...
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