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Method for preparing 4,6-diacetylresorcinol by acetylating resorcinol

A technology of diacetylresorcinol and resorcinol acetylation, which is applied in the field of preparation of 4,6-diacetylresorcinol, can solve the problems of high cost, difficult operation, environmental pollution, etc., and achieve Low viscosity, improved reaction efficiency, and reduced chemical pollution

Active Publication Date: 2015-07-15
CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Aiming at the current problems of serious environmental pollution, high cost and difficult operation in the preparation of 4,6-diacetyl resorcinol by acetylation of resorcinol, the present invention proposes an efficient, simple, environmentally friendly and low-cost method Method for preparing 4,6-diacetylresorcinol by acetylation of resorcinol

Method used

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  • Method for preparing 4,6-diacetylresorcinol by acetylating resorcinol
  • Method for preparing 4,6-diacetylresorcinol by acetylating resorcinol

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Embodiment 1

[0012] Under the conditions of temperature 90°C, MSA / AN / Resorcinol (molar ratio) = 2.2 / 2.2 / 1, acetylation of resorcinol to prepare 4,6-diacetyl resorcinol: measure 7mL of methanesulfonic acid, acetic anhydride Put 11mL in a 100mL three-neck flask, add 5.5g resorcinol into it, stir to dissolve, then raise the temperature to 90°C, take samples for HPLC every half hour, observe the reaction, after the reaction is completed, cool to room temperature, add water 15mL and methanol 10mL, heated to 80°C and stirred for half an hour, cooled to room temperature in the air, and suction filtered to obtain 4,6-diacetylresorcinol with a conversion rate of 77.8%.

Embodiment 2

[0014] Temperature 110°C, MSA / AN / Resorcinol (molar ratio) = 2.2 / 2.2 / 1, acetylation of resorcinol to prepare 4,6-diacetylresorcinol: Measure 7mL of methanesulfonic acid and 11mL of acetic anhydride in In a 100mL three-neck flask, under stirring conditions, add 5.5g resorcinol into it, stir to dissolve, raise the temperature to 110°C, take samples for HPLC every half hour, observe the reaction, after the reaction is completed, cool to room temperature, add water 15mL and methanol 10mL, heated to 80°C and stirred for half an hour, cooled to room temperature in the air, and suction filtered to obtain 4,6-diacetylresorcinol with a conversion rate of 84.6%.

Embodiment 3

[0016] Temperature 130°C, MSA / AN / Resorcinol (molar ratio) = 2.2 / 2.2 / 1, acetylation of resorcinol to prepare 4,6-diacetylresorcinol: Measure 7mL of methanesulfonic acid and 11mL of acetic anhydride in In a 100mL three-neck flask, under stirring conditions, add 5.5g resorcinol into it, stir to dissolve, raise the temperature to 130°C, take samples for HPLC every half hour, observe the reaction, after the reaction is completed, cool to room temperature, add water 15mL and 10mL of methanol, heated to 80°C and stirred for half an hour, cooled to room temperature in air, and suction filtered to obtain 4,6-diacetylresorcinol with a conversion rate of 90.5%.

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Abstract

The invention discloses a method for preparing 4,6-diacetylresorcinol by acetylating resorcinol under the action of methanesulfonic acid. The method mainly comprises the following step: by using methanesulfonic acid as a catalyst and acetic anhydride or acetic acid as an acylation reagent, reacting at 90-150 DEG C to convert resorcinol into the 4,6-diacetylresorcinol, wherein the methanesulfonic acid / acetic anhydride or acetic acid / resorcinol mole ratio is (0.5-5) / (1-5) / 1. Compared with the prior art, the method disclosed by the invention reduces the dependence on precursor chemicals, is more efficient, convenient and environment-friendly, and has the advantage of low cost.

Description

technical field [0001] The present invention relates to the preparation of 4,6-diacetyl resorcinol, mainly relates to the method of efficiently preparing 4,6-diacetyl resorcinol by using resorcinol under environment-friendly conditions, belonging to organic chemistry The field of synthetic technology. Background technique [0002] Friedel-Crafts acylation (FC) is widely used in the fields of medicine and chemical synthesis. It is the synthesis of 4,6-diaminoresorcinol (4,6-diaminoresorcinol, Abbreviation DAR) is the main method of intermediate 4,6-diacetylresorcinol. DAR is the key monomer for the synthesis of high-performance fiber poly-p-phenylenebenzobisoxazole (PBO). The purity of DAR monomer directly affects the quality of PBO polymer and final PBO fiber. The resorcinol acetylation and oximation method uses resorcinol as a raw material, through the process of diacetylation, oximation, Beckmann rearrangement, and rehydrolysis at the 4 and 6 positions, see figure 1 (Zh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/825C07C45/46
CPCC07C45/455C07C49/825
Inventor 陈凤贵徐愿坚高镱萌
Owner CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI