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Method for synthesizing 1,8-cineole from terpilenol

A technology for terpineol and cineole, which is applied in the field of 1,8-cineole synthesis, can solve the problems of complex steps, difficult to control purity, low yield and the like, and achieves easy operation, short reaction time and high yield. Effect

Inactive Publication Date: 2018-09-21
YUNNAN LORRAINE AROMATIC PROD CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to provide a method for synthesizing 1,8-cineole from terpineol to solve the problems of low yield, complicated steps and difficulty in controlling the purity in the existing chemical synthesis of 1,8-cineole

Method used

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  • Method for synthesizing 1,8-cineole from terpilenol
  • Method for synthesizing 1,8-cineole from terpilenol
  • Method for synthesizing 1,8-cineole from terpilenol

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Experimental program
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Effect test

Embodiment 1

[0025] The method that terpineol synthesizes 1,8-cineole comprises the steps:

[0026] 1) The mass ratio of terpineol to dichloromethane is 1:13, and the mass ratio of terpineol to solid catalyst zinc trifluoromethanesulfonate is 1:10.4 into the reaction flask; under normal temperature and pressure, under nitrogen protection Stir with a stirrer for 4 hours at a speed of 80 rpm, and let it stand for 25 minutes after the reaction is completed to obtain the reaction solution I;

[0027] 2) Add dichloromethane to the reaction solution I, the mass ratio of terpineol to dichloromethane is 1:6, stir with a stirrer for 1 hour, and the rotation speed is 40 rpm to obtain the reaction solution II;

[0028] 3) Add saturated sodium bicarbonate solution to reaction solution II for extraction, the mass ratio of terpineol to saturated sodium bicarbonate solution is 1:19, let the layers stand for 10 minutes, and remove the lower layer solution to obtain reaction solution III;

[0029] 4) Wash...

Embodiment 2

[0031] The method that terpineol synthesizes 1,8-cineole comprises the steps:

[0032] 1) The mass ratio of terpineol to dichloromethane is 1:8, and the mass ratio of terpineol to solid catalyst zinc trifluoromethanesulfonate is 1:7.4 and added to the reaction flask; under normal temperature and pressure, under nitrogen protection Stir with a stirrer for 4 hours at a speed of 85 rpm, and let it stand for 25 minutes after the reaction is complete to obtain a reaction solution I;

[0033] 2) Add dichloromethane to the reaction solution I, the mass ratio of terpineol to dichloromethane is 1:4.5, stir with a stirrer for 1 hour, and the rotation speed is 45 rpm to obtain the reaction solution II;

[0034] 3) Add saturated sodium bicarbonate solution to reaction solution II for extraction, the mass ratio of terpineol to saturated sodium bicarbonate solution is 1:13.5, let the layers stand for 10 minutes, and remove the lower layer solution to obtain reaction solution III;

[0035] ...

Embodiment 3

[0037] The method that terpineol synthesizes 1,8-cineole comprises the steps:

[0038] 1) The mass ratio of terpineol to dichloromethane is 1:3.5, and the mass ratio of terpineol to solid catalyst zinc trifluoromethanesulfonate is 1:4.3 into the reaction flask; under normal temperature and pressure, under nitrogen protection Stir with a stirrer for 4 hours at a speed of 90 rpm, and let stand for 25 minutes after the reaction is complete to obtain a reaction solution I;

[0039] 2) Add dichloromethane to the reaction solution I, the mass ratio of terpineol to dichloromethane is 1:2.8, stir with a stirrer for 1 hour, and the rotation speed is 50 rpm to obtain the reaction solution II;

[0040] 3) adding saturated sodium bicarbonate solution to the reaction solution II for extraction, the mass ratio of terpineol to saturated sodium bicarbonate solution was 1:8.2, standing for 10 minutes, and removing the lower layer solution to obtain reaction solution III;

[0041] 4) Wash the ...

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Abstract

The invention discloses a method for synthesizing 1,8-cineole from terpilenol, and relates to the technical field of synthesis of 1,8-cineole. Terpilenol is converted into 1,8-cineole through heterogeneous catalysis with zinc trifluorosulfonate or copper trifluorosulfonate as the catalyst. Terpilenol, dichloromethane and a solid catalyst are added into a reaction bulb for a stirring reaction through a stirrer under the protection of nitrogen at normal temperature and normal pressure, and the interference of an external environment is avoided. Dichloromethane diluted reaction liquid is added after the reaction is completed, a saturated sodium bicarbonate solution is added for extraction, a dichloromethane phase is synthesized and washed three times with a saturated salt solution, anhydroussodium sulfate is added for drying, and an organic phase is concentrated to obtain 1,8-cineole with certain purity. It is verified through experiments that the terpilenol conversion rate is up to 98%and the effective conversion rate of 1,8-cineole reaches 60% or above. Terpilenol is low in price and easy to obtain when serving as the raw material, and the production cost is reduced; high temperature, high pressure and other strict conditions are avoided, the technological steps are simple, the reaction time is short, and the conversion rate is high; no harmful byproducts can be generated, andthe method is friendly to the environment.

Description

technical field [0001] The invention relates to the technical field of 1,8-cineole synthesis, in particular to a method for synthesizing 1,8-cineole from terpineol. Background technique [0002] 1,8-cineole is the main component of eucalyptus oil, which is mainly used in hygiene and pharmaceutical products. High-purity 1,8-cineole products have special value in some oral medicines (such as cough syrup, chewing gum) and food flavors. 1,8-cineole is mainly extracted from natural product eucalyptus oil, but due to limited natural resources and many impurities in eucalyptus oil, it is difficult to obtain high-purity 1,8-cineole products to satisfy the market need. At present, in the existing domestic experimental reports, there are studies on the synthesis of 1,8-cineole by chemical means, but the yield of the experimental results is low, the technical steps are relatively complicated, the purity of the product is difficult to control, and some difficult-to-handle clean, The ...

Claims

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Application Information

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IPC IPC(8): C07D493/08
CPCC07D493/08
Inventor 胡翔飞叶志恒
Owner YUNNAN LORRAINE AROMATIC PROD CO LTD
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