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Preparation method of ruthenium-carbene catalyst

A carbene catalyst and halide technology, which is applied in the field of preparation of ruthenium carbene catalysts, can solve the problems of low reaction temperature, long reaction time, low product yield, unsuitable for industrialized implementation, etc., and achieve high product yield and good product purity.

Active Publication Date: 2017-10-10
CHINA PETROLEUM & CHEM CORP +1
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Problems solved by technology

[0013] The purpose of the present invention is to provide a kind of preparation method of ruthenium carbene catalyst in order to overcome the problem that reaction temperature is too low or reaction time is too long in the method for producing ruthenium carbene catalyst in the prior art, and product yield is low and is not suitable for industrialized implementation

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  • Preparation method of ruthenium-carbene catalyst
  • Preparation method of ruthenium-carbene catalyst
  • Preparation method of ruthenium-carbene catalyst

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preparation example Construction

[0020] The invention provides a method for preparing a ruthenium carbene catalyst, the method comprising: (1) under the protection of an inert gas and in the presence of an organic solvent, at a temperature of -20°C to 0°C, diazobenzyl and dihalogenated tetrakis( Triphenylphosphine) ruthenium is subjected to the first reaction for 15-60min; (2) under the protection of an inert gas, the reaction product obtained in step (1) is subjected to the second reaction with tricyclohexylphosphine to obtain two-tricyclohexylphosphine- Phenylidene-dichlororuthenium complex.

[0021] In the present invention, the chemical formula of dihalogenated tetrakis (triphenylphosphine) ruthenium is RuX 2 (PPh 3 ) 4 (Ph represents phenyl), X=Cl, Br or I, preferably Cl. The chemical formula of diazobenzyl is PhCHN 2 , the structural formula is

[0022] According to a preferred embodiment of the present invention, in step (1), the molar ratio of diazobenzyl to dihalogenated tetrakis(triphenylphos...

Embodiment approach

[0049] According to a preferred embodiment of the present invention, the mol ratio of benzaldehyde-p-toluenesulfonylhydrazone to the base is 1:(2~8); triethylene glycol and benzaldehyde-p-toluenesulfonate The molar ratio of acylhydrazone is (50-100):1, preferably the molar ratio of triethylene glycol to benzaldehyde-p-toluenesulfonylhydrazone is (63-94):1.

[0050] According to the present invention, preferably, the base is at least one of sodium methoxide, sodium ethoxide and sodium tert-butoxide.

[0051] A kind of preferred embodiment of the present invention, as mentioned above, the concrete process that obtains the organic solution that contains diazonium benzyl can be: benzaldehyde-p-toluenesulfonyl hydrazone, alkali and triethylene glycol are mixed, then Carry out the second synthesis at a reaction temperature of 40° C. to 80° C. for 1 to 2 hours, and remove the alcohol generated by the second synthesis by vacuuming in the middle. After the second synthesis, all the ma...

Embodiment 1

[0063] This example illustrates the preparation method of the ruthenium carbene catalyst of the present invention.

[0064] (1) Synthesis of dichloro tetrakis (triphenylphosphine) ruthenium

[0065] 0.6g (2.2mmol) of trihydrate ruthenium trichloride (RuCl 3 ·3H 2 (0, commercially available from Bailingwei) was dissolved in 150ml methanol and filtered to obtain a methanol solution of ruthenium trichloride trihydrate and the solution was refluxed for 5min under nitrogen protection, then the solution was cooled to 0°C; 3.6g (13.7mmol) Triphenylphosphine (P(Ph) 3 , commercially available from Bailingwei) was added to the above-mentioned cooled solution for the first synthesis, and a dark brown product solution was obtained. The product solution was stirred at about 25° C. under a nitrogen atmosphere for 24 hours, and then dark brown was collected under nitrogen protection. Crystallization product, this crystallization product is washed with the methanol of degassing, ether, and...

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Abstract

The invention relates to the field of preparation of ruthenium-carbene catalysts, and discloses a preparation method of a ruthenium-carbene catalyst. The method comprises the following steps: (1) in the presence of an inert gas protective atmosphere and an organic solvent, performing a primary reaction on diazobenzyl and dihalotetra(triphenylphosphine)ruthenium at -20 DEG C to 0 DEG C for 15-60 minutes; and (2) in an inert gas protective atmosphere, performing a secondary reaction on the reaction product obtained in the step (1) and tricyclohexyl phosphine to obtain the di-tricyclohexyl phosphine-phenylethylene-dichlororuthenium complex. The method can be utilized to obtain the ruthenium-carbene catalyst at higher temperature within a shorter time at higher product yield, and is more suitable for implementing industrial production.

Description

technical field [0001] The invention relates to the field of preparation of ruthenium carbene catalysts, in particular to a preparation method of ruthenium carbene catalysts. Background technique [0002] Olefin metathesis is a process in which two broken olefin carbon-carbon double bonds are recombined into new carbon-carbon double bonds. It is widely used in the synthesis of natural products and materials science. [0003] The factor that has the greatest influence on the olefin metathesis reaction is the catalyst. Over the years, the search for efficient and specific catalysts has been the research focus of olefin metathesis. Schrock, Grubbs, and Chauvin jointly won the 2005 Nobel Prize in Chemistry for their contributions to olefin metathesis catalysts. [0004] In the olefin metathesis catalyst system, the most widely used and most practical is the Grubbs catalyst (Grubbs catalyst, a ruthenium carbene complex catalyst). At present, the catalyst has experienced nearl...

Claims

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Application Information

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IPC IPC(8): B01J31/24C07F15/00
CPCB01J31/2404B01J2531/821C07F15/0046
Inventor 包蒙梁爱民邵明波毕海鹏徐林赵姜维
Owner CHINA PETROLEUM & CHEM CORP
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