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Preparation method of 3,5-dimethylphenol

A technology of dimethylphenol and dimethylphenol ester is applied in the field of preparation of 3,5-dimethylphenol, and achieves the effects of low cost of raw materials, mild reaction conditions and less three wastes

Active Publication Date: 2015-07-08
RONGCHENG QINGMU CHEM MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the technology of using this oxidation reaction characteristic to prepare 3,5-dimethylphenol is still blank

Method used

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  • Preparation method of 3,5-dimethylphenol

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Experimental program
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Effect test

Embodiment 1

[0024] (1) Synthesis of 3,5-dimethylacetophenone:

[0025] Add 1.0 mol of acetyl chloride dropwise to the mixture of aluminum trichloride and mixed xylene (2.0 mol of aluminum trichloride and 10.0 mol of xylene) under the condition of ice-water bath, control the dropping temperature not to exceed 15°C, and finish adding Afterwards, the temperature was raised to 100°C and stirred for 5 h. After the reaction, the reaction solution was poured into 1000 ml of ice water. The organic phase was separated, and washed with 0.5% dilute hydrochloric acid, saturated sodium carbonate solution, and water until neutral. After drying with anhydrous sodium sulfate, concentrate under reduced pressure, rectify the concentrate under reduced pressure, and collect the fraction at 94~98℃ / 5mmHg, which is the product 3,5-dimethylacetophenone (yield 89.2%), yellow liquid .

[0026] (2) Synthesis of 3,5-dimethylphenol ethyl ester:

[0027] Add 0.5mol of 3,5-dimethylacetophenone into 1000ml of dichlo...

Embodiment 2

[0031] (1) Synthesis of 3,5-dimethylacetophenone:

[0032]Add 1.0 mol of acetyl chloride dropwise to the mixture of aluminum trichloride and mixed xylene (1.0 mol of aluminum trichloride and 10.0 mol of xylene) in an ice-water bath, and control the dropping temperature not to exceed 15°C. Afterwards, the temperature was raised to 100° C. and stirred for 5 h. After the reaction, the reaction solution was poured into 1000 ml of ice water. The organic phase was separated, and washed with 0.5% dilute hydrochloric acid, saturated sodium carbonate solution, and water until neutral. After drying with anhydrous sodium sulfate, concentrate under reduced pressure, rectify the concentrate under reduced pressure, and collect the fraction at 94~98℃ / 5mmHg, which is the product 3,5-dimethylacetophenone (yield 77.6%), yellow liquid .

[0033] (2) Synthesis of 3,5-dimethylphenol ethyl ester:

[0034] Add 0.5mol of 3,5-dimethylacetophenone into 1000ml of dichloromethane, add 1.0mol of perox...

Embodiment 3

[0038] (1) Synthesis of 3,5-dimethylacetophenone:

[0039] Add 1.0 mol of acetyl chloride dropwise to the mixture of aluminum trichloride and mixed xylene (2.0 mol of aluminum trichloride and 5.0 mol of xylene) under the condition of ice-water bath, control the dropping temperature not to exceed 15°C, and finish adding Afterwards, the temperature was raised to 100° C. and stirred for 5 h. After the reaction, the reaction solution was poured into 1000 ml of ice water. The organic phase was separated, and washed with 0.5% dilute hydrochloric acid, saturated sodium carbonate solution, and water until neutral. After drying with anhydrous sodium sulfate, concentrate under reduced pressure, rectify the concentrate under reduced pressure, and collect the fraction at 94~98℃ / 5 mmHg, which is the product 3,5-dimethylacetophenone (yield 82.3%), yellow liquid.

[0040] (2) Synthesis of 3,5-dimethylphenol ethyl ester:

[0041] Add 0.5mol of 3,5-dimethylacetophenone into 1000ml of ethyl...

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Abstract

The invention provides a preparation method of 3,5-dimethylphenol. The method comprises the following steps: xylene (one or a mixture of o-xylene, m-xylene and p-xylene) and alkyl halide or anhydride are subjected to a reaction under the effect of a catalyst, and an intermediate 3,5-dimethylcarbonyl compound is produced under a certain condition; the intermediate is oxidized under the effect of a peroxide, such that 3,5-dimethylphenol ester is produced; and 3,5-dimethylphenol ester is hydrolyzed, such that 3,5-dimethylphenol is obtained. According to the method, xylene is adopted as an initial raw material, and is processed through the tree steps of carbonylation, oxidation and hydrolysis, such that a target product can be prepared with high yield. Therefore, an assumption of synthesizing 3,5-dimethylphenol with high yield under a mild condition is made possible. Compared to prior arts, the method provided by the invention has the advantages of low raw material cost, less three-waste, and mild reaction condition. The method is especially suitable for large-scale productions.

Description

technical field [0001] The invention belongs to the field of fine chemical industry. The Bayer-Villiger oxidation reaction is used to design a preparation method of 3,5-dimethylphenol with high yield and mild reaction conditions. Background technique [0002] 3,5-Dimethylphenol is an important fine chemical intermediate and pharmaceutical intermediate, mainly used in the preparation of antioxidants, antimicrobials, resin adhesives and preservatives. The traditional 3,5-dimethylphenol industrialization technologies mainly include coal tar wash oil fraction separation method, phenol alkylation method (Coal liquefaction and upgrading benefit from heteroatom removal. Coal Science and Technology , 1987.) and m-xylene sulfonation alkali fusion method (synthesis of 3,5-xylenol by sulfonation alkali fusion method. Liaoning Chemical Industry, 1977) and other liquid phase synthesis methods. These production processes have disadvantages such as long reaction route, slow reaction rate,...

Claims

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Application Information

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IPC IPC(8): C07C39/07C07C37/055
Inventor 李维平刘晓波孙燕超李晓明王芳芳于莹莹孙朋波
Owner RONGCHENG QINGMU CHEM MATERIALS
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