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Preparation of loaded Grubbs catalyst and application of loaded Grubbs catalyst

A catalyst and supported technology, which is applied in the field of chemical catalytic materials and chemical applications, can solve the problems of reduced catalytic activity, and achieve the effects of simplified post-processing, good catalytic activity, and convenient preparation

Inactive Publication Date: 2012-08-08
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There have been reports in the literature on Grubbs-type catalyst loading, and the loaded materials include polystyrene, vinyl polystyrene, polyethylene glycol, polyethylene adipate, fluorine-containing polyacrylate, and monolithic sols. - Gel materials and ionic liquids, etc., but these supported catalysts either reduce their catalytic activity quickly after recovery, or need to use mixed solvents in the reaction, or the catalyst needs to be recovered through complicated operations after the reaction, which limits the supported Grubbs Application of Catalysts in Industrial Production

Method used

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  • Preparation of loaded Grubbs catalyst and application of loaded Grubbs catalyst
  • Preparation of loaded Grubbs catalyst and application of loaded Grubbs catalyst

Examples

Experimental program
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Effect test

Embodiment 1

[0027] a. Preparation of aminated mesoporous materials

[0028] Vacuumize the SBA-15 mesoporous material at 90°C for 4 hours and cool to room temperature, then take 2.5g of SBA-15 inorganic mesoporous material and mix it with 43ml of anhydrous toluene under the protection of argon, then add 1.25g of 3-amino Propyltriethoxysilane, then heated to 110°C under reflux and stirred for 24 hours, filtered after the reaction, the filtrate was washed with 30ml of toluene, 30ml of ethanol and 30ml of acetone, collected, and dried in vacuo to obtain light yellow solid amino FeSBA-15 mesoporous material 2.8g, its 3-aminopropyltriethoxysilane, ethanol and acetone are chemically pure.

[0029] b. Preparation of amidated mesoporous materials

[0030] At room temperature and under argon protection, mix 1.0g 3-3-vinyl-4-isopropoxyphenyl-propionic acid with 0.98g dicyclohexylcarbodiimide, 0.16g 4-dimethylaminopyridine, 0.075 g of p-toluenesulfonic acid and 48ml of N,N-dimethylformamide were mi...

Embodiment 2

[0037] a. Preparation of aminated mesoporous materials

[0038] at -5 o C and under argon protection, mix 2.5g FDU-14 mesoporous material with 12ml chloromethyl ether, add 3.0g anhydrous aluminum trichloride in three batches, stir at room temperature for 12 hours, then cool the reaction mixture to 0 o After C, filter, and the filtrate is washed successively with 30 parts by weight of water and 10 parts by weight of acetone and collected, and after vacuum drying, the brown solid is chlorinated FDU-14 mesoporous material, and its chloromethyl ether, anhydrous aluminum trichloride and acetone are chemically pure;

[0039] At room temperature and under the protection of argon, mix 2.5g of the above-prepared chlorinated FDU-14 mesoporous material with 12ml of anhydrous ethylenediamine, stir at 80°C for 24 hours, filter after the reaction, and use the filtrate in turn After washing with 100ml of water and 50ml of acetone, it was collected and dried in vacuo to obtain a brown soli...

Embodiment 3

[0048] The specific application of SBA-15 first-generation supported Grubbs catalyst for N, N-diallyl-4-methylbenzenesulfonamide catalyzed ring-closing olefin metathesis reaction (RCM) will be further described in detail for the present invention :

[0049] Under the protection of argon, 0.36 g of the first-generation supported Grubbs catalyst of SBA-15 mesoporous material supported phenylmethylene-bistricyclohexylphosphine-ruthenium dichloride was mixed with N in a dry reaction tube. , N-diallyl-4-methylbenzenesulfonamide 0.2g and dichloromethane 4ml mixed, stirred and heated to 38 o C, TLC monitoring to the end of the reaction, then suction filtration, the filtrate was concentrated and column chromatography to obtain a white solid 2,5-dihydro-1-p-toluenesulfonylpyrrole, the yield was 98%, filtered out The catalyst was collected after being washed three times with 8ml of dichloromethane, and the catalyst was recovered for recycling. N, N-diallyl-4-methylbenzenesulfonamide wa...

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Abstract

The invention discloses preparation of a loaded Grubbs catalyst and application of loaded Grubbs catalyst. The preparation is characterized in that: the catalyst is obtained by using the compound obtained by the amidation reaction of 3-3-ethenyl-4-isopropoxyphenyl-propionic acid as a loading precursor and then enabling the compound to carry out exchange complexation respectively with phenyl methylene-bistricyclohexylphosphine-dichlororuthenium or 1, 3-bis 2, 4, 6-trimethylphenyl-2-imidazolidinylidene-dichorobenzenemethylene-tricyclohexylphosphineruthenium; the catalyst is used for the olefinmetathesis reaction of N,N-diallyl-4-methylbenzenesulfonamide and has quite strong catalytic activity. Compared with the prior art, the catalyst of the invention is simple in process and convenient in preparation, and can be recycled many times and keep excellent catalytic activity, thereby greatly reducing the heavy metal pollution caused by Grubbs type catalysts to the product of olefin metathesis reaction and developing a new way for green and environmentally-friendly organic synthetic chemistry.

Description

technical field [0001] The invention relates to the technical field of chemical catalytic materials and chemical applications, in particular to the preparation and application of a loaded Grubbs catalyst used for recycling in heterogeneous catalyzed olefin metathesis reactions. Background technique [0002] Since the 1950s, olefin metathesis reactions have attracted extensive research. Olefin metathesis is a unique carbon skeleton rearrangement reaction, which refers to the process of cutting and recombining carbon-carbon double bonds under metal catalysis, which makes the double and triple bonds that are chemically inert in the usual sense Coupled with each other, they are widely valued by academia and industry. [0003] In the past few decades, the developed olefin metathesis catalysts are all multi-component catalysts, such as MoO 3 / SiO 2 , Re 2 o 7 / A1 2 o 3 ,WC1 6 / Bu 4 Sn et al. However, since these catalytic systems usually require harsh reaction conditio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07D207/48
CPCY02P20/50
Inventor 吴海虹张焕刘月明吴鹏
Owner EAST CHINA NORMAL UNIV
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