A kind of synthetic method of fluoran compound and its catalyst

A synthesis method and compound technology, applied in the direction of organic chemistry, triarylmethane dyes, etc., can solve the problems of difficult separation of colors of products, limit the production scale of products, increase the burden of three wastes treatment, etc., achieve cheap raw materials, reduce the generation and production of tar The effect of process safety

Active Publication Date: 2018-03-20
JIANGSU AOLUNDA HIGH TECH IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic methods adopted in the above patents are roughly the same, and fluoran compounds can be prepared, but the main problem of this method is that the use of concentrated sulfuric acid causes a large amount of black tar substances to be produced in the reaction system, and the product is difficult to separate and has a darker color. Qualified product can be obtained after purification but the actual yield is low
In addition, concentrated sulfuric acid is used as a solvent in a large amount. After the reaction, the system produces a large amount of waste acid, which increases the burden of three wastes treatment, correspondingly increases the cost, and limits the scale of product production.

Method used

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  • A kind of synthetic method of fluoran compound and its catalyst
  • A kind of synthetic method of fluoran compound and its catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Add 240g toluene, 37.6g 98% 2-(2-hydroxyl-4-diethylaminobenzoyl)benzoic acid (self-made, the same below) and 0.18 g catalyst (preparation of catalyst, graphene oxide by mass ratio: Al 2 o 3 : CuO=0.1:10:0.025, first add 10g of alumina to 50ml of deionized water, stir at 80°C for 1h, and at the same time disperse 0.1g of graphene oxide and 0.025g of copper oxide in 50ml of deionized water by ultrasonic, and then dissolve the dispersion Add the above alumina system, continue to stir for 3 hours, centrifuge, dry the solid in an oven, grind it into powder, then put the solid powder in a muffle furnace and slowly heat up from room temperature to 300 ° C for 5 hours, and then lower it to room temperature. The solid powder is the catalyst mentioned above, sealed and stored for future use), stir evenly, keep the temperature at 25°C and add 27.3g 98% 2,3′-dimethyl-4-methoxydiphenylamine dropwise (self-made, the same below) , after dripping, the mixture was warmed up to reflux ...

Embodiment 2

[0018] Add 240g toluene, 37.6g 98% 2-(2-hydroxyl-4-diethylaminobenzoyl) benzoic acid and 0.18g catalyzer in the reactor with condensation water separator, agitator and thermometer (preparation of catalyst , by mass ratio of graphene oxide: Al 2 o 3 : ZnO=0.1:10:0.025, the preparation method is the same as in Example 1), stir evenly, keep the temperature at 25°C, add 27.3g 98% 2,3′-dimethyl-4-methoxydiphenylamine dropwise, dropwise Then heat the mixture to reflux temperature and react for about 5 hours. During the process, the generated water is separated. After the reaction is completed, the catalyst is recovered by filtration while it is hot (applied after being washed with a solvent). The obtained organic phase is added to the flask together with 180g of 25% sodium hydroxide aqueous solution. Then fully stirred and refluxed for 1 h, separated the upper organic phase, washed the organic phase with hot water, concentrated and recovered the solvent, and recrystallized the resi...

Embodiment 3

[0020] Add 240g toluene, 37.6g 98% 2-(2-hydroxyl-4-diethylaminobenzoyl) benzoic acid and 0.18g catalyzer in the reactor with condensation water separator, agitator and thermometer (preparation of catalyst , by mass ratio of graphene oxide: Al 2 o 3 : Fe 2 o 3 =0.1:10:0.025, the preparation method is the same as in Example 1), stir evenly, keep the temperature at 25°C, add 27.3g98% 2,3′-dimethyl-4-methoxydiphenylamine dropwise, and mix the mixture Raise the temperature to reflux temperature and react for about 5 hours. During the process, remove the generated water. After the reaction is over, filter and recover the catalyst while it is hot (after washing with solvent, apply mechanically). The obtained organic phase is added to the flask together with 180g of 25% sodium hydroxide aqueous solution, and then fully stirred Reflux for 1 h, separate the upper organic phase, wash the organic phase with hot water, concentrate and recover the solvent, and recrystallize the residue w...

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Abstract

The invention relates to a synthesis method and a catalyst for fluorane compounds. The synthesis method comprises the step that under the action of the catalyst, a compound with a structure I and a compound with a structure II are subjected to refluxing in methylbenzene, and a product is obtained; the catalyst comprises components of oxidation graphite, aluminum oxide and transition metal oxide. The catalyst is prepared through steps as follows: aluminum oxide is added to deionized water and stirred for 1 h at the temperature of 80 DEG C, oxidation graphite and transition metal oxide are subjected to ultrasonic dispersion in another part of deionized water, a dispersion liquid is added to an aluminum oxide system and continues to be stirred for 3h, centrifugal separation is performed, solids are dried and ground into powder, the powder is placed in a muffle furnace, roasted for 5 h by slowly raising the temperature to 300 DEG C from the room temperature and cooled to the room temperature, and solid powder is obtained. With the adoption of the synthesis method and catalyst for the fluorane compounds, concentrated sulfuric acid is prevented from being used, produced tar is effectively reduced, the yield is increased, the reaction process is simplified, and large-scale production of products is facilitated.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a preparation method of fluoran compounds and a catalyst thereof. Background technique [0002] Fluorane compounds are widely used as color-forming agents in pressure-sensitive and heat-sensitive recording materials. They show good performance in background whiteness, storage stability, color rendering, color forming sensitivity and image color fastness of recording materials. performance. [0003] The synthesis of fluoran compounds is generally prepared by reacting ketoacids and diphenylamines under the action of concentrated sulfuric acid. For example, U.S. Patent No. 5,376,617 uses ketoacids and diphenylamines to react at room temperature for a certain period of time in the presence of concentrated sulfuric acid. After the end, pour it into the ice-water mixture, precipitate the solid, filter, and then reflux the obtained solid with toluene and alkaline water for...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/10C09B11/24
CPCC07D493/10C09B11/24
Inventor 万利兵陈律钮强
Owner JIANGSU AOLUNDA HIGH TECH IND
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