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Method for improving content of cis-methyl-dihydrojasmonate

A technology of methyl dihydrojasmonate and cis, which is applied in the field of increasing the content of spices, can solve the problems of not particularly high requirements for cis content, expensive catalysts, and high product prices, so as to shorten the conversion time and optimize Product quality, the effect of improving conversion efficiency

Active Publication Date: 2012-10-03
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Comparing the above two aspects, although the former method has obtained a product with a high cis content, the catalyst used in the research is expensive, which makes the cost very high, and the price of the product obtained by synthesis is very expensive; although the latter method converts the trans to cis The yield of the cis-form is not very high, but because it is cheap and the product does not require a particularly high cis-content, it is still a research hotspot in the spice industry

Method used

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  • Method for improving content of cis-methyl-dihydrojasmonate
  • Method for improving content of cis-methyl-dihydrojasmonate
  • Method for improving content of cis-methyl-dihydrojasmonate

Examples

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Embodiment 1

[0020] The present invention is specifically described below through the examples, it is necessary to point out that the examples are only used to further illustrate the present invention, and can not be interpreted as limiting the protection scope of the present invention, those skilled in the art can make some according to the above-mentioned content Non-essential improvement and adjustment; in addition, it should be noted that the product after the conversion of the present invention is not distilled, and as the content of the cis-dihydrojasmonate methyl ester product needs to be further improved according to the present invention, after the conversion reaction is completed , the content of the cis-isomer can be increased by distillation. The selection of the transformation condition of embodiment 1, methyl dihydrojasmonate isomer

[0021] The raw materials used in this example are mixed cis-trans isomers of methyl dihydrojasmonate, wherein the cis-isomer content is 6%, the...

Embodiment 2

[0045] Take by weighing a part of 20g trans-methyl dihydrojasmonate isomers, stir after adding 0.22g sodium carbonate catalyst, make the catalyst fully dissolved in the liquid, then transfer in the three-necked flask with reflux device; Put the three-necked flask into the microwave device and ventilate it with nitrogen, set the power of the microwave to 0.4kw, and react for 7 minutes; after the reaction, take out the flask and quickly pour the product into ice water, and stir rapidly, control the temperature below 30°C, and adjust the pH value to neutral , moved into a separatory funnel to stand for stratification, took out the organic layer, dried with anhydrous sodium sulfate for 24 hours, and detected with gas chromatography; the gas chromatography test result cis-dihydrojasmonate methyl ester content was 15.2%; the above method obtained The detection of the product is to use the peak area normalization method to test the cis-trans isomer content with a gas chromatograph. Th...

Embodiment 3

[0047] Take by weighing a part of 20g trans-methyl dihydrojasmonate isomer, stir after adding 0.25g sodium sulfate catalyst, make the catalyst fully dissolve in the liquid, then transfer in the three-necked flask with reflux device; Put the three-necked flask into the microwave device and pass nitrogen gas, set the power of the microwave to 0.5kw, and react for 4 minutes; after the reaction, take out the flask and pour the product into ice water quickly, and stir quickly, control the temperature below 30°C, and adjust the pH value to neutral , moved into a separatory funnel to stand for layering, took out the organic layer, dried it with anhydrous calcium chloride for 24 hours, and detected it with gas chromatography; as a result of gas chromatography test, the content of methyl cis dihydrojasmonate was 15.3%.

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Abstract

The invention discloses a method for improving the content of cis-methyl-dihydrojasmonate, which comprises the following steps: filling an object to be converted and a catalyst into a reactor, and putting the reactor into a microwave device; introducing nitrogen into the reactor and starting the microwave device; and after the reaction, introducing the reactants into ice water with a neutral pH value for quick cooling and standing layering, and drying an organic layer to obtain the product, wherein the object to be converted is cis-trans mixed methyl dihydrojasmonate isomer or trans-methyl-dihydrojasmonate, the catalyst is sodium carbonate, sodium sulfate, sodium chloride, calcium chloride, copper chloride or zinc chloride, the mass ratio of the object to be converted to the catalyst is 80-90:1, the microwave power is between 0.2 and 0.5 kW, the reaction time is between 2 and 10 minutes, the temperature of the ice water is less than 40 DEG C, and the drying agent used for drying the organic layer is anhydrous sodium sulfate, calcium chloride, or a 4A molecular sieve. The method improves the cis-content and shortens the conversion time, and as a higher cis-product, after dilution, the cis-methyl-dihydrojasmonate can be directly used for preparing an aromatic product, purifying the smell of the aromatic product and optimizing the product quality.

Description

technical field [0001] The invention relates to a method for increasing the content of spices in the perfume industry, in particular to a method for increasing the content of methyl cis-dihydrojasmonate. Background technique [0002] Jasmine is a kind of floral fragrance that people like, and methyldihydrojasmonate (Methyldihydrojasmonate CAS: 24851-98-7FEMA: 3408) has an elegant and soft jasmine fragrance and a comfortable lemon-like fruity fragrance. The whole fragrance is light Elegant, long-lasting fragrance, good fragrance effect, so it becomes one of the main compounds to prepare the characteristic aroma of jasmine. Since E. Demole and others separated methyl jasmonate from jasmine essential oil in the 1960s and hydrogenated it to obtain methyl dihydrojasmonate, Firmenich has successfully applied it in the famous perfume "EauSauvage" (Dior), And came out under the trade name of "Hedione", it has become one of the most consumed and most successful synthetic fragrances....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/716C07C67/333B01J27/232B01J27/055B01J27/10C11B9/00
Inventor 吕金顺陈兆刚阚玉和夏士朋安礼涛赵新年
Owner HUAIAN WAN BANG SPICE IND CO LTD
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