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Preparation method and application of catalyst

A catalyst and solvent technology, applied in the field of preparation of Salen organic polymers and Co catalysts, can solve the problems of difficult recovery and cannot be reused, and achieve the effects of easy recovery, good effect, and maintaining catalytic activity.

Inactive Publication Date: 2017-04-19
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The problem to be solved by the present invention is to overcome the defects that traditional metal Salen catalysts are not easy to recycle and cannot be reused, and a method is provided to prepare Salen organic polymers with mesoporous structure characteristics, and then to prepare a reproducible The heterogeneous Co catalyst used, which can be used for the catalytic oxidation of benzoin to obtain benzil

Method used

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  • Preparation method and application of catalyst
  • Preparation method and application of catalyst
  • Preparation method and application of catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057]

[0058] In a 250 mL round bottom flask, add salicylaldehyde (21.2 mL, 200 mmol), potassium carbonate (41.4 g, 300 mmol), DMF (100 mL), and magneton in sequence. With stirring at room temperature, allyl bromide (20.74 mL, 240 mmol) was slowly added dropwise, and reacted at room temperature for more than 12 hours, and was detected by TLC analysis until the reaction was complete. After the reaction was complete, ethyl acetate and water were added to the reaction solution for extraction. The organic phase was first washed 3 times with water to remove DMF, and then washed once with saturated brine. The obtained organic phase was washed with anhydrous Na 2 SO 4 Dry, filter and concentrate under reduced pressure to obtain the product which is phenyl allyl ether.

[0059] structure of the product 1 H-NMR and 13 C-NMR determines that its data are as follows:

[0060] 1 H-NMR (400MHz, CDCl 3 )δppm 7.77(dd, J=7.6,1.6Hz,1H),7.48-7.44(m,1H),6.96(dd,J=8.0,8.0Hz,1H),6.91(d,J...

Embodiment 2

[0063]

[0064] In a 100mL round-bottomed flask, add phenyl allyl ether (1.026g) obtained in Example 1 and magnetons, and heat the round-bottomed flask in an oil bath at 200°C after connecting a condenser to cause Claisen rearrangement reaction . After reacting for 4 hours, the reaction was complete according to TLC analysis, and the yellow oily liquid formed was the Claisen rearrangement reaction product.

[0065] structure of the product 1 H-NMR and 13 C-NMR determines that its data are as follows:

[0066] 1 H-NMR (400MHz, CDCl 3 )δppm 11.3(s, 1H), 9.89(s, 1H), 7.44(d, J=7.6Hz, 1H), 7.42(d, J=7.6Hz, 1H), 6.98(dd, J=7.6, 7.6Hz ,1H),6.06-5.95(m,1H),5.14-5.11(m,1H),5.09-5.08(m,1H),3.45(m,1H),3.44(m,1H);

[0067] 13 C-NMR (100MHz, CDCl 3 ) δppm 196.7, 159.5, 137.1, 135.8, 131.9, 128.8, 120.3, 119.6, 116.2, 33.0.

Embodiment 3

[0069]

[0070] In a 250 mL round bottom flask, add Claisen rearrangement product (1.6 mL, 0.018 mol), ethylenediamine (0.5 mL, 0.0075 mol), ethanol (50 mL) in sequence, and heat and stir in a 75°C water bath for 5 hours. After the reaction solution was cooled to room temperature, ethyl acetate and water were added, the organic phase was washed 3 times with water, and then once with saturated brine, and the obtained organic phase was washed with anhydrous Na 2 SO 4 Drying, filtration and concentration under reduced pressure afforded the product Salen.

[0071] The structure of the product Salen is used 1 H-NMR and 13 C-NMR determines that its data are as follows:

[0072] 1 H-NMR (400MHz, CDCl 3 )δppm 13.6(s, 1H), 8.37(s, 1H), 7.21(d, J=7.2Hz, 1H), 7.14(d, J=7.6Hz, 1H), 6.84(dd, J=7.6, 7.2Hz ,1H),6.11-6.01(m,1H),5.12(d,J=11.2Hz,1H),5.09(s,1H);

[0073] 13 C-NMR (100MHz, CDCl 3 )δppm 166.7(×2), 158.9(×2), 136.6(×2), 132.7(×2), 129.7(×2), 127.8(×2), 118.4(×2), 118.2(...

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Abstract

The invention discloses a preparation method and application of a catalyst. The preparation method of the catalyst is characterized by comprising the following steps that (1) in a polar aprotic solvent solution, in the presence of alkali, salicylaldehyde and allyl haloalkane are made to perform a nucleophilic substitution reaction, so that a nucleophilic substitution product is obtained; secondly, the product generated in the step (1) is heated to perform a Claisen rearrangement reaction; (3) the product obtained in the step (2) and ethylenediamine are condensed in an organic solvent, so that a Salen ligand is obtained; (4), in an ether solvent, the Salen ligand and divinyl benzene are copolymerized in the presence of a radical initiator and an auxiliary initiator, so that a Salen organic polymer of a mesoporous structure is obtained; and (5) in a mixed solvent of alcohol and water, the Salen organic polymer is used as a carrier, and mesoporous Salen organic polymer Co catalyst is obtained through preparation. The catalyst prepared through the preparation method is applied to catalytic oxidation of benzoin and has good catalytic activity, and meanwhile, even the catalyst is repeatedly used, the catalytic activity of the catalyst cannot be lowered.

Description

[0001] Technical field: [0002] The invention belongs to the field of organic material synthesis, and in particular relates to a preparation method of a Salen organic polymer with a mesoporous structure and a Co catalyst thereof, and applies the catalyst to the catalytic oxidation of benzoin to obtain benzil. [0003] Background technique: [0004] Metal Salen complexes are an important class of organic reaction catalysts, which can catalyze many important organic reactions with high yield and high selectivity under very mild conditions, such as: Diels-Alder reaction, olefin epoxidation, Strecker reaction, catalytic oxidation, etc. In addition, from the structural analysis, the Salen ligand has the advantages of simple synthesis, easy structure modification, and coordination with various metals (Cr, Al, Co, Cu, Zn, Ni, etc.), and has received extensive attention from chemists. . Classic metal-Salen catalyzed reactions are generally carried out in homogeneous systems. Althou...

Claims

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Application Information

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IPC IPC(8): B01J31/28B01J31/06B01J32/00B01J35/10C07C45/38C07C49/784
CPCC07C45/38B01J31/063B01J31/28B01J2231/70B01J35/612B01J35/615C07C49/784
Inventor 朱余玲
Owner SHAOXING UNIVERSITY
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