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Preparation method of 6-hydroxy-2-naphthoic acid

A technology of naphthoic acid and sodium naphthoic acid, applied in the field of chemical technology, can solve the problems of poor conversion rate and selectivity, harsh reaction conditions and high equipment requirements, and achieve the effects of mild preparation conditions, low production cost and simple equipment requirements

Pending Publication Date: 2021-11-26
宿迁思睿屹新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There is the problem of the isomerization of 2-hydroxy-6-naphthoic acid in the above-mentioned disclosed technology, which leads to poor conversion rate and selectivity, more by-products, and the use of carbon monoxide is easy to cause personal injury, and the reaction conditions are harsh. more demanding

Method used

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  • Preparation method of 6-hydroxy-2-naphthoic acid
  • Preparation method of 6-hydroxy-2-naphthoic acid
  • Preparation method of 6-hydroxy-2-naphthoic acid

Examples

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Effect test

Embodiment 1

[0031] A preparation method of 6-hydroxyl-2-naphthoic acid, the steps are as follows:

[0032] Synthesis of S1, ethyl 6-hydroxy-2-naphthoate: 22.8g ethyl 6-isopropyl-2-naphthoate, 1.6g N-hydroxymethylphthalimide, 2.0g azo Diisoheptanonitrile and 150 mL of ethyl acetate were placed in a 500 mL single necked round bottom flask fitted with a balloon filled with oxygen. The mixture was stirred at 45°C for 10 hours. The reaction mixture was treated with dilute sulfuric acid solution at room temperature for 0.6 hours. The solvent was removed under reduced pressure to obtain a crude mixture, which was purified by silica gel column chromatography to obtain the product, 13.3 g of ethyl 6-hydroxy-2-naphthoate, with a yield of 66%;

[0033] S2. Synthesis of sodium 6-hydroxy-2-naphthoate: 20.2 g of ethyl 6-hydroxy-2-naphthoate and 50 mL of 0.2 g / mL sodium hydroxide aqueous solution were added to a single-necked round-bottomed flask, and stirred at 36 ° C for 10 hours to obtain Sodium 6...

Embodiment 2

[0036] A preparation method of 6-hydroxyl-2-naphthoic acid, the steps are as follows:

[0037] Synthesis of S1, ethyl 6-hydroxy-2-naphthoate: 22.8g ethyl 6-isopropyl-2-naphthoate, 1.6g N-hydroxymethylphthalimide, 2.0g azo Dimethyl diisobutyrate and 150 mL m-xylene were placed in a 500 mL single necked round bottom flask fitted with a balloon filled with oxygen. The mixture was stirred at 50°C for 10 hours. The reaction mixture was treated with dilute hydrochloric acid solution at room temperature for 0.8 hours. The solvent was removed under reduced pressure to obtain a crude mixture, which was purified by silica gel column chromatography to obtain the product, 16.1 g of ethyl 6-hydroxy-2-naphthoate, with a yield of 88%;

[0038] S2. Synthesis of sodium 6-hydroxy-2-naphthoate: 20.2 g of ethyl 6-hydroxy-2-naphthoate and 50 mL of 0.2 g / mL potassium hydroxide aqueous solution were added to a single-necked round-bottomed flask, stirred at 38 ° C for 10.5 hours, Obtain sodium 6-h...

Embodiment 3

[0041] A preparation method of 6-hydroxyl-2-naphthoic acid, the steps are as follows:

[0042] Synthesis of S1, ethyl 6-hydroxy-2-naphthoate: 22.8g ethyl 6-isopropyl-2-naphthoate, 1.6g N-hydroxymethylphthalimide, 2.0g azo Dimethyl diisobutyrate and 150 mL m-xylene were placed in a 500 mL single necked round bottom flask fitted with a balloon filled with oxygen. The mixture was stirred at 50°C for 10 hours. The reaction mixture was treated with dilute hydrochloric acid solution at room temperature for 0.9 hours. The solvent was removed under reduced pressure to obtain a crude mixture, which was purified by silica gel column chromatography to obtain the product, 16.1 g of ethyl 6-hydroxy-2-naphthoate, with a yield of 88%;

[0043] S2. Synthesis of sodium 6-hydroxy-2-naphthoate: 20.2 g of ethyl 6-hydroxy-2-naphthoate and 50 mL of 0.2 g / mL potassium carbonate aqueous solution were added to a single-necked round-bottomed flask, and stirred at 39 ° C for 11 hours to obtain 6 -Sod...

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Abstract

The invention provides a preparation method of 6-hydroxy-2-naphthoic acid, and particularly relates to the field of chemical processes. Herein, the ethyl 6-isopropyl-2-naphthoate is used as a raw material, isopropyl is hydroxylated through free radical reaction to prepare ethyl 6-hydroxy-2-naphthoate, and finally, the target product 6-hydroxy-2-naphthoic acid is prepared through hydrolysis and acidification. The method is mild in preparation condition, simple in equipment requirement and high in yield.

Description

technical field [0001] The invention belongs to the field of chemical technology, and in particular relates to a preparation method of 6-hydroxy-2-naphthoic acid. Background technique [0002] 6-Hydroxy-2-naphthoic acid is an important raw material for the preparation of liquid crystal polymers and heat-resistant resins. Due to its excellent performance, it is widely used in the preparation of substrates for 5G wireless communication equipment. But at present about the preparation of 6-hydroxyl-2-naphthoic acid, mainly focus on the following aspects: [0003] Among them, the patent numbers are US 1593816 and US 4345094, which disclose the preparation of 6-hydroxyl-2-naphthoic acid by Koble-Schimmit reaction. 6-hydroxy-2-naphthoic acid was prepared by using 2-naphthol potassium salt as a raw material to undergo carboxylation reaction at position 6 with carbon dioxide under high temperature and high pressure; [0004] The patent No. is JP 57-91955, which discloses the carbo...

Claims

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Application Information

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IPC IPC(8): C07C65/11C07C27/02C07C51/02C07C67/333C07C69/94
CPCC07C67/333C07C51/09C07C51/02C07C69/94C07C65/11
Inventor 柯友斌何珉刘雷张小雷
Owner 宿迁思睿屹新材料有限公司
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