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Dioxime ionone as well as preparation method and application thereof

A technology of ionone and ionone molarity, applied in oxime preparation, hydrolysis preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of low process yield, low yield, difficult vacuum distillation or recrystallization, etc. The effect of simple route, simple operation and low cost

Inactive Publication Date: 2015-04-01
SHAOXING UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, it is also an important intermediate for the artificial synthesis of carotenoids. It is widely used in the pharmaceutical industry and has a good application prospect; but the current artificial synthesis method has not yet achieved industrial production.
Among the many synthetic methods reported, the chromium salt oxidation method pollutes the environment; the sodium chlorate oxidation method conditions are not suitable for control; the electrolytic oxidation method has many by-products, low yield, and high energy consumption; the molecular oxygen catalytic oxidation method is the most environmentally friendly and effective Promising, but the existing process has low yield and difficult purification
Due to the fact that the raw materials, products and by-products of existing oxidation methods are all high-boiling substances with close boiling points and little difference in polarity, it is difficult to vacuum rectify or recrystallize. Therefore, column chromatography is generally used for separation and purification in literature reports, and it is difficult to realize industrial production

Method used

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  • Dioxime ionone as well as preparation method and application thereof
  • Dioxime ionone as well as preparation method and application thereof
  • Dioxime ionone as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of dioxime-ionone (1)

[0031] Add 96g (0.5mol) β-ionone, 9g (0.05mol) NHPI and 1.3g (5.0mmol) cobalt acetylacetonate successively in a 250mL four-neck flask, stir mechanically, and pass oxygen at 60°C. Gas chromatography followed and detected the reaction until the raw material content was less than 5%. The above reaction solution was cooled to room temperature, transferred to a 1000mL four-neck flask, added 500mL of 50% (volume ratio) ethanol aqueous solution, 69.5g (1mol) of hydroxylamine hydrochloride and 82g sodium acetate (1mol), and refluxed for 2 hours. Cool down, evaporate the solvent to dryness, add 400mL dichloromethane and 250mL water to the residue, stir for half an hour, separate layers, evaporate the solvent in the lower dichloromethane layer, recrystallize with 300mL ethyl acetate, filter and dry to obtain a white powder The solid is 60.5g, the liquid chromatography content is 99.2%, the yield is 51.1%, and the melting point is 21...

Embodiment 2～8

[0038] Examples 2-8: Preparation of dioxime-ionone (1) under different bases, solvents and temperature conditions

[0039] Add 9.6g (50mmol) β-ionone, 0.9g (5.0mmol) NHPI and 0.13g (0.50mmol) cobalt acetylacetonate successively into a 100mL four-neck flask, stir mechanically, and pass oxygen at 60°C. Gas chromatography followed and detected the reaction until the raw material content was less than 5%. The above reaction solution was cooled to room temperature, transferred to a 500mL four-neck flask, added 50mL alcoholic aqueous solution, hydroxylamine hydrochloride and alkali, and refluxed for 2 hours. Cool down, evaporate the solvent to dryness, add 40mL dichloromethane to the residue

[0040] Alkanes and 25mL water, stirred for half an hour, separated into layers, evaporated the solvent in the lower methylene chloride layer, recrystallized from ethyl acetate, filtered, dried and weighed, measured the content of the liquid phase, and calculated the yield.

[0041] The resul...

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PUM

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Abstract

The invention discloses dioxime ionone as well as a preparation method and application thereof, and belongs to the technical field of preparation of pharmaceutical and chemical intermediate products. Dioxime ionone is characterized by being prepared by the steps of oxidizing beta-ionone through oxygen with presence of a catalyst, and implementing an oximation reaction with hydroxylamine hydrochloride to obtain dioxime ionone. The prepared dioxime ionone disclosed by the invention is shown in formula I in the specification, and contains oximido and multi-conjugated double bonds as well as an unique Zhi-ring structure; the dioxime ionone can be further hydrolyzed with presence of an acid to prepare 4-oxo-beta-ionone which is relatively high in purity; therefore, the dioxime ionone has a quite high industrial value.

Description

Technical field: [0001] The invention relates to a pharmaceutical and chemical intermediate, in particular to a dioxime-ionone and its preparation method and application. Background technique: [0002] 4-Oxo-β-ionone is an important synthetic spice and an important intermediate in the production of pharmaceuticals, spices, food additives, agricultural chemicals, etc. In cigarettes, the amount of tar and nicotine can be reduced, the flavor can be supplemented, and the quality of smoke can be improved to achieve a significant flavoring effect. At the same time, it is also an important intermediate for the artificial synthesis of carotenoids. It is widely used in the pharmaceutical industry and has a good application prospect; but the current artificial synthesis method has not yet achieved industrial production. Among the many synthetic methods reported, the chromium salt oxidation method pollutes the environment; the sodium chlorate oxidation method conditions are not suitab...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C249/08C07C251/44C07C45/42C07C49/647
Inventor 沈润溥宋小华张符吴春雷盛国栋陈斌李春晶严共高
Owner SHAOXING UNIVERSITY
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