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Method for preparing oxo-isophorone by catalytic oxidation using metal free catalytic system

A technology for oxoisophorone and isophorone, which is applied in the field of catalyzed synthesis of oxoisophorone by a metal-free catalytic system, can solve the problems of harsh reaction conditions, corrosion, and unsatisfactory effects, and achieves high selectivity. , mild conditions

Inactive Publication Date: 2009-04-29
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Commonly used catalysts are mainly concentrated on transition metal compounds, but α-isophorone is relatively stable and difficult to be oxidized, so the catalytic effect is not ideal, the general reaction conditions are relatively harsh, and the selectivity of KIP is low
In addition, the use of metals as catalysts has problems such as large environmental pollution and corrosive effects on industrial equipment.

Method used

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  • Method for preparing oxo-isophorone by catalytic oxidation using metal free catalytic system
  • Method for preparing oxo-isophorone by catalytic oxidation using metal free catalytic system
  • Method for preparing oxo-isophorone by catalytic oxidation using metal free catalytic system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Add 3.26g of N-hydroxyphthalimide catalyst and 100ml of acetonitrile into a 250ml round-bottomed three-neck flask, put it in a water bath at 40°C, and then add 2.76g of α-isophorone after 20 minutes. 0.02g of benzoyl peroxide, then feed oxygen to react, the reaction process is monitored by gas chromatography, and ethyl benzoate is used as internal standard to calibrate, after 36h, the conversion rate of α-isophorone is measured to be 50% , the selectivity of oxyisophorone was 91%.

Embodiment 2-3

[0018] Similar to Example 1, the main catalyst was changed, the reaction temperature was carried out under the condition of 55°C, the reaction time was 24h, and the following results were obtained after the reaction (Table 1):

[0019] Table 1 The influence of the change of the main catalyst on the catalytic effect of a-isophorone

[0020]

[0021] Example 4-6

[0022] Similar to Example 1, the co-catalyst was changed, the reaction temperature was carried out under the condition of 60°C, the reaction time was 24h, and the following results were obtained after the reaction (Table 2):

[0023] Table 2 The influence of the change of co-catalyst on the catalytic effect of a-isophorone

[0024]

Embodiment 7-10

[0026] Similar to Example 1, the solvent was changed, the reaction temperature was 50°C, the reaction time was 24h, and the following results were obtained after the reaction (Table 2):

[0027] The influence of the change of table two solvents on the catalytic effect of a-isophorone

[0028]

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Abstract

The invention relates to a method for preparing keto-isophorone by the catalytic oxidation of a metal free co-catalyst system, which is characterized in that, Alpha-isophorone is used as the raw material; in the presence of an organic solvent, oxygen or an oxygen rich gas is used as an oxidant; under the effect of the co-catalyst system composed by the main catalyst N-hydroxyphthalimide and the analogues of N-hydroxyphthalimide, and organic cocatalyst, keto-isophorone is prepared by catalytic oxidation; reaction temperature ranges from 10 to 100 DEG C; reaction time ranges from 1 to 70 hours; keto-isophorone with high selectivity can be generated. The method has the advantages that, the catalyst is metal free, cheap and easy to be obtained; reaction conditions are mild; operation is simple; the product has high selectively and other advantages.

Description

technical field [0001] The invention relates to a method for preparing oxoisophorone through oxidation reaction by using alpha-isophorone as a raw material under the catalytic action of a metal-free catalytic system. Background technique [0002] Oxyisophorone, referred to as KIP, oxyisophorone can not only be used as a seasoning or fragrance in food or cosmetic preparations, but also an intermediate for the preparation of various carotenoids, vitamins and fragrances. It is a light yellow liquid or solid at room temperature. Its pure product has a strong aroma and long-lasting aroma. The aroma is slightly sour, densely sweet, woody, and dried fruit. Ketoisophorone is a natural product that can be directly extracted from plants, but this not only requires a large amount of raw materials, but also has a very low yield. Therefore, since the 1970s, artificially synthesized ketoisophorone Ketone has been widely concerned at home and abroad. [0003] Because KIP has a wide range...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/603C07C45/34
Inventor 李浩然陈志荣王国梁胡兴邦王从敏胡柏剡
Owner ZHEJIANG UNIV
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