Method for preparing 4,6-diacetylresorcinol by acetylating resorcinol

A technology of diacetyl resorcinol and resorcinol acetylation is applied in the field of preparation of 4,6-diacetyl resorcinol, and can solve the problems of high cost, environmental pollution, difficult operation and the like, and achieves the The effect of low viscosity, reducing chemical pollution and improving reaction efficiency

Active Publication Date: 2014-04-09
CHONGQING INST OF GREEN & INTELLIGENT TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
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  • 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

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Embodiment 1

[0012] temperature 90℃ , MSA / AN / Resorcinol (molar ratio) = 2.2 / 2.2 / 1, acetylation of resorcinol to prepare 4,6-diacetyl resorcinol: Measure 7mL of methanesulfonic acid and 11mL of acetic anhydride in 100mL In the three-necked 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 filtered with suction 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 (Z...

Claims

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Application Information

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Patent Type & Authority Applications(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
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