Method for preparing galaxolide under catalysis of superfine aluminum trichloride

A technology of fine aluminum trichloride and Jiale musk, applied in the direction of organic chemistry, can solve the problems of poor reproducibility, low reaction conversion rate and yield, long reaction time, etc., achieve good reproducibility and improve production efficiency , the effect of reducing energy consumption

Inactive Publication Date: 2019-12-13
ANHUI JINGHE IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the existing problems such as relatively poor reproducibility of the reaction, low reaction conversion rate and yield, long reaction time, etc. Catalyzed method for preparing Jiale musk by superfine aluminum trichloride

Method used

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  • Method for preparing galaxolide under catalysis of superfine aluminum trichloride
  • Method for preparing galaxolide under catalysis of superfine aluminum trichloride

Examples

Experimental program
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Effect test

Embodiment 1

[0023] (1) In a 1000 ml three-neck round bottom flask, add 147 grams of pentamethylindane (80% purity), 142 grams of chlorobenzene and 88 grams of anhydrous aluminum trichloride powder with a particle size of 60 mesh, stir and cool to -20 degrees Celsius;

[0024] (2) Add dropwise a mixed solution of 50 grams of propylene oxide and 100 grams of chlorobenzene to the solution in step (1), and the dropwise addition is completed in about 2 to 3 hours, and continue to react at -20 degrees Celsius for 2 hours, and then slowly add 15 grams of water was added dropwise in about 0.5 hours, then the cold bath was removed, 44 grams of dimethoxymethane was added dropwise, the addition was completed in about 0.5 hours, and the reaction was continued for 2 hours at 25 degrees Celsius;

[0025] (3) Slowly add 375 grams of water dropwise to the reaction solution in step (2), and add it in about 0.5 hours. After the addition, stir for 1 hour, let it stand for 0.5 hours, separate the organic lay...

Embodiment 2

[0028] Contrast experiment, other conditions and operation are identical with embodiment 1, only difference is, use the granular anhydrous aluminum trichloride powder of 4~10 millimeters of particle diameters to replace 60 mesh anhydrous aluminum trichloride powders, reaction The conversion rate is 21% in terms of pentamethylindan, and the reaction yield is 12% (based on the consumption of pentamethylindan, the reaction yield is 57%).

Embodiment 3

[0030] (1) In a 1000 ml three-neck round bottom flask, add 149 grams of pentamethylindane (81% purity), 145 grams of chlorobenzene and 89 grams of anhydrous aluminum trichloride powder with a particle size of 100 mesh, stir and cool to -25 degrees Celsius;

[0031] (2) Add dropwise a mixed solution of 51 grams of propylene oxide and 100 grams of chlorobenzene to the solution in step (1), and the dropwise addition is completed in about 2 to 3 hours, and continue to react at -25 degrees Celsius for 2 hours, and then slowly add 30 grams of methanol was added dropwise in about 0.5 hours, then the cold bath was removed, 20 grams of paraformaldehyde was added dropwise, the addition was completed in about 0.5 hours, and the reaction was continued for 2 hours at 25 degrees Celsius;

[0032] (3) Slowly add 380 grams of water dropwise to the reaction solution in step (2), and add it in about 0.5 hours. After the addition, stir for 1 hour, let it stand for 0.5 hours, separate the organic...

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Abstract

The invention relates to a method for preparing galaxolide under catalysis of superfine aluminum trichloride. The method is characterized by comprising the following steps: 1, adding pentamethyl indanand anhydrous aluminum trichloride with particle size of 5 meshes or blow to a solvent, and cooling the solution to subzero 30-subzero 20 DEG C, wherein the mass ratio of the pentamethyl indan to anhydrous aluminum trichloride is (1.5-2):1; 2, dropwise adding propylene oxide to dissolve in the solution in the solvent during stirring, and conducting a reaction at subzero 30-subzero 5 DEG C for 1-2h to produce hexamethyl indanol, wherein the mass ratio of the propylene oxide to pentamethyl indan is (0.3-0.5):1; 3, continuously adding a deactivating agent and formaldehyde or formaldehyde equivalents, heating the mixture to 5-65 DEG C to react for 0.5-4 h to produce galaxolide, wherein the molar ratio of the deactivating agent, the formaldehyde or formaldehyde equivalents to the pentamethylindan is (1-2):1 and (0.5-1):1; and 4, performing purification. The method has the advantages as follows: aluminum trichloride powder with superfine particle size is used, the raw material conversionrate and product yield are significantly increased, the reaction time is shortened, the reaction has good reproducibility, energy is saved, production efficiency is improved, and the production cost is reduced.

Description

technical field [0001] The invention belongs to the field of preparation of flavors and fragrances, and relates to the preparation of Jiale musk, in particular to a method for preparing Jiale musk catalyzed by ultrafine aluminum trichloride. Background technique [0002] Jiale musk (Galaxolide ® ), chemical name 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-γ-2-benzopyran, is an international flavor and fragrance The company (IFF) successfully developed the tricyclic heterochromatic fragrance in the 1960s, which has a strong musky smell and is widely used in daily chemical, perfume and other industries. [0003] There are many synthetic routes for Jiale musk (patent publication number is US3360530), so far, the most direct and economical route is: pentamethylindane (I) and propylene oxide in Lewis acid (usually aluminum trichloride) Under the action of Friedel–Crafts alkylation, hexamethylindanol (II) is produced, and hexamethylindanol (II) continues to undergo a ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94
CPCC07D311/94
Inventor 易健康傅绪飞胡青阳
Owner ANHUI JINGHE IND
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