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A kind of preparation method of pyronine dye

A technology of pyronin and dyes, which is applied in the field of preparation of pyronin dyes, can solve the problems of restricting the preparation and price of pyronin dyes, secondary pollution of the environment, and complicated post-processing, so as to reduce production costs and reaction time , the effect of reducing the amount of acid

Active Publication Date: 2017-08-15
山东埃米森生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has more reaction steps, longer reaction time, more complicated post-treatment, and lower yield (less than 38%). In addition, a large amount of acid needs to be used in the reaction, which easily causes secondary pollution to the environment.
Above-mentioned these deficiencies restrict the preparation and the price of pyronin dyestuff

Method used

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  • A kind of preparation method of pyronine dye
  • A kind of preparation method of pyronine dye
  • A kind of preparation method of pyronine dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] This embodiment takes the synthetic method of pyronin B as an example:

[0023] Put 4-diethylamino salicylaldehyde 1g (5.17mmol) and 855mg (5.17mmol) 3-diethylaminophenol into a 50ml one-port bottle, add 10ml concentrated phosphoric acid as solvent, the mass concentration of concentrated phosphoric acid is 90%, heat React at 150°C, stop heating after 4 hours of reaction, cool to room temperature, pour the reaction system into 30ml of water, add NaOH solution to adjust the pH value of the solution to 7, then add ammonium hexafluorophosphate (10.34mmol), there is solid precipitation

[0024] out, filtered, washed three times with water, and vacuum dried to obtain 1.98 g of pyronin B solid, with a yield of 82%.

[0025] The reaction equation is as follows:

[0026]

[0027] The optimization of specific reaction conditions is shown in the table below:

[0028] Reaction time 2h 3h 4h 5h 6h Yield (150℃) 50％ 63％ 75％ 81％ 81.3％ Yield (160℃) 62...

Embodiment 2

[0030] This embodiment takes the synthetic method of pyronin Y as an example:

[0031] Put 4-dimethylaminosalicylaldehyde 500mg (3mmol) and 415mg (3mmol) 3-dimethylaminophenol into a 50ml single-necked bottle, add 5ml concentrated phosphoric acid as solvent, the mass concentration of concentrated phosphoric acid is 95%, heat React at 160°C, stop heating after 5 hours of reaction, cool to room temperature, pour the reaction system into 30ml of water, add NaOH solution to adjust the pH of the solution to 8, then add ammonium hexafluorophosphate (6mmol) to precipitate solids, filter and wash with water three times , and dried in vacuo to obtain 1.25 g of pyronin Y as a solid, with a yield of 81%.

[0032] The reaction equation is as follows:

[0033]

[0034] 1 H NMR (300MHz, DMSO) δ8.79(s, 1H), 7.89(d, J=8.9Hz, 2H), 7.22(d, J=8.1Hz, 2H), 6.89(s, 2H), 3.29(s ,9H).

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Abstract

The invention discloses a preparation method of a pyronin dye. The preparation method is characterized in that the pyronin dye is prepared from 4-di-R-aminosalicylaldehyde and 3-di-R-amino phenol through a heating reaction in a one-step manner with phosphoric acid as a reaction solvent. Cheap salicylaldehyde and amino phenol are adopted as initial raw materials, so the preparation method has an obvious advantage in cost; and the yield and the purity of the obtained pyronin dye are high, the total yield reaches 82%, and the pyronin dye has a good application prospect in increase of the economic benefits of relevant enterprises.

Description

technical field [0001] The invention belongs to the technical field of organic material synthesis, and in particular relates to a preparation method of pyronin dye. Background technique [0002] Pyronine is a class of dyes with a wide range of uses. As shown in the structural formula below, when the R group is a methyl group, it is the well-known pyronin Y dye. Together with methyl green, it forms the methyl green-pyronin stain (MGP), which is commonly used in cell staining in biology. Among them, pyronin Y can combine with RNA in the cytoplasm or nucleolus, thereby staining the cytoplasm and nucleoli in red or reddish purple. At present, the synthetic method of pyronin dye is mainly synthesized with reference to the US patent (US 2011 / 0300074 A1). The synthetic equation is as follows. The method includes 2 steps of reaction. body, and then the resulting intermediate is subjected to dehydration reaction under concentrated sulfuric acid, and finally hydrochloric acid and s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00
CPCC09B57/00
Inventor 周鑫李红芳吴学
Owner 山东埃米森生物科技有限公司