Application of chitosan/cellulose composite microsphere immobilized copper in preparation of diphenyl silane compound

A technology of diphenylsilane and composite microspheres, which is applied in the fields of compounds of group 4/14 elements of the periodic table, silicon organic compounds, metal/metal oxide/metal hydroxide catalysts, etc., which can solve the problem that catalysts cannot be recycled , high cost, incapable of industrialization and other problems, to achieve good biocompatibility, long service life and good effect

Pending Publication Date: 2021-09-24
HUBEI ENG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The invention provides a preparation method of chitosan/cellulose composite microsphere-immobilized copper metal catalytic material (CC@Cu) and its application to the method of converting p-benzoquinone methyl compound to prepare diphenylsilane compound. It aims to overcome the following deficiencies in

Method used

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  • Application of chitosan/cellulose composite microsphere immobilized copper in preparation of diphenyl silane compound
  • Application of chitosan/cellulose composite microsphere immobilized copper in preparation of diphenyl silane compound
  • Application of chitosan/cellulose composite microsphere immobilized copper in preparation of diphenyl silane compound

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Embodiment 1

[0041] The active component of the CC@Cu catalytic material provided by the embodiment of the present invention is copper, and the carrier is chitosan / cellulose composite microspheres; meanwhile, the relative content of the active component copper in the CC@Cu catalytic material is 1.75 mmol / g.

[0042] Among them, the carrier is chitosan / cellulose composite microspheres, and the chitosan / cellulose composite microspheres are cellulose mixed with chitosan in an acidic mixed solution, then added to an alkaline solution to suspend to form microspheres, and succinic dialdehyde is added to form microspheres. Combined composite microspheres. Subsequently, copper ions were adsorbed to form chitosan / cellulose composite microsphere-immobilized copper catalytic material (CC@Cu).

[0043] The embodiment of the present invention also provides a preparation method of CC@Cu catalytic material, which includes three major steps:

[0044] 1) Preparation of chitosan / cellulose microspheres: Add...

Embodiment 2～4

[0050] The CC@Cu catalytic material is prepared by the method of Example 1, the difference is that in the second) step of Example 2, the chitosan unit body: succinic dialdehyde=1mol:1mol, this time may be due to incomplete crosslinking, microspheres Be transparent, fragility and variability, promptly get rid of this ratio; In the 2nd) step of embodiment 3, chitosan unit body: succinic dialdehyde=1mol:2mol, possibly cross-linking is incomplete, and microsphere is transparent, easily Denaturation; in the 2nd) step of embodiment 4, chitosan unit body: succinic dialdehyde=1mol:6mol, microsphere is partial brown solid shape, stable form. combine figure 2 And embodiment 1 to the infrared spectroscopic analysis of catalytic material, when the-C=O of succinaldehyde and the-NH of chitosan unit body 2 When it is 2:1 or 4:1, the crosslinking is not complete, and all the ketone groups attributable to succinic dialdehyde participate in the Schiff base reaction and acetalization reaction,...

Embodiment 5

[0052] The embodiment of the present invention also provides a method of applying CC@Cu catalytic material to the silicon addition reaction between p-benzoquinone methyl compound I and diboronic acid pinacol dimethyl silicon reagent, the specific steps are as follows: p-benzoquinone Methyl compound, diboronic acid pinacol dimethyl silicon reagent and CC@Cu catalytic material (prepared in Example 1) were added to the mixed solvent of 5ml water according to the molar ratio of 1:1.2:0.01, and the CC@Cu catalytic material The ratio of the amount to water is 0.002mmol: 2ml, and stirred at room temperature for 12h; after filtering the CC@Cu catalytic material, extracting and spinning the solvent, and separating by thin layer chromatography, the p-benzoquinone methyl compound and bis-benzoquinone methyl compound are obtained. The product of the silicon addition reaction between boric acid pinacol dimethyl silicon reagents is diphenylsilane compound II. At the same time, the CC@Cu cat...

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Abstract

The invention relates to an application of chitosan/cellulose composite microsphere immobilized copper in preparation of the diphenyl silane compound, the catalytic material takes chitosan/cellulose composite microspheres as the carrier, and an active component is copper; the specific content is as follows: the chitosan/cellulose composite microsphere immobilized copper catalytic material (CC@Cu) is taken as the catalyst, the bis (pinacolato) diboron dimethyl silicon reagent is taken as the silicon reagent, pure water is taken as the solvent, and silicon addition reaction is respectively carried out on p-benzoquinone methyl compounds containing different substituent groups to obtain the diphenyl silane compound. The CC@Cu catalytic material disclosed by the invention is high in catalytic activity, can be applied to catalysis of silicon addition reaction of various different types of p-benzoquinone methyl compounds, and has the advantages of small catalyst dosage, mild reaction conditions and high product yield; in addition, the pure water is used as the solvent, operation is carried out at room temperature, and operation is simple and easy; the applicability is wide, and the characteristic of the one-pot method is achieved; besides, the catalytic material can be repeatedly used for multiple times, so that the cost is saved, and the catalyst is environment-friendly and suitable for industrial application.

Description

technical field [0001] The present invention relates to the preparation of a kind of catalytic material and its application in p-benzoquinone methyl compound, in particular to a chitosan / cellulose composite microsphere immobilized copper catalytic material (Chitosan / Cellulose-Cu 2+ =CC@Cu) and its application in the preparation of diphenylsilane compounds. Background technique [0002] In recent years, organosilicon compounds have attracted special attention due to their wide applications in materials science and medicinal chemistry. Organosilanes are versatile intermediates in organic synthesis because C-Si bonds are easily converted to C-O bonds and C-C bonds. p-Benzoquinone methides are reactive intermediates consisting of cyclohexadiene moieties with carbonyl and exomethylene groups that react rapidly with nucleophiles to form various diphenyl derivatives, but so far, The silicon addition to the exocyclic double bond of p-benzoquinone methyl compounds to form diphenyls...

Claims

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Application Information

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IPC IPC(8): C07F7/08B01J31/06B01J23/72B01J35/08
CPCC07F7/081C07F7/0829B01J31/06B01J23/72B01J35/08B01J2231/342
Inventor 朱磊韩彪张泽浪赵雪李铭超李博解张瑶瑶何边阳汪连生
Owner HUBEI ENG UNIV
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