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Heterocyclic azo compound, and synthetic method and applications thereof

The technology of a heterocyclic azo and a synthesis method, which is applied in the field of compound synthesis, can solve problems such as the discussion of the properties and uses of undyed dyes, and achieve the effects of high color intensity, bright color and high molar extinction coefficient.

Active Publication Date: 2019-07-09
SHENYANG RES INST OF CHEM IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the properties and uses of such dyes have not been further explored.

Method used

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  • Heterocyclic azo compound, and synthetic method and applications thereof
  • Heterocyclic azo compound, and synthetic method and applications thereof
  • Heterocyclic azo compound, and synthetic method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] (1) 43 grams (98%, 0.5mol) of 5-amino-1H-1,2,4-triazole, 36 grams (99%, 0.51mol) of sodium nitrite, 2,5-dimethylacetyl Dissolve 84 grams of aniline (99%, 0.51mol) in 600 grams of water, add 110 grams of 20% hydrochloric acid dropwise at 0°C under nitrogen protection, after the addition is complete, heat up to 85°C for two hours, add sodium chloride for salting out , and filtered to obtain a monoazo intermediate.

[0034] (2) Dissolve the above-mentioned monoazo intermediate product in 500 grams of water, 200 grams of 20% hydrochloric acid, add dropwise 30% aqueous sodium nitrite solution at 0° C. under stirring, and place the diazotization reaction liquid in the potassium iodide starch test paper, The test paper turns blue, and the blue color does not disappear after stirring for three minutes, which is the end of the reaction. Add 74 grams of 2-naphthol (99%, 0.51mol), 40 grams of sodium bicarbonate, and 50 grams of toluene into the reactor, slowly add the above-menti...

Embodiment 2

[0038] (1) 72 grams (98%, 0.5mol) of 5-amino-1H-1,2,4-triazole-3-carboxylic acid methyl ester, 36 grams (99%, 0.51mol) of sodium nitrite, 2, 84 grams of 5-dimethylacetanilide (99%, 0.51mol) was dissolved in 600 grams of water, and 110 grams of 20% hydrochloric acid was added dropwise at 0°C under nitrogen protection. After the addition was completed, the temperature was raised to 85°C for two hours. Sodium chloride was added for salting out, and the monoazo intermediate was obtained by filtration.

[0039] (2) Dissolve the above-mentioned monoazo intermediate in 500 grams of water and 200 grams of 20% hydrochloric acid, add dropwise 30% sodium nitrite aqueous solution at 5°C under stirring, and place the diazotization reaction liquid on potassium iodide starch test paper, test paper Turn blue, stir for three minutes and the blue color does not disappear, which is the end of the reaction. Add 74 grams of 2-naphthol (99%, 0.51mol), 40 grams of sodium bicarbonate, and 50 grams o...

Embodiment 3-8

[0043]

[0044]

[0045] The nuclear magnetic data of embodiment 3-8 gained compound is as follows:

[0046]

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PUM

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Abstract

The invention belongs to the field of compound synthesis, and more specifically relates to a heterocyclic azo compound, and a synthetic method and applications thereof. The structure of the heterocyclic azo compound is represented by formula I, wherein R1 is H, C1-C15 alkyl, C1-C15 alkyloxy, phenyl, C1-C15 alkyl phenyl or C1-C15 alkoxy phenyl; R2 is H, C1-C15 alkyl, C1-C15 alkyloxy, phenyl, C1-C15alkyl phenyl, C1-C15 alkoxy phenyl, cyano, nitro or COOX; R3 is H, C1-C15 alkyl or C1-C15 alkyloxy; R4 is H or C1-C15 alkyl; and X is C1-C15 alkyl. The heterocyclic azo compound can be taken as a novel heterocyclic azo dye, is bright in color, is wide in chromatogram, and is relatively high in chromophoric intensity, and can be used for oil product dyeing calibration as a novel labeling compound.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a heterocyclic azo compound and its synthesis method and application. Background technique [0002] Triazole azo dyes are a very important class of azo compounds. These dyes have the advantages of non-carcinogenicity, non-toxicity, bright colors and wide chromatograms. They are widely used in dyeing cotton, wool and polyamide fibers. At present, the research work on benzene series and naphthalene series azo dyes is emphasized at home and abroad, and there is very little research work on heterocyclic compounds. Li Dejiang et al. Eight kinds of triazole azo dyes were synthesized by coupling azole-3-carboxylic acid with H acid, phenols and amines, and their structures were characterized. However, the performance and application of such dyes have not been further explored. Therefore, it is of practical significance to research and develop such compounds and to expand t...

Claims

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Application Information

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IPC IPC(8): C07D249/14G01N1/30
CPCC07D249/14G01N1/30G01N2001/302
Inventor 马瑛邢颖李文骁丛麟权王永华朱红卫
Owner SHENYANG RES INST OF CHEM IND