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Method for synthesizing pseudoisomethyl ionone

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

Inactive Publication Date: 2003-02-05
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 610 g of butanone-2, 880 g of methanol, 43 g of potassium hydroxide, and 1010 5 g of antioxidants. At room temperature, evenly add citral with a content of 98% 155g, add in 2 hours and 20 minutes, continue to keep warm for 2 hours, then the reaction is over, add acetic acid to neutralize, control pH = 6.8, then recover methyl ethyl ketone and methanol under the condition of 90°C lower than the liquid temperature, after the recovery is completed, the reaction material Add 300g of clean water, stir for 10 minutes, and obtain 241g of crude product of the oil layer after static layering. Add 7g of isodioctyl phthalate to the crude product, mix well and carry out vacuum distillation, and collect fractions in the range of 138~143℃ / 0.53KPa The product obtained was 197.5 g of pseudoisomethyl ionone and its isomer products, the gas chromatography analysis content was 94.4%, and the yield was 9...

Embodiment 2

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

Embodiment 3

[0017] In a 2000L three-necked flask with a stirrer, a thermometer, and a dropping funnel, add a total of 540 g of butanone-2 and 810 g of ethanol, 21 g of lithium hydroxide, and 4 g of antioxidant tert-butyl-4-hydroxyanisole. Add 155g of citral with a content of 98% dropwise in 32 minutes, control the temperature between 23 and 28°C, continue to keep warm for 2 hours and 30 minutes after the addition, then add methyl formate for neutralization, control the pH=6.8, and then Recover methyl ethyl ketone and ethanol at a temperature lower than 90°C. After recovery, add about 300g of clear water, stir for 10 minutes, and obtain 236g of crude product in the oil layer after static separation. Add 3.5g of dioctyl phthalate, mix well, and conduct vacuum distillation , collecting fractions meeting the conditions of 138-143° C. / 0.53 KPa to obtain 198 g of pseudoisomethylionone and its isomer products, the content of gas chromatography analysis was 94.6%, 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 synthesis method of a fragrance intermediate, in particular to a synthesis method of an isomethyl ionone fragrance intermediate. Background technique [0002] Isomethylionone is a traditional synthetic fragrance, in the form of pale yellow to yellow liquid, with a pure aroma and sweet woody violet-like floral aroma. It is usually synthesized through a two-step reaction. First, the Claisen-Schmidt condensation reaction occurs between citral (Litsea cubeba oil) and butanone-2 in alkaline solution to obtain the intermediate pseudoisomethyl ionone; secondly, pseudoisomethyl ionone. Methyl ionone undergoes a cyclization reaction in acidic medium to generate isomethyl ionone. Isomethyl ionone is usually a mixture of multiple isomers, among which α-isomethyl ionone has typical aroma characteristics, and its content directly affects the quality of the product, so the synthesis process of pseudoisomethyl ionone is crucial. [0003]...

Claims

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Application Information

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Patent Type & Authority Applications(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
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