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Preparation method of di(dibenzalacetone)palladium(0)

A technology of dibenzylideneacetone and acetone is applied in the field of preparation of bis(dibenzylideneacetone)palladium(0), and can solve the problems of long reaction time, difficult operation, and not strictly controlling the amount of ligand added.

Active Publication Date: 2011-04-13
JINCHUAN GROUP LIMITED
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  • Abstract
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Problems solved by technology

The shortcoming of these methods is: (1) in the preparation process of sodium tetrachloropalladate, can introduce excessive equally water-soluble sodium chloride, be difficult to obtain pure sodium tetrachloropalladate; (2) adopt methyl alcohol as reaction solvent, The environment is not friendly; (3) The reaction is carried out at low temperature, the reaction time is long, and the required equipment is complicated; (4) The process of adding raw materials is cumbersome, and it is difficult to operate under anhydrous and oxygen-free conditions; (5) Due to the presence of Equilibrium between bis(dibenzylideneacetone)palladium(0) and tris(dibenzylideneacetone)palladium(0) and tris(dibenzylideneacetone)palladium(0), literature does not strictly control ligands The amount added, the product obtained is a mixture

Method used

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preparation example Construction

[0015] A kind of preparation method of two (dibenzylideneacetone) palladium (0), the step of preparation process comprises:

[0016] (i) Preparation of palladium dichloride: take a certain amount of palladium sponge, mix and dissolve with hydrochloric acid of 32% concentration and hydrogen peroxide of 30% concentration, lower the temperature of the electric heating plate, and slowly evaporate the obtained chloropalladium acid solution by dissolving Dry to get palladium dichloride;

[0017] (ii) Synthesis of dibenzylideneacetone: Measure a certain volume of 95% ethanol, 100g / L sodium hydroxide solution, and deionized water in a 50L circular glass reactor, and add a certain amount of benzaldehyde in turn under stirring , acetone, control the reaction temperature at 20-40°C, and continue the reaction for 2 hours to form a light yellow precipitate;

[0018] (Ⅲ) the suspension in step (ii) is cooled to room temperature, and is vacuum filtered to obtain the thick product of dibenzy...

Embodiment 1

[0022] Preparation of dibenzylidene acetone: Weigh 600g of sodium hydroxide, dissolve it with 6L of deionized water and add it to a 50L round glass reactor, then add 12L of deionized water, 12L of 95% ethanol, 1.59L of benzaldehyde, and 540ml of acetone ; Stir mechanically, react at room temperature for 2h; filter with suction, recrystallize from absolute ethanol, dry and weigh to obtain 1421.5g of product, yield 81%;

[0023] Product preparation: take 120g palladium sponge, mix and dissolve with 32% hydrochloric acid and 30% hydrogen peroxide, slowly evaporate the resulting solution to dryness to obtain palladium dichloride; mix palladium dichloride, 884.62g dibenzyl Diethyl acetone (prepared for use in advance), 750.00g of anhydrous sodium acetate, and 24L of anhydrous ethanol were added to the jacketed reactor, and the oil bath was heated to 65°C. Continue to react at 45°C for 2 hours, cool to room temperature, filter with suction, wash with absolute ethanol, deionized wate...

Embodiment 2

[0025] The specific implementation rules are the same as in Example 1, except that the sponge palladium is 240g, the dibenzylidene acetone is 1769.24g, anhydrous sodium acetate 1500.00g, and absolute ethanol 30L; the oil bath is reacted at 65°C for 30min, and at 45°C for 2h; The rate is 90.9%; the elemental analysis results are C: 70.65%, H: 4.87%, Pd: 18.21%.

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Abstract

A preparation method of di(dibenzalacetone)palladium(0) relates to a preparation method of a zerovalent palladium catalyst, namely di(dibenzalacetone)palladium(0) which is used in the catalytic hydrogenation, coupling, carbonylation, cyclotrimerization of alkynes and other aspects of the organic synthesis. The invention is characterized in that the preparation process is as follows: under nitrogen atmosphere, palladium dichloride and ligand dibenzalacetone are stirred to react in absolute alcohol, suction filtering is performed, absolute alcohol, water and acetone are used for cleaning, and finally the product can be obtained through drying. In the preparation method in the invention, palladium dichloride, dibenzalacetone and anhydrous sodium acetate are fed at once to synthetize di(dibenzalacetone)palladium(0) in absolute alcohol solvent through one pot method; and the key point of the technology is as follows: the molar ratio of palladium dichloride and dibenzalacetone is strictly controlled so as to obtain the pure di(dibenzalacetone)palladium(0) product. By adopting the method in the invention, the production technology can be effectively simplified and the method is environment-friendly.

Description

technical field [0001] A preparation method of bis(dibenzylideneacetone) palladium (0), relating to a zero-valent palladium catalyst used in catalytic hydrogenation, coupling, carbonylation, alkyne ring trimerization, etc. in organic synthesis, Process for the preparation of bis(dibenzylideneacetone)palladium(0). Background technique [0002] As the most important zero-valent palladium catalyst, bis(dibenzylideneacetone)palladium(0) is widely used in catalytic hydrogenation, coupling, carbonylation, and alkyne cyclotrimerization. For example, palladium catalyzes the Negishi reaction of halogenated hydrocarbons and organozinc, the Stille reaction of halogenated hydrocarbons and organotin, the Suzuki reaction of halogenated hydrocarbons and organoboron, the Heck reaction of halogenated hydrocarbons and olefins, etc. These reactions are important in the synthesis of natural products. , polymers, functional materials, liquid crystal materials, and bioactive compounds and drugs ...

Claims

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Application Information

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IPC IPC(8): C07F15/00
Inventor 易镇芳林阳辉张静郭守杰马正明马骞王艳艳刘国旗辛冰冯燕王红梅高新涛吕美
Owner JINCHUAN GROUP LIMITED
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