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Method for synthesizing pseudoisomethyl ionone

A technology of isomethyl ionone and a synthesis method, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of large influence on the aroma of the final product, complex condensation products, difficult post-processing and the like , to improve product quality, reduce heat loss, and increase the frequency of gas-liquid exchange

Inactive Publication Date: 2004-10-20
广州百花香料股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because this method is not suitable for the synthesis of pseudoisomethyl ionone with butanone-2 as raw material, it mainly shows that the condensation product is complicated, generates high boiling point by-products, post-treatment is difficult and the yield is low, and the phase transfer catalyst The use of the product has a greater impact on the aroma of the final product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In a 2000L three-necked flask with a stirrer, a thermometer and a dropping funnel, add butanone-2 610g and methanol 880g, potassium hydroxide 43g, antioxidant 10105g, at room temperature, add 98% citral evenly dropwise 155g was added in 2 hours and 20 minutes, the reaction was completed after continuing the insulation reaction for 2 hours, acetic acid was added for neutralization, and pH=6.8 was controlled, and then butanone and methanol were recovered under conditions of 90° C. lower than the liquid temperature. After the recovery was completed, in the reaction mass Add 300 g of clear water, stir for 10 minutes, after static layering, 241 g of crude oil layer is obtained, add 7 g of isooctyl phthalate to the crude product, and carry out vacuum distillation after mixing evenly, and collect fractions in the interval of 138~143 ℃ / 0.53KPa 197.5 g of pseudo-isomethyl ionone and its isomer products were obtained, the content of which was analyzed by gas chromatography was 94....

Embodiment 2

[0015] In a 2000L three-necked flask with a stirrer, a thermometer and a dropping funnel, add 580g of butanone-2 and 621g of isopropanol, 34g of sodium hydroxide, and an antioxidant 2,6-di-tert-butyl-4-hydroxyl 3 g of cresol, 155 g of content 98% citral was added dropwise in 1 hour and 48 minutes, the control temperature was between 30 and 32 ° C, and the insulation reaction was continued for 2 hours and 30 minutes. After the reaction was completed, methyl formate was added for neutralization, and pH=6.5 , then reclaim butanone and isopropanol under the condition that liquid temperature is lower than 90 ℃, add clear water 300g in the there-necked flask after recovery, stir for 10 minutes, get oil layer crude product 235g after static layering, add dioctyl phthalate 5 g of ester was distilled under reduced pressure, and the products with fractions between 138 and 143° C. / 0.53 KPa were collected to obtain 198 g of pseudoisomethyl ionone and its isomer products, the content of whi...

Embodiment 3

[0017] In a 2000L three-necked flask with a stirrer, a thermometer and a dropping funnel, add a total of 540g of butanone-2 and 810g of ethanol, 21g of lithium hydroxide, and 4g of antioxidant tert-butyl-4-hydroxyanisole. In 32 minutes, 155g of citral with a content of 98% was added dropwise, and the temperature was controlled between 23 and 28°C. After the addition, the reaction was continued for 2 hours and 30 minutes, and methyl formate was added for neutralization. Recover methyl ethyl ketone and ethanol under the condition of lower than 90°C, add about 300g of clear water after recovery, stir for 10 minutes, obtain crude oil layer 236g after static layering, add 3.5g of dioctyl phthalate, and carry out vacuum distillation after mixing. , the fractions meeting the conditions of 138-143°C / 0.53KPa were collected to obtain 198 g of pseudo-isomethyl ionone and its isomer products, the content of which was 94.6% by gas chromatography, and the yield was 94.2%.

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Abstract

The method for synthesizing pseudoisomethyl ionone-intermediate product of perfume includes the following steps: in butanone-2, adding or no adding organic solvent, alkali or alkali earth metal hydroxide and inhibitor in turn, the mole ratio of alkali and citral is 0.75-0.9:1, the mole ratio of inhibitor and citral is 0.0101-0.02:1, and according to the mole ratio of citral and butanone-2 which is 1:7-13 drop-adding citral, dropp-adding time is 1-3 hr. reaction temp. is 20-40 deg.C and reaction time is 4-6 hr. After the reaction is completed, recovering solvent and butanone-2, using acetic acid or methyl formate to neutralize residual material to make pH by 6.5-6.8, washing with clean water, adding plasticizer in oil layer to make fractionation, addition quantity of plasticizer is 1-5% of oil layer weight, and obtain pseudoisomethyl ionone.

Description

technical field [0001] The invention relates to a method for synthesizing a fragrance intermediate, in particular to a method for synthesizing an isomethyl ionone fragrance intermediate. Background technique [0002] Isomethylionone is a traditional synthetic fragrance, pale yellow to yellow liquid with a pure aroma, violet-like floral aroma of sweet wood. Usually, it is synthesized through two-step reaction, firstly, Claisen-Schmidt condensation reaction of citral (Panthera japonica oil) and butanone-2 occurs in alkaline solution to obtain the intermediate pseudo-isomethyl. base ionone; secondly, pseudo-isomethyl ionone undergoes a cyclization reaction in an acidic medium to generate isomethyl ionone. Isomethyl ionone is usually a mixture of multiple isomers, of which α-isomethyl ionone has typical aroma characteristics, and its content directly affects the quality of the product, so the synthetic process of pseudo-isomethyl ionone is crucial. [0003] Chinese Patent No....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/72C07C49/203
Inventor 甄宏爝宋春玲陈图雄胡顺琼钟炼军
Owner 广州百花香料股份有限公司