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Method for preparing 3,3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene and application thereof

A technology of dinaphthylaminoazo and diaminoazobenzene, which is applied in the field of bistriazene compounds, can solve the problems of unsatisfactory reagent sensitivity and achieve the effects of high sensitivity, simple preparation method and stable performance

Inactive Publication Date: 2012-02-22
SHANXI DATONG UNIV
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Problems solved by technology

[0005] The present invention provides a 3,3'-dihydroxy-4,4'-bis(1,1'-dinaphthylaminoazo ) Azobenzene and its preparation method and application

Method used

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  • Method for preparing 3,3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene and application thereof
  • Method for preparing 3,3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene and application thereof
  • Method for preparing 3,3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene and application thereof

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Embodiment 1

[0036] Example 1, a method for preparing 3,3′-dihydroxy-4,4′-bis(1,1′-dinaphthylaminoazo)azobenzene, comprising the following steps: as attached figure 1 to show

[0037] ① Acetylation of 2-hydroxy-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-hydroxyl -4-Nitroaniline 77 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 3h 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 94g of the product with a yield of 95%.

[0038] ② Reduction of 2-hydroxy-4-nitroacetanilide Add 400ml of distilled water into a 1000ml round bottom flask, heat to 65℃, then ad...

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Abstract

The invention relates to bis-triazene compound, in particular to a method for preparing 3, 3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene and application thereof. A molecular structural formula of the 3,3'-dihydroxy-4,4'-di(1,1'-dinaphthylamine azo group) azobenzene is shown as an illustration below. The method is characterized in that naphthylamine and 3,3'-dihydroxy-4,4'- dinaphthylamine azo group which have a fluorescent characteristic are combined together through a diazotization reaction and a coupling reaction, so that a conjugated system of the compound is increased to be a ditriazene reagent, and the fluorescent characteristic of the reagent is improved. The reagent is a fluorescent reagent which is high in sensitivity of detecting Ag (I) in an alkaline medium and good in selectivity. Therefore, the reagent is not only a good photometric analysis color reagent but also a fluorescent analysis reagent which is good in sensitivity and selectivity and low in detection limit, and can be used for detecting silver ions in the alkaline medium.

Description

[0001] technical field [0002] The invention relates to a bistriazene compound, specifically a preparation method of 3,3'-dihydroxy-4,4'-bis(1,1'-dinaphthylaminoazo)azobenzene and its preparation method application. Background technique [0003] Triazene contains -N=N-NH-functional group, 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. Chen. Soc. DationTrans[J], 12(1991): 3435). Triazene reagent 1-azobenzene-3-(5-bromocyano-2-pyridine) triazene (Shao Bo, Wang Zhimin. Spectrum Laboratory, 2005, 22 (6): 1200-1203), 2, 4-dibromo-6-carboxyphenyldiazoaminoazobenzene (Wang Lei, Sun Peipei. Rock and Mineral Test, 1992, 11 (4): 326-329) is an excellent choice for heavy metal ions such as silver, cadmium, mercury, and nickel. Chromogenic reagents, because of their high sensitivity and easy synth...

Claims

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Application Information

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IPC IPC(8): C07C245/08C09K11/06G01N21/64
Inventor 王尚芝刘慧君樊月琴关翠林
Owner SHANXI DATONG UNIV
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