Preparation method of tetrahydroionone

A technology of ionone and hydrogen, which is applied in the field of preparation of tetrahydroionone, can solve the problems of high hydrogen pressure and high hydrogenation reaction temperature, achieve good reaction effect, improve yield and purity

Inactive Publication Date: 2018-07-27
WUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method can solve the existing problems of high hydrogenation reaction temperature and high hydrogen pressure, is

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) 40g content is 97.1% ionone and 1.2g Raney nickel catalyst to add in autoclave, add 88g ethanol and 0.2g triethanolamine, i.e. the mass ratio of ionone, Raney nickel catalyst, solvent and stabilizer 1:0.03:2.2:0.005. Replace the air in the autoclave with nitrogen for three times, then replace it with hydrogen for three times, and finally introduce hydrogen again to control the hydrogen pressure in the autoclave to 0.5 MPa. The reaction temperature of the materials in the high-pressure reactor was kept at 40° C., and the pressure-holding and heat-insulating reaction was carried out. After 2 hours of reaction, sample analysis was started, so as to adjust the reaction conditions of subsequent reactions according to the content changes of raw material ionone, intermediate product dihydroionone and product tetrahydroionone.

[0025] (2) When the ionone content in the autoclave is less than or equal to 3%, adjust the hydrogen pressure to 1.0 MPa, adjust the reaction temp...

Embodiment 2

[0032] (1) 100g content is 96.8% ionone and 2g Raney's nickel catalyst to add in autoclave, add 190g ethanol and 0.35g triethanolamine, promptly the mass ratio of ionone, Raney's nickel catalyst, solvent and stabilizer is 1:0.02:1.9:0.0035. Replace the air in the autoclave with nitrogen for three times, then replace it with hydrogen for three times, and finally introduce hydrogen again to control the hydrogen pressure in the autoclave to 0.7MPa. The reaction temperature of the materials in the high-pressure reactor was kept at 45° C., and the pressure-holding and heat-insulating reaction was carried out. After 2 hours of reaction, sample analysis was started, so as to adjust the reaction conditions of subsequent reactions according to the content changes of raw material ionone, intermediate product dihydroionone and product tetrahydroionone.

[0033] (2) When the ionone content in the autoclave is less than or equal to 3%, adjust the hydrogen pressure to 1.2 MPa, adjust the r...

Embodiment 3

[0040](1) 400g content is 96.2% ionone and 4g Raney's nickel catalyst to add in autoclave, add 640g ethanol and 0.8g triethanolamine, promptly the mass ratio of ionone, Raney's nickel catalyst, solvent and stabilizer is 1:0.01:1.66:0.002. Replace the air in the autoclave with nitrogen for three times, then replace it with hydrogen for three times, and finally introduce hydrogen again to control the hydrogen pressure in the autoclave to 1MPa. The reaction temperature of the materials in the high-pressure reactor was kept at 50° C., and the pressure-holding and heat-insulating reaction was carried out. After 2 hours of reaction, sample analysis was started, so as to adjust the reaction conditions of subsequent reactions according to the content changes of raw material ionone, intermediate product dihydroionone and product tetrahydroionone.

[0041] (2) When the ionone content in the autoclave is less than or equal to 3%, adjust the hydrogen pressure to 1.5 MPa, adjust the react...

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PUM

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Abstract

The invention discloses a preparation method of tetrahydroionone. The preparation method includes: putting ionone and Raney nickel catalyst into a high-pressure reaction kettle, adding solvent and stabilizer, feeding hydrogen, controlling hydrogen pressure in the high-pressure reaction kettle and reaction temperature of materials for pressure-maintaining heat-holding reaction under reaction conditions, constantly performing sampling and analysis, and adjusting reaction conditions of subsequent reaction according to content change of raw material ionone and intermediate product dihydroionone; when dihydroionone content in the high-pressure reaction kettle is less than or equal to 2%, stopping adding hydrogen into the high-pressure reaction kettle and stopping heating the materials, using nitrogen to replace hydrogen in the high-pressure reaction kettle, and stopping reaction; after the materials are cooled, settling, filtering, and discharging to obtain tetrahydroionone. The method cansolve the problem that hydrogenation reaction is high in reaction temperature and hydrogen pressure, is environment-friendly, low in energy consumption and safe and has the advantages of high yield and high product purity.

Description

technical field [0001] The invention relates to a preparation method of terpenoids, in particular to a preparation method of tetrahydroionone. Background technique [0002] Tetrahydroionone, also known as 6,10-dimethyl-9-undecen-2-one, has the molecular formula C 13 h 24 O, with a molecular weight of 196.33, is a synthetic organic compound. Tetrahydroionone has woody, floral and fruity aromas, like violets, roses, and sweet fruit flavors, with a slight apple and peach aroma, and is used for essence. Tetrahydroionone can be prepared by hydrogenating ionone in the presence of colloidal palladium, or by reacting linalool, acetic anhydride and sodium ethoxide followed by hydrogenation, or by reacting geraniol with acid chloride. Tetrahydroionone is mostly prepared from ionone through hydrogenation catalysis. At present, there are no relevant literature reports and industrial production. Contents of the invention [0003] The object of the present invention is to provide a ...

Claims

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Application Information

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IPC IPC(8): C07C49/11C07C49/21C07C45/62C07C45/82
CPCC07C45/62C07C45/82C07C49/21C07C49/11
Inventor 杨韶平刘娟娟
Owner WUZHOU UNIV
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