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

A technology of dimethoxyfluoran and heat-sensitive dyes, which is applied in the field of preparation of 3',6'-dimethoxyfluoran yellow heat-sensitive dyes, and can solve the problems of inability to discharge, high energy consumption and product yield. Low problems, to achieve the effect of improving yield, low reaction temperature, and improving reaction rate

Active Publication Date: 2014-10-01
沈阳感光化工研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This preparation method has the following disadvantages: 1. High temperature equipment is required, and energy consumption is large; 2. A large amount of oxidation and hinge impurities are generated due to the reaction at high temperature for a long time, and the product yield is extremely low; 3. Since the product is approximately solid at the end of the reaction, The material cannot be discharged, and the extraction method cannot be dissolved because of the hinge substance, and its shape is still a large piece, and the material cannot be discharged, so it cannot be mass-produced on the equipment

Method used

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

Examples

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Effect test

Embodiment 1

[0020] In a 500 ml three-necked flask, add 16.64 grams of fluorescein with a content of 90%, 2 grams of polyethylene glycol-400 and 150 ml of toluene, start stirring, and stir at room temperature for 0.5 hours; add 8 g of sodium hydroxide under stirring, Stir and disperse at room temperature for 1 hour; then heat up to 60°C, add 19.9g of dimethyl sulfate dropwise in 0.5 hours, and keep warm for 4.0 hours; add 70ml of water and continue to react at 60°C for 0.5 hours; stand still, Separate the solvent layer, concentrate under reduced pressure and reclaim toluene to dryness, add 50 milliliters of methanol to disperse, filter and dry 14 grams of crude product; the crude product is subjected to column separation, the column packing is chromatographic neutral alumina, and the mobile phase is acetone and The mixed solution of chloroform (1:5), the first color band material was collected as the product, concentrated, filtered, and dried to obtain 12.5 grams of white product, the total...

Embodiment 2

[0022] In a 500 ml three-necked flask, add 16.64 g of fluorescein with a content of 90%, 1 g of tetrabutylammonium bromide and 150 ml of ethylbenzene, start stirring, and stir at room temperature for 0.75 hours; add 11.2 g of potassium hydroxide under stirring, and Stir and disperse for 0.5 hours; then heat up to 85°C, add 22.7g of dimethyl sulfate dropwise in 1.0 hour, and keep warm for 3.0 hours; add 60 ml of water and react at 85°C for 0.5 hours, separate the solvent layer, reduce Concentrate under pressure and recover ethylbenzene to dryness, add 50 milliliters of methanol to disperse, filter and dry 13.9 grams of crude product; the crude product is subjected to column separation, the column packing is chromatographic neutral alumina, and the mobile phase is a mixture of acetone and chloroform ( 1:7), the first color band material was collected as the product, concentrated, filtered, and dried to obtain 12.6 grams of white product, the total yield was 77.6%, and the liquid ...

Embodiment 3

[0024] In a 500ml three-necked flask, add 16.64g of fluorescein with a content of 90%, 1g of tetrabutylammonium bromide and 150ml of methyl ethyl benzene, start stirring, and stir at room temperature for 1 hour; add 13.8 potassium carbonate while stirring, stir and disperse at room temperature 0.85 hours; then heat up to 90°C, add 20g of dimethyl sulfate dropwise in 0.75 hours, and keep warm for 3.5 hours; add 85ml of water and react at 90°C for 1 hour; separate the solvent layer, concentrate and recover under reduced pressure Ethylbenzene to dryness, add 50 milliliters of methanol to disperse, filter, dry thick product 14.1 grams; Thick product carries out column separation, and column packing is chromatographic neutral alumina, and mobile phase is the mixed solution of acetone and chloroform (1:9 ), collect the first color band material as the product, concentrate, filter and dry to obtain 12.9 grams of white product, the total yield is 79.4%, and the product liquid color con...

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Abstract

The invention relates to a preparation method of 3', 6'-dimethoxy fluorane yellow thermosensitive dye, which comprises the following steps of: (1) adding fluorescein, solvent and phase transfer catalyst (PTC) into a reaction vessel, and stirring and dispersing for 0.5-1h at the room temperature, wherein the weight ratio between the fluorescein and the PTC is 7.5-15: 1; (2) heating up to 60-100 DEG C, dripping dimethyl sulfate into the mixture for 0.5-1h, wherein the molar ratio between the dimethyl sulfate and the fluorescein is 3.5: 1-4: 1; after that, carrying out reaction for 3-5h at the temperature of 60-100 DEG C; (3) adding water into the mixture, and continuously reacting for 0.5-1h at the temperature of 60-100 DEG C; (4) separating an organic layer and concentrating to obtain crude product; and (5) separating the crude product by column separation to obtain the 3', 6'-dimethoxy fluorane yellow thermosensitive dye. The method is simple in technology and suitable for industrial mass production; and the prepared product is high in yield and purity, thus being widely applied to producing a medical computed tomography (CT) piece.

Description

technical field [0001] The invention relates to a thermosensitive dye, in particular to a preparation method of 3', 6'-dimethoxyfluorane yellow thermosensitive dye used in medical CT films. Background technique [0002] As we all know, the structure of 3',6'-dimethoxyfluorane yellow thermosensitive dye is: [0003] [0004] The known preparation method of the dye is as follows: 1 mole of m-methoxyphenol and 0.5 mole of phthalic anhydride are reacted at 180-190°C for 10 hours under the catalysis of anhydrous zinc chloride. After the reactant is basically solidified, the solid is taken out by cooling down. Grinding, concentration with solvent extraction, column separation to obtain the product. This preparation method has the following disadvantages: 1. High temperature equipment is required, and energy consumption is large; 2. A large amount of oxidation and hinge impurities are produced due to the reaction at high temperature for a long time, and the product yield is ext...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00
Inventor 杨宗义千昌富于锦亮张占国
Owner 沈阳感光化工研究院有限公司
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