Method for preparing 2-phenylamino-6-dibutylamino-3-methyl fluoran

A technology of dibutylamino and methylfluorane, applied in chemical instruments and methods, azo dyes, organic dyes, etc., can solve the problems of long-term low yield and achieve the effect of reducing consumption, cost and water

Active Publication Date: 2008-08-27
HEBEI JIANXIN CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Then stand to separate the toluene layer and concentrate, then add methanol to obtain 2-anilino-6-dibutylamino-3-methylfluoran α type, melting point 148-152 ° C. Then heat up in chlorobenzene and transform into high melting point The melting point of 2-phenylamino-6-dibutylamino-3-methylfluorane β type is 180-184°C. The above method has the disadvantage of long reaction process and low yield

Method used

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  • Method for preparing 2-phenylamino-6-dibutylamino-3-methyl fluoran
  • Method for preparing 2-phenylamino-6-dibutylamino-3-methyl fluoran
  • Method for preparing 2-phenylamino-6-dibutylamino-3-methyl fluoran

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Embodiment 1

[0015] Add 170g of 93% sulfuric acid into a 500ml reactor, slowly add 36.9g of 4-dibutylamino ketoacid (BBA) under stirring, finish adding in about 1 hour, wait until it is completely dissolved, then slowly add Add 21.3g of 2-methyl-4-methoxydiphenylamine (MMD) in 2-3 hours. The temperature of the whole process is controlled between 10-20°C, and the temperature is kept for 5-8 hours. Poured into a large amount of ice water, a large amount of solid matter was precipitated, filtered and washed to obtain a solid condensate. Add the condensate to a 1000ml reactor, add 50ml of toluene, 120ml of water, and then dropwise add 30% sodium hydroxide to keep the solution strongly alkaline at pH > 10, heat up and reflux for 2 to 4 hours, cool down to 20°C and crystallize and suction filter , washed and dried to obtain 42.5g of product, yield 79.6%, HPLC>99.5%, melting point: 183-183.5°C.

Embodiment 2

[0017] Add 170g of 96% sulfuric acid into a 500ml reactor, slowly add 36.9g of 4-dibutylamino ketoacid (BBA) under stirring, finish adding in about 1 hour, wait for it to completely dissolve, then slowly add Add 21.3g of 2-methyl-4-methoxydiphenylamine (MMD) in 2-3 hours. The temperature of the whole process is controlled between 10-20°C, and the temperature is kept for 5-8 hours. Poured into a large amount of ice water, a large amount of solid matter was precipitated, filtered and washed to obtain a solid condensate. Add the condensate to a 1000ml reactor, add 50ml of toluene, 120ml of water, and then dropwise add 30% sodium hydroxide to keep the solution strongly alkaline at pH > 10, heat up and reflux for 2 to 4 hours, cool down to 20°C and crystallize and suction filter , washed and dried to obtain 50.06g of product, yield 83.95%, HPLC>99.5%, melting point: 183.9-184.5°C.

Embodiment 3

[0019] Add 170g of 98% sulfuric acid into a 500ml reactor, slowly add 36.9g of 4-dibutylamino ketoacid (BBA) under stirring, finish adding in about 1 hour, wait until it is completely dissolved, then slowly add Add 21.3g of 2-methyl-4-methoxydiphenylamine (MMD) in 2-3 hours. The temperature of the whole process is controlled between 10-20°C, and the temperature is kept for 5-8 hours. Poured into a large amount of ice water, a large amount of solid matter was precipitated, filtered and washed to obtain a solid condensate. Add the condensate to a 1000ml reactor, add 50ml of toluene, 120ml of water, and then dropwise add 30% sodium hydroxide to keep the solution strongly alkaline at pH > 10, heat up and reflux for 2 to 4 hours, cool down to 20°C and crystallize and suction filter , washed, and dried to obtain 43.2 g of the product, with a yield of 81%, HPLC>99.5%, and melting point: 183.4-184.1°C.

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Abstract

The invention relates to a preparation method of 2-phenylamino-6-dibutylamino-3-methylfluorane, which comprises reacting 2-methyl-4-methoxy diphenylamine and 4-dibutylamino keto acid in 93-98% sulfate, controlling reaction temperature at 10-20DEG C and keeping the temperature for 2-20h, pouring the reaction solution into ice water to be solidified, filtering to obtain condensate, adding 30% sodium hydroxide, processing neutralization and cyclization in the presence of strong alkali while pH value is higher than 10, refluxing at 90-100DEG C, reducing temperature of 20DEG C, crystallizing and filtering to obtain 2-phenylamino-6-dibutylamino-3-methylfluorane. The invention can reduce the generation of side product and carbonizing matter in reaction, reduce reaction time, reduce cost and reduce the discharge of waste water in process.

Description

technical field [0001] The invention relates to a preparation method of thermosensitive dye 2-anilino-6-dibutylamino-3-methylfluorane (ODB-2). Background technique [0002] The thermosensitive dye 2-anilino-6-dibutylamino-3-methylfluoran represented by ODB-2 has been publicly reported in Japanese Patent No. 60-202155. The heat-sensitive dye 2-anilino-6-dibutylamino-3-methylfluoran is a very widely used coupler, especially the high melting point of this compound is 183-186°C, which makes its performance more stable, especially It has a good color forming effect when it is used as a color former or heat-sensitive material under pressure. [0003] The method disclosed in Japanese Patent No. 60-202155, which provides a low-melting α-type 2-phenylamino-6-dibutylamino-3-methylfluoran. Reaction steps: the reactants 2-methyl-4-methoxydiphenylamine (MMD) and 4-dibutylamino ketoacid (BBA) react under the condition of concentrated sulfuric acid, the reaction temperature is 0-5 ° C, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C09B57/00
Inventor 马增宝朱守琛朱秀全
Owner HEBEI JIANXIN CHEM IND CO LTD
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