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Method for synthesizing 2, 3, 4, 4'-tetrahydroxybenzophenone (THBP)

A technology of tetrahydroxybenzophenone and p-hydroxybenzonitrile, which is applied in the field of synthesizing 2,3,4,4'-tetrahydroxybenzophenone, can solve the problems of complicated post-treatment process, high reaction temperature and poor environment. Friendly and other issues, to achieve the effect of reducing the amount of catalyst used, high catalytic activity, and reducing pollution

Inactive Publication Date: 2012-08-22
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are some obvious shortcomings in the existing synthetic methods, including low yield, high reaction temperature, complex post-treatment process or the use of environmentally unfriendly reagents, etc.

Method used

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  • Method for synthesizing 2, 3, 4, 4'-tetrahydroxybenzophenone (THBP)
  • Method for synthesizing 2, 3, 4, 4'-tetrahydroxybenzophenone (THBP)
  • Method for synthesizing 2, 3, 4, 4'-tetrahydroxybenzophenone (THBP)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1) Put 31.5 g (ie 0.25 mol) of pyrogallic acid, 150 ml of anhydrous ether and 28.6 g (ie 0.24 mol) of p-hydroxybenzonitrile into the reactor, stir at room temperature, and wait until the solid is completely dissolved, Add ZnCl 2 13.6 g (that is, 0.1 mol ), and immediately pass through dry hydrogen chloride gas, stop passing through hydrogen chloride after 3 hours, react at room temperature for 24 hours, and then pass through hydrogen chloride for 2 hours. After that, 48 ml of 20 wt% hydrochloric acid aqueous solution and 100 ml of diethyl ether were added, and heated to reflux for 2 h. Naturally cooled to room temperature after the reaction, the organic layer was separated, the aqueous layer was extracted 3 times with ether (23 ml each time), and the organic layers were combined. The obtained organic layer material was washed 3 times with water, and the anhydrous MgSO 4 Dry, filter with suction, and concentrate under reduced pressure to obtain 60.05 g of crude 2,3,4...

Embodiment 2

[0020] Example 2: Put 31.5 g (0.25 mol) of pyrogallic acid, 150 ml of anhydrous ether and 26.8 g (0.22 mol) of p-hydroxybenzonitrile into the reactor, stir at room temperature, and add ZnCl 2 12.25 g (that is, 0.09 mol ) and immediately pass through dry hydrogen chloride gas, stop passing through hydrogen chloride after 3 hours, react at room temperature for 26 hours, and then pass through hydrogen chloride for 2 hours. After that, 54 ml of 20 wt% hydrochloric acid aqueous solution and 100 ml of diethyl ether were added, and heated to reflux for 2 h. Naturally cooled to room temperature after the reaction, the organic layer was separated, the aqueous layer was extracted 3 times with ether (26ml each time), and the organic layers were combined. The organic layer was washed 3 times with water, and then washed with anhydrous MgSO 4 Dry, filter with suction, and concentrate under reduced pressure to obtain 58.36 g of crude 2,3,4,4'-tetrahydroxybenzophenone.

Embodiment 3

[0022] (1) Put 63.0 g (0.50 mol) of pyrogallic acid, 300 ml of anhydrous ether and 50.4 g (0.42 mol) of p-hydroxybenzonitrile into the reactor, stir at room temperature, and add ZnCl after the solid is completely dissolved. 2 29.8g (that is, 0.22 mol), and immediately pass through dry hydrogen chloride gas, stop passing through hydrogen chloride after 3 hours, react at room temperature for 20 hours, and then pass through hydrogen chloride for 2 hours. After that, 110 ml of 20 wt% hydrochloric acid aqueous solution and 200 ml of diethyl ether were added, and heated to reflux for 2 h. Naturally cooled to room temperature after the reaction, the organic layer was separated, the aqueous layer was extracted 3 times with ether (52 ml each time), and the organic layers were combined. The organic layer was washed three times with water and then washed with anhydrous MgSO 4 After drying, suction filtration and concentration under reduced pressure, 110.63 g of crude 2,3,4,4'-tetrahyd...

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Abstract

The invention relates to a method for synthesizing 2, 3, 4, 4'-tetrahydroxybenzophenone (THBP). The method comprises the steps of using pyrogallic acid and p-hydroxybenzonitrile as raw materials, conducting Hoesch reaction in anhydrous ether under the existence of hydrogen chloride and Lewis acid ZnCl2, conducting extraction and concentration to obtain crude THBP and conducting activated carbon discoloration and recrystallization to obtain refined THBP, wherein the molar ratio of pyrogallic acid to p-hydroxybenzonitrile is 1 to (0.96-0.83) and the dosage of the catalyst ZnCl2 and the pyrogallic acid is 49.0-59.6g / mol. The method has the advantages that the reaction conditions are moderate, the process is simple and feasible, the energy consumption is low and the environmental pollution is reduced.

Description

technical field [0001] The invention relates to a process for synthesizing 2,3,4,4'-tetrahydroxybenzophenone. 2,3,4,4'-Tetrahydroxybenzophenone is mainly used as an intermediate in organic synthesis and as a photosensitive agent intermediate in the microelectronics industry. Background technique [0002] 2,3,4,4'-Tetrahydroxybenzophenone (hereinafter referred to as THBP) is an important organic synthesis intermediate, which can be used in photoresists, pharmaceutical intermediates, ultraviolet rays in the microelectronics integrated circuit industry Absorbents, resin stabilizers, dyes, etc., which are mainly used as photosensitive agent intermediates for UV positive photoresists in the microelectronics industry. The chip linewidth of this photoresist microfabrication can reach 0.3~0.8μm. At present, the relevant research on THBP in my country is still in its infancy, and there are only a few domestic manufacturers with small scale and very limited output. With the rapid d...

Claims

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Application Information

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IPC IPC(8): C07C49/83C07C45/45
Inventor 秦清徐浩张宗和黄嘉玲钱星仲崇茂
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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