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Epoxide generation method by catalytic oxidation of functionalized alkene

A technology of epoxide and oxidation function, which is applied in the direction of organic chemical methods, chemical instruments and methods, organic oxidation, etc., can solve the problems of high price of peroxyacid, low conversion rate of raw materials, long reaction time, etc., and achieve low cost, High reaction efficiency and short reaction time

Inactive Publication Date: 2005-06-29
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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Problems solved by technology

Among them, sodium hypochlorite, peroxyacid and alkyl hydroperoxide generally have disadvantages such as poor stability and easy decomposition, and peroxyacid itself is expensive, and the difficulties encountered in safe production have been gradually replaced by new epoxidized Trends in reagent substitution
Although hydrogen peroxide and oxygen are from the application point of view, molecular oxygen is a cheap, convenient and clean oxygen source, but its activity is low, and there are long reaction times and raw material conversion in the preparation of α, β-epoxy carbonyl compounds. The disadvantages of low efficiency, low efficiency, difficult operation and high cost

Method used

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  • Epoxide generation method by catalytic oxidation of functionalized alkene
  • Epoxide generation method by catalytic oxidation of functionalized alkene

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Experimental program
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Effect test

Embodiment 1

[0027] Preparation of solid base: Dissolve 58 grams of potassium fluoride in 100 grams of water, add 100 grams of neutral alumina (for chromatography, 100-200 mesh), stir and react at 60°C for 1 hour, then heat up and evaporate the water to dryness, solid The product was dried at 120°C for 4 hours to obtain the solid base KF / Al 2 o 3 , placed in a desiccator for later use.

Embodiment 2

[0029] In a 250ml three-necked flask, add 25mL of N,N-dimethylformamide, 2.325 grams (10mmol) of trichloroisocyanuric acid, 2.0 grams of KF / Al 2 o 3 , after stirring for 15min, add chalcone (i.e. R in the structure (I) 1 ~R 10 hydrogen) 2.08 grams (10mmol), stirred at room temperature for 10min, filtered to remove KF / Al 2 o 3 Solid, most of the solvent was evaporated under reduced pressure, then water (10 mL) was added to the residue, and extracted with dichloromethane (2 × 20 mL) (note: the extracted water can be used in the next batch of reactions, without affecting the yield and purity of the reaction). After the extract was dried over anhydrous sodium sulfate, the solvent was evaporated to obtain an epoxidized product, which was recrystallized, dried, and weighed to obtain 2.021 grams, with a yield of 90.1% (calculated as olefins), and an HPLC analysis purity of 99%. above. The content determination adopts Waters high-performance liquid chromatography system, includi...

Embodiment 3

[0031] The organic solvent used is a mixture of benzene and N,N-dimethylformamide. The test method and steps are the same as in Example 2. The reaction time is 30 minutes, the yield is 78.2%, and the HPLC analysis purity is above 99%.

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Abstract

The invention relates to the chemical reaction course of multi-phase catalysis and oxidation for preparing epoxide, concretely, a method for generating epoxide by catalysis and oxidation and functionalization for alkene. Use inedible in organic solvent as epoxidinf agent, potassium fluoride carried on alumina as solid alkali, catalyze alkene to generate epoxide in the temperature of 0~80deg.C for 0.1~20h. Its advantages include: high conversion rate of raw material, good selectivity of target products, short time for reaction high efficiency, friendly condition for reaction, low cost, can be easily controlled, and no pollution to the environment.

Description

technical field [0001] The invention relates to a chemical reaction process for preparing epoxides through heterogeneous catalytic oxidation, in particular to a method for catalytically oxidizing functionalized olefins to generate epoxides. Background technique [0002] Epoxy compounds are not only an important class of organic synthesis intermediates [Document 1: Tetrahedron: Asymmetry, 2001, 12, 2359-2383, etc.], they are widely used in petrochemical, fine chemical and organic synthesis fields, and have certain Epoxy compounds with special structures are widely distributed in natural products and organisms, and are structural units with important physiological activities in organisms, such as galacturonic acid derivatives [Document 2: J.Chem.Soc., Perkin Trans .1 2001, 149-153. etc.], protein kinase C agonist [Document 3: Tetrahedron Lett.2000, 41, 9569-9574, etc.]. Therefore, how to efficiently synthesize such compounds under mild conditions has always been the goal purs...

Claims

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Application Information

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IPC IPC(8): C07B33/00C07B37/10C07D301/03
Inventor 张国富叶金星王永灿梁鑫淼陈吉平
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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