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Method for synthesizing vanillin from eugenol through ozone oxidation

A technology of ozone oxidation and vanillin, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve problems such as low production yield and difficult wastewater treatment, and achieve fast reaction rate and less pollution , the effect of high yield

Pending Publication Date: 2020-12-22
成都三香汇香料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In view of the above-mentioned shortcoming of the prior art, the object of the present invention is to provide a kind of method for synthesizing vanillin through ozonation of eugenol, for solving the production yield of eugenol method in the prior art is low, uses metal oxidant, The problem of difficult wastewater treatment, eugenol isomerization uses triphenylphosphine ruthenium chloride as a catalyst, no wastewater is generated during the process, and isoeugenol acetate is oxidized by ozone, which avoids the use of heavy metal oxidants, which is in line with the trend of green development. The process has the advantages of environmental protection and high yield

Method used

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  • Method for synthesizing vanillin from eugenol through ozone oxidation
  • Method for synthesizing vanillin from eugenol through ozone oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The method that eugenol synthesizes vanillin through ozone oxidation, comprises the steps:

[0055] 1. Isomerization reaction:

[0056] Add 500 g of eugenol and 4.0 g of catalyst triphenylphosphine ruthenium chloride into the reactor and mix evenly, heat to 50-60° C. and keep the temperature for reaction for 4 hours until the content of eugenol is lower than 1%. Then directly carry out vacuum distillation to obtain 495 g of isoeugenol with a content of 98.5%, and the mass yield is 99%.

[0057] Add 500g of eugenol and 1g of new catalyst to the catalyst and part of the organic matter in the remaining kettle in the above example, and heat to 50-60°C to keep the temperature for 4-5 hours. When the eugenol content was lower than 1%, vacuum distillation was directly carried out to obtain 496 g of isoeugenol with a content of 98.4%, and the mass yield was 99%.

[0058] 2. Esterification reaction:

[0059] Add 10g of anhydrous sodium carbonate and 390g of acetic anhydride i...

Embodiment 2

[0067] The method that eugenol synthesizes vanillin through ozone oxidation, comprises the steps:

[0068] 1. Isomerization reaction:

[0069] Add 500 g of eugenol and 3.0 g of catalyst triphenylphosphine ruthenium chloride into the reactor and mix evenly, heat to 60-80° C. and keep the temperature for reaction for 4 hours until the content of eugenol is lower than 1%. Then directly carry out vacuum distillation to obtain 495 g of isoeugenol with a content of 98.5%, and the mass yield is 99%.

[0070] Add 500g of eugenol and 2g of new catalyst to the catalyst and part of the organic matter in the remaining kettle in the above example, and still heat to 60-80°C and keep the temperature for 5.0h. When the eugenol content was lower than 1%, vacuum distillation was directly carried out to obtain 495 g of isoeugenol with a content of 98.6%, and the mass yield was 99%.

[0071] 2. Esterification reaction:

[0072] Add 20g of anhydrous sodium acetate and 360g of acetic anhydride i...

Embodiment 3

[0079] The method that eugenol synthesizes vanillin through ozone oxidation, comprises the steps:

[0080] 1. Isomerization reaction:

[0081] Add 500 g of eugenol and 0.1 g of catalyst triphenylphosphine ruthenium chloride into the reactor and mix evenly, heat to 120-150°C and keep the temperature for reaction for 6 hours until the content of eugenol is lower than 1%. Then directly carry out vacuum distillation to obtain 491 g of isoeugenol with a content of 98.8%, and the mass yield is 98%.

[0082] Add 500g of eugenol and 0.03g of new catalyst to the catalyst and part of the organic matter in the remaining kettle in the above example, and heat to 120-150°C to keep the temperature for 4-5 hours. When the eugenol content was lower than 1%, vacuum distillation was directly carried out to obtain 495 g of isoeugenol with a content of 98.4%, and the mass yield was 99%.

[0083] 2. Esterification reaction:

[0084] Add 25g of anhydrous sodium carbonate and 400g of acetic anhydr...

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Abstract

The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing vanillin from eugenol through ozone oxidation. The method comprises the followingsteps: adding dichlorotris(triphenylphosphine)ruthenium serving as a catalyst into eugenol to perform isomerization reaction to obtain isoeugenol, performing esterification reaction to obtain isoeugenol acetate, performing ozonation, and performing reducing; and carrying out alcoholysis and refining on the acetyl vanillin to obtain a pure product. The method solves the problems of low productionyield, use of a metal oxidant and difficult treatment of wastewater in the eugenol method in the prior art, eugenol isomerization adopts dichlorotris(triphenylphosphine)ruthenium as a catalyst, no wastewater is generated in the process, isoeugenol acetate is oxidized by ozone, the use of a heavy metal oxidant is avoided, and the method conforms to the green development trend. The method has the advantages of environmental protection and high yield.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing vanillin through ozone oxidation of eugenol. Background technique [0002] Vanillin is one of the important food spices, and it is a food flavoring agent. It has vanilla bean aroma and strong milky aroma. It is an indispensable and important raw material in the food additive industry. It is widely used in various needs to increase milky aroma. Flavoring food, such as cakes, cold drinks, chocolate, candy, biscuits, instant noodles, bread and tobacco, flavored wine, toothpaste, soap, perfume, cosmetics, ice cream, beverages and daily cosmetics to enhance and stabilize fragrance effect. It can also be used in soap, toothpaste, rubber, plastic, and pharmaceuticals. Comply with FCCⅣ standard. [0003] Vanillin has a wide range of applications in foreign countries. It is widely used in the production of pharmaceutical intermediates, and i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/64C07C47/58
CPCC07C45/64C07C41/32C07C67/08C07C67/29C07C47/58C07C43/23C07C69/157
Inventor 李良龙李威宏
Owner 成都三香汇香料有限公司
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