A kind of preparation method of methyl ionone and intermediate thereof

A technology for methyl ionone and intermediates, applied in the fields of fragrance chemistry and fine chemicals, can solve the problems of waste of alkali, cumbersome process, unspecified proportion of pseudo-isomethyl ionone, etc., and achieve cost reduction and lighten Effects of Environmental Pollution

Active Publication Date: 2020-03-27
ZHEJIANG NHU CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the higher yield is mentioned in the literature, the ratio of pseudo-isomethyl ionone and pseudo-n-methyl ionone is not specified; Treatment of alkali catalysts produces more three wastes
[0006] U.S. Patent No. 7,141,698 has also reported the continuous synthesis method of pseudomethyl ionone and methyl ionone, but it adopts a large amount of alkali catalyst, also needs to utilize acetic acid to neutralize, waste a large amount of alkali on the one hand, also cause a large amount of on the other hand The three wastes

Method used

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  • A kind of preparation method of methyl ionone and intermediate thereof
  • A kind of preparation method of methyl ionone and intermediate thereof

Examples

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Embodiment 1

[0031] In a three-necked flask with a stirring device, a thermometer and a dropping funnel, add 200g of PEG-600 and 11g of potassium hydroxide. After the dissolution is complete, add 100g of butanone, and mix the mixture of 50g of citral and 20g of butanone under stirring. Add dropwise into the reaction system for 1 hour, and the dropwise reaction temperature is 10°C. After the dropwise addition, raise the temperature to 20°C and continue the heat preservation reaction for 1 hour. Once, the n-hexane layers were combined, washed with water, washed with saturated brine, evaporated by rotary evaporation to remove the solvent, and then distilled under reduced pressure to collect fractions at 140Pa / 115-118°C to obtain a pseudomethyl ionone product with a purity of 99% and a yield of 94 %, the proportion of pseudo-isomethyl ionone is 75%.

Embodiment 2

[0033] In a three-necked flask with a stirring device, a thermometer and a dropping funnel, add 200g of PEG-200 and 11g of potassium hydroxide. After the dissolution is complete, add 100g of butanone, and mix the mixture of 50g of citral and 20g of butanone under stirring. Add dropwise into the reaction system for 1 hour, and the dropwise reaction temperature is 10°C. After the dropwise addition, raise the temperature to 20°C and continue the heat preservation reaction for 1 hour. Once, the n-hexane layers were combined, washed with water, washed with saturated brine, evaporated to remove the solvent, and distilled under reduced pressure to collect fractions at 140Pa / 115-118°C to obtain a pseudomethyl ionone product with a purity of 99% and a yield of 92 %, the proportion of pseudo-isomethyl ionone is 73%.

Embodiment 3

[0035]In a three-necked flask with a stirring device, a thermometer and a dropping funnel, add 200g of PEG-400 and 11g of potassium hydroxide. After the dissolution is complete, add 100g of butanone, and mix the mixture of 50g of citral and 20g of butanone under stirring. Add dropwise into the reaction system for 1 hour, and the dropwise reaction temperature is 10°C. After the dropwise addition, raise the temperature to 20°C and continue the heat preservation reaction for 1 hour. Once, the n-hexane layers were combined, washed with water, washed with saturated saline, evaporated to remove the solvent, and distilled under reduced pressure to collect fractions at 140Pa / 115-118°C to obtain a pseudomethyl ionone product with a purity of 99% and a yield of 93 %, the proportion of pseudo-isomethyl ionone is 76%.

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Abstract

The invention discloses methylionone and a preparation method of a methylionone intermediate. According to an existing preparation method of methylionone, a lot of alkali usually needs to be wasted, and on the other hand, a lot of three wastes are caused. Under the conditions that citral and butanone serve as raw materials, PEG serves as a solvent and metal hydroxide serves as a condensation agent, an Aldol condensation reaction is conducted, and false methylionone is synthesized; the obtained false methylionone is subjected to a cyclization reaction catalyzed by acid, and methylionone is synthesized. According to methylionone and the preparation method of the methylionone intermediate, an adopted PEG-M(OH)x catalysis system improves the synthesis efficiency of the false methylionone, and the ratio of the false methylionone is kept at 68-79%; moreover, an adopted phosphoric acid-normal hexane catalytic cyclization system greatly improves the cyclization yield; an adopted catalytic condensation system can be used indiscriminately for several times, so that the cost is reduced, and environmental pollution is also reduced.

Description

technical field [0001] The invention belongs to the fields of fragrance chemistry and fine chemicals, and in particular relates to a preparation method of methyl ionone and its intermediate. Background technique [0002] Methyl ionone is a very precious synthetic fragrance, which has six isomers, including cis and trans isomers and optical isomers, which exist in synthetic products as a mixture, usually with the most typical aroma The characteristic α-isomethyl ionone (α-IMI) isomer accounts for more than 60% of the main component. Synthetic products are usually pale yellow to yellow liquid with a soft violet aroma, used to prepare a variety of essences, especially essences and perfumes such as violet type and lily type. [0003] Methyl ionone is usually prepared by cyclization after condensation of citral (Citral) and methyl ethyl ketone (MEK). Its preparation method is similar to that of β-ionone, but far more complicated than that of β-ionone. CH 3 and CH at position 3...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/74C07C49/203C07C45/67C07C49/21
CPCC07C45/67C07C45/74C07C49/203C07C49/21
Inventor 张玉红肖唐鑫胡柏剡于明张龙徐铭孙恒涛朱勋苏雅静朱先冬求渭川李其川陈志荣李浩然
Owner ZHEJIANG NHU CO LTD
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