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Synthesis method of 9-anthracene carboxylic acid

A synthesis method, the technology of anthracene carboxylic acid, is applied in the field of synthesis of dye intermediates and electronic fluorescent materials, which can solve the problems of unavailable process catalysts, unavailable 9-anthracene boronic acid, and unsuitability for industrial production, and achieve stable product quality and easy operation. Simple, less by-product effect

Pending Publication Date: 2021-12-24
辽宁靖帆新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the catalyst used and 9-anthraceneboronic acid are not readily available
[0006] The literature [Transition Metal Chemistry, 2019, vol.44, #2, p.167-173] reported that 9-anthracene formaldehyde was used as raw material, catalyzed by a cobalt composite catalyst, illuminated by LED light for 150 hours, and the yield was 100%. Not easy to get, not suitable for industrial production

Method used

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  • Synthesis method of 9-anthracene carboxylic acid
  • Synthesis method of 9-anthracene carboxylic acid
  • Synthesis method of 9-anthracene carboxylic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0032] In the reaction flask, add 100g 9-anthracene formaldehyde, 1000g isopropanol, 50g 2-methyl-2-butene, add 113.5g sodium dihydrogen phosphate and 300g aqueous solution under stirring, add dropwise 68.6g sodium chlorite and 300g aqueous solution, temperature control 20-30°C. After the dropwise addition was completed, the reaction was stirred at room temperature for 2 h. After the reaction is completed, distill under reduced pressure, distill off the solvent, adjust the pH to 2-3 with 50g of concentrated hydrochloric acid, and precipitate a large amount of solids, add 1000g of ethyl acetate to stir to dissolve the solids, filter, rinse the filter cake with 200g of ethyl acetate, and separate the liquids , the organic phase was washed twice with 300 g×2 water, and the organic phase was evaporated to obtain 74.1 g of yellow solid, yield: 69.32%.

[0033] The prepared yellow solid was identified by proton nuclear magnetic spectrum, see figure 1 As shown, the results show tha...

Embodiment 2

[0037] In the reaction flask, add 100g 9-anthracene formaldehyde, 1500g isopropanol, 68g 2-methyl-2-butene, add 151g sodium dihydrogen phosphate and 300g aqueous solution under stirring, add dropwise 87g sodium chlorite and 300g aqueous solution , temperature control 20-30 ℃. After the dropwise addition, stir the reaction at room temperature for 2 hours, distill under reduced pressure, distill off the solvent, adjust the pH to 2-3 with 50 g of concentrated hydrochloric acid, and precipitate a large amount of solid, add 1000 g of ethyl acetate and stir to dissolve the solid, filter, and filter the cake with 200 g of ethyl acetate Rinse, separate liquid, wash the organic phase twice with 300 g×2 water, evaporate the organic phase to obtain 72 g of yellow solid, yield: 67.29%.

Embodiment 3

[0039] In the reaction flask, add 100g 9-anthracene formaldehyde, 1000g isopropanol, 34.02g 2-methyl-2-butene, add 151g sodium dihydrogen phosphate and 300g aqueous solution under stirring, add dropwise 39.47g sodium chlorite and 300g aqueous solution, temperature control 20-30°C. After the dropwise addition, stir the reaction at room temperature for 2 hours, distill under reduced pressure, distill off the solvent, adjust the pH to 2-3 with 50 g of concentrated hydrochloric acid, and precipitate a large amount of solid, add 1000 g of ethyl acetate and stir to dissolve the solid, filter, and filter the cake with 200 g of ethyl acetate Rinse, separate liquid, wash the organic phase twice with 300 g×2 water, evaporate the organic phase to obtain 75 g of yellow solid, yield: 69.65%.

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Abstract

The invention relates to the technical field of synthesis of dye intermediates and electronic fluorescent materials, and provides a novel synthesis method of 9-anthracene carboxylic acid. The synthesis method comprises the following steps of: taking 9-anthracene formaldehyde as a raw material, reacting under the action of an oxidizing agent, an auxiliary agent and a pH buffer agent, evaporating to remove a solvent after the reaction is completed, adjusting the pH to 1-5, extracting organic matters, and then evaporating to remove an organic phase, thereby obtaining 9-anthracene carboxylic acid. The problems of more by-products, low yield and the like in synthesis of 9-anthracene carboxylic acid in the prior art are solved. In synthesis, 9-anthracene formaldehyde is taken as a raw material, and reaction is performed under the action of an oxidizing agent, an auxiliary agent and a pH buffer agent. The prepared yellow solid is subjected to nuclear magnetic hydrogen spectrum identification and liquid chromatography detection, and results show that the structure of the prepared product is 9-anthracene carboxylic acid, and the purity can reach 99% or above, so that the synthesis method has the advantages of fewer by-products, easiness in purification, mild reaction conditions, simplicity in operation, stable product quality and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of synthesis of dye intermediates and electronic fluorescent materials, in particular to a synthesis method of 9-anthracenecarboxylic acid. Background technique [0002] 9-Anthracenecarboxylic acid is used as a dye intermediate and electronic fluorescent material, and its structural formula is as follows: [0003] [0004] The current method of synthesizing 9-anthracene formic acid has the following reports: [0005] GB2523811A reported that 9,10-dibromoanthracene was used as raw material, butyllithium was formed into lithium salt at -78°C, and then treated with dry ice to obtain 9-anthracenecarboxylic acid. This method is harsh and unsuitable for industrial production. The literature [Tetrahedron Letters, 2014, vol.55, #41, p.5671-5675] reported a method of synthesizing 9-anthracenecarboxylic acid by reacting 9-anthracenboronic acid and ethyl acetoacetate, with a yield of 87%. The method 9-anthracene b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C63/44C07C51/16C09K11/06
CPCC07C51/16C09K11/06C07C2603/24C09K2211/1011C07C63/44
Inventor 于景喜郑丽敏刘扬
Owner 辽宁靖帆新材料有限公司
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