1-propylene oxygen basis-4-hydroxyanthraquinone-9, 10-diketone and method of preparing the same and application thereof

A technology of polytetrafluoroethylene board and reclaimed water, which is applied to the preparation of quinones, chemical instruments and methods, and the preparation of organic compounds, etc. It can solve the problems that are difficult to meet, the water content cannot be monitored in real time, continuous, on-line, and the time-consuming detection limit of water content And other issues

Inactive Publication Date: 2009-12-30
ZHONGBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But these conventional methods have 1 method not only time-consuming and low detection limit when detecting water content; question

Method used

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  • 1-propylene oxygen basis-4-hydroxyanthraquinone-9, 10-diketone and method of preparing the same and application thereof
  • 1-propylene oxygen basis-4-hydroxyanthraquinone-9, 10-diketone and method of preparing the same and application thereof
  • 1-propylene oxygen basis-4-hydroxyanthraquinone-9, 10-diketone and method of preparing the same and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: A kind of 1-allyloxy-4-hydroxy anthraquinone-9,10-dione, its molecular structure and reaction are as follows,

[0025]

[0026] The synthesis steps are as follows,

[0027]Under magnetic stirring and nitrogen protection, 5.5 g of anhydrous potassium carbonate was added in batches to 9.6 g of 1,4-dihydroxyanthraquinone- 9, 10-diketone solution, after 15-30min, a thick muddy potassium salt is formed, then add 200ml of dried DMF solution, heat the mixture to 55-60°C for 30min, add 18ml of allyl bromide, and then heat the mixture to 65-70°C, react for 40 hours, cool to 5°C, acidify with 80ml of 1M hydrochloric acid, add 300ml of water, 300ml of dichloromethane and stir well, at this time the phases are separated, the aqueous layer is extracted three times with 300ml of dichloromethane, and the organic phases are combined for extraction , continuously wash with 400ml water, 400ml brine, add MgSO 4 Dried, filtered, evaporated solvent to obtain about 11g pro...

Embodiment 2

[0036] The synthetic steps of 1-allyloxy-4-hydroxyanthraquinone-9,10-dione are as follows,

[0037] The steps are: 5g of anhydrous potassium carbonate is added to 9g of 1,4-dihydroxyanthraquinone-9,10-dione solution dissolved in 150ml of dried N,N-dimethylformamide, and after 15min Slurry potassium salt, then add 150ml of dried DMF solution, heat the mixture to 55°C for 30min, add 15ml of allyl bromide, then heat the mixture to 65°C, react for 35h, cool to 5°C, acidify with hydrochloric acid, and Add water, stir the dichloromethane fully, at this time the phases are separated, the aqueous layer is extracted three times with dichloromethane, the combined organic phase is extracted, continuously washed with water and brine, and added MgSO 4 Dry, filter, and evaporate the solvent to obtain the product, which is purified by silica gel chromatography.

[0038] All the other are the same as embodiment 1

Embodiment 3

[0040] The synthetic steps of 1-allyloxy-4-hydroxyanthraquinone-9,10-dione are as follows,

[0041] The steps are: add 6g of anhydrous potassium carbonate to 10g of 1,4-dihydroxyanthraquinone-9,10-dione solution dissolved in 250ml of dried N,N-dimethylformamide, and form after 30min Slurry potassium salt, then add 250ml of dried DMF solution, heat the mixture to 60°C for 60min, add 25ml of allyl bromide, then heat the mixture to 70°C, react for 45h, cool to 5°C, acidify with hydrochloric acid, and Add water, stir the dichloromethane fully, at this time the phases are separated, the aqueous layer is extracted three times with dichloromethane, the combined organic phase is extracted, continuously washed with water and brine, and added MgSO 4 Dry, filter, and evaporate the solvent to obtain the product, which is purified by silica gel chromatography.

[0042] All the other are the same as embodiment 1

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Abstract

The invention relates to an anthraquinone compound, in particular to the 1- propylene oxygen group-4- hydroxyanthraquinone-9, 10- diketone and the preparation and the application. The molecular structure is shown as follows: the compound has stronger fluorescence quantum yield and good light stability. When the organic solvent contains little water, the fluorescence carrier molecule easily forms hydrogen bond compound with water so as to make the fluorescence intensity rise rapidly. The characteristics of the above fluorescence response produced by the anthraquinone derivatives in the organic solvent with water can be used to make fluorescent sensors and can realize the in-situ testing and real-time testing on the small quantities of water in organic solvent.

Description

technical field [0001] The invention relates to an anthraquinone compound, specifically a 1-allyloxy-4-hydroxyanthraquinone-9,10-dione and its preparation method and application. Background technique [0002] The determination of water content is very important in chemical industry, textile and other fields. For example, the control of water content in the production of organic solvents and chemical reagents is very necessary. In the prior art, methods such as constant weight, distillation, specific gravity measurement, and conductivity are used to measure water content, which may not give satisfactory results or take a lot of time. The Karl Fischer method is a commonly used method for determining water content, but it cannot monitor water content in real time, continuously and on-line. However, with the development of detection technology and the advancement of science and technology, especially today when computer automatic control systems are widely used, people have hig...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/76C07C50/20C07C46/00
Inventor 焦晨旭杨云峰胡国胜耿绍玮罗莹
Owner ZHONGBEI UNIV
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