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A kind of preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye

A technology of diethoxyfluoran and heat-sensitive dyes, which is applied in the field of heat-sensitive dyes, can solve the problems of many impurities, difficult discharge, and low yield, and achieve the effects of high purity, avoiding hydrolysis, and high yield

Active Publication Date: 2018-02-27
沈阳感光化工研究院有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the deficiencies in the prior art, the purpose of the present invention is to provide a high yield, simple post-treatment, suitable for large-scale production of 3,6-diethoxyfluorane yellow thermosensitive dye preparation method to solve The existing technology has problems such as difficult discharge, many impurities, and low yield.

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  • A kind of preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye
  • A kind of preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye
  • A kind of preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye

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preparation example Construction

[0023] In a specific embodiment, the preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye of the present invention comprises the following steps: (1) adding fluorescein and a solvent into a reaction vessel, stirring and dissolving at room temperature for 1-2 (2) After adding sodium hydroxide to react for 1 to 2 hours, add sodium carbonate; wherein, the molar ratio between sodium carbonate, sodium hydroxide and fluorescein is 2:2:1~4:2:1; (3) Heat to 40-90°C, add dibromoethane dropwise in 2-4 hours, the molar ratio of dibromoethane to fluorescein is 3:1-5:1, and react at this temperature after the addition is completed 6 to 16 hours; (4) add water to cool down to room temperature, stir and disperse for 8 to 10 hours, filter and dry to obtain the crude product; (5) recrystallize the crude product with a mixed solvent composed of ethyl acetate and dimethyl carbonate , to obtain 3,6-diethoxyfluorane yellow thermosensitive dye. in,

[0024] (1) The reaction formu...

Embodiment 1

[0031] Add 332g of fluorescein and 1000ml of solvent DMF into the reaction flask and stir to dissolve for 1 hour, then add 80g of sodium hydroxide to react for 1 hour, then add 210g of sodium carbonate, heat to 90°C, add 658g of dibromoethane dropwise, dropwise for 2 hours After completion, continue to keep warm at this temperature for 6 hours, add water, cool down to room temperature, stir and disperse for 8 hours, filter, rinse with a large amount of water, and dry to obtain a crude product. Add 351 grams of crude product, 530 ml of ethyl acetate and 530 ml of dimethyl carbonate and heat up to reflux. After all are dissolved, cool and precipitate, filter, and dry to obtain 310.4 g of white 3,6-diethoxyfluorane product with a content of 99.5 wt%. , yield 80%.

[0032] Such as figure 1 As shown, it can be seen that the NMR data are as follows:

[0033] Table 1: Analysis of 3,6-diethoxyfluorane NMR spectrum

[0034]

[0035] These data illustrate that the product structur...

Embodiment 2

[0037] Add 332g of fluorescein and 1000ml of solvent DMF into the reaction bottle, stir and dissolve for 1 hour, first add 80g of sodium hydroxide and react for 1 hour, then add 263g of sodium carbonate, heat to 80°C, add 658g of dibromoethane dropwise, and add dropwise for 2.5 hours After completion, continue to keep warm at this temperature for 8 hours, add water, cool down to room temperature, stir and disperse for 8.5 hours, filter, rinse with a large amount of water, and dry to obtain a crude product. Add 350 grams of crude product, 465 ml of ethyl acetate and 930 ml of dimethyl carbonate and heat up to reflux. After all are dissolved, cool and precipitate, filter and dry to obtain 309.6 g of white 3,6-diethoxyfluorane product with a content of 99.4 wt%. , yield 79.8%.

[0038] Such as figure 1 As shown, it can be seen that the NMR data are as follows:

[0039] Table 2: Analysis of 3,6-diethoxyfluorane NMR spectrum

[0040]

[0041] These data illustrate that the pr...

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Abstract

The invention relates to the field of thermosensitive dyes, in particular to a preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye. The method comprises: (1) adding fluorescein and a solvent into a reaction container, stirring and dissolving at room temperature for 1 to 2 hours; (2) adding sodium hydroxide and reacting for 1 to 2 hours, and then adding sodium carbonate; wherein, sodium carbonate, The molar ratio between sodium hydroxide and fluorescein is 2:2:1~4:2:1; (3) Heating to 40~90°C, adding dibromoethane dropwise in 2~4 hours, dibromoethane The molar ratio to fluorescein is 3:1~5:1, after the dropwise addition, react at this temperature for 6~16 hours; (4) Add water to cool down to room temperature, stir, disperse and precipitate for 8~10 hours, filter, dry, Obtain a crude product; (5) The crude product is recrystallized with a mixed solvent composed of ethyl acetate and dimethyl carbonate to obtain 3,6-diethoxyfluorane yellow thermosensitive dye. The method of the invention has simple process, is suitable for large-scale industrial production, and is widely used in the production of medical CT films.

Description

technical field [0001] The invention relates to the field of thermosensitive dyes, in particular to a preparation method of 3,6-diethoxyfluorane yellow thermosensitive dye. Background technique [0002] The structural formula of 3,6-diethoxyfluorane yellow thermosensitive dye is: [0003] [0004] The usual preparation method of the dye is as follows: m-ethoxyphenol and phthalic anhydride are reacted at high temperature under the catalysis of zinc chloride. After the reaction, the reactant is completely solidified, and it is difficult to discharge the material. A large amount of solvent is needed to obtain the product through column separation. The disadvantages of this reaction are: 1. The temperature is high and needs to reach 180° C., resulting in many side reactions, many impurities, and low yield. 2. The product is solidified and cannot be discharged, and it is difficult to post-process and cannot be produced. 3. The crude product has many impurities and needs to u...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09B57/00
Inventor 李昌德张秀岩刘勇宋昱刘景
Owner 沈阳感光化工研究院有限公司
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