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A kind of preparation method and application of chiral zr-mof catalyst

A catalyst and chirality technology, applied in the field of chiral catalyst preparation, can solve the problems of poor chiral selectivity and cannot be reused, and achieve the effects of short reaction time, easy recovery and cost reduction

Inactive Publication Date: 2021-08-27
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the preparation is mainly by the reaction of aldehyde and cyanosilane, but the chiral selectivity is relatively poor. In addition, the catalyst is generally a homogeneous catalyst and cannot be reused.

Method used

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  • A kind of preparation method and application of chiral zr-mof catalyst
  • A kind of preparation method and application of chiral zr-mof catalyst
  • A kind of preparation method and application of chiral zr-mof catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Embodiment 1 (R)-6, the synthesis of 6'-dibromo-1,1'-bi-2-naphthol

[0058] Weigh the raw material R-1,1'-bi-2-naphthol (10.0mmol, 2.86g) into a 100ml three-necked flask, add 20.0g of dichloromethane, cool to 0°C, and slowly add liquid bromine ( 25.2mmol, 4.0g), after the dropwise addition was completed, the reaction solution was light orange. Maintain the temperature and continue the reaction for 24h, then add Na 2 S 2 o 3 (7.4mmol, 1.20g) in aqueous solution, continue to stir for 2h. After the reaction was completed, the color of the reaction solution changed from orange to light yellow. Filter the reaction solution, transfer the filtrate to a separatory funnel, wash the organic phase three times with a saturated NaCl solution, combine the organic phases, and add an appropriate amount of NaCl 2 SO 4 After drying, the solvent was removed by rotary evaporation to obtain (R)-6,6'-dibromo-1,1'-bi-2-naphthol as a light yellow solid product.

Embodiment 2

[0059] Example 2 (R)-6,6'-dibromo-2,2'-diethoxy-1,1'-binaphthyl synthesis

[0060] Weigh the raw material (R)-6,6'-dibromo-1,1'-bi-2-naphthol (10.0mmol, 4.44g) into a 100ml flask, add 40.0ml of acetone, stir until the solids are completely dissolved, Then add anhydrous K 2 CO 3 (40.0mmol, 5.50g), bromoethane (60.0mmol, 7.00g), the reaction system was heated to reflux, and the temperature was maintained for 48h. After the reaction was completed and dropped to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure to obtain the yellow solid product (R)-6,6'-dibromo-2,2'-diethoxy-1,1'-binaphthyl .

Embodiment 3

[0061] Embodiment 3 (R)-6, the synthesis of 6'-dichloro-2,2'-diethoxy-1,1'-binaphthalene

[0062] N 2 Under protection, the raw material (R)-6,6'-dibromo-2,2'-diethoxy-1,1'-binaphthalene (10.0mmol, 4.97g), cuprous chloride (22.0mmol, 2.20g), DMF 15.0ml was placed in a 100ml three-neck flask, and stirred at a constant temperature of 110°C for 48h. After the reaction was completed, it was filtered while it was hot, and the filtrate was poured into 300ml of secondary water while stirring, and a pale yellow solid was precipitated. After filtration, the solid was dried and dissolved in dichloromethane. After column chromatography (eluent: dichloromethane), the product 6,6'-dichloro-2,2'-diethoxy-1,1 was obtained as a yellow solid '-binaphthyl.

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Abstract

The invention relates to a preparation method and application of a chiral Zr-MOF catalyst, which belongs to the technical field of preparation of chiral catalysts. The structural formula of an organic ligand L of a chiral Zr-MOF catalyst is: (R)-4,4' ‑Dimethoxycarbonyl‑6,6'‑dichloro‑2,2'‑diethoxy‑1,1'‑binaphthyl reacted with sodium hydroxide to obtain organic ligand L. Organic Ligand L and ZrCl 4 Chiral Zr-MOF catalysts were prepared by solvothermal reaction. The step of the method for preparing α-nitrile alcohol by chiral Zr-MOF catalyst is to put benzaldehyde, TMSCN, Zr-MOF into the container, add solvent acetonitrile and stir, through centrifugation, decompression rotary evaporation concentration, column chromatography, acidification treatment , separation and drying to obtain α-nitrile alcohol. The chiral selectivity of the chiral α-nitrile alcohol obtained by catalyzing the reaction of benzaldehyde and cyanosilane with the chiral catalyst of the present invention is 97-99%.

Description

technical field [0001] The invention belongs to the technical field of chiral catalyst preparation, and in particular relates to a preparation method and application of a chiral metal-organic framework. Background technique [0002] Metal-organic frameworks (MOFs) have become a research hotspot in the field of materials chemistry due to their exceptionally high specific surface area and tunable pores. One of the main features of Zr-MOF is that the metal has a high oxidation state. Due to the high charge density and relatively large bond polarity, there is a strong interaction between the metal Zr and the O atom in the carboxylic acid ligand. On the other hand, Zr ions and carboxylic acid ligands can be regarded as hard acid and hard base, respectively, so there is a strong coordination bond between them. Therefore, this determines that Zr-MOF has good stability in organic solvents and aqueous solutions, which also lays the foundation for the wide application of Zr-based MOF...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C65/24B01J31/16B01J31/22C08G83/00C07F7/18C07C253/30C07C51/09
CPCB01J31/1691B01J31/2239B01J2231/343B01J2531/48C07B2200/07C07C65/24C07C253/30C08G83/008C07C255/36
Inventor 陈功军赵晨晨靳法征董育斌
Owner SHANDONG NORMAL UNIV
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