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A kind of sba-15 immobilized 2-azaadamantane nitroxide radical catalyst and its preparation and application

A nitroxide radical and azaadamantane technology is applied in the field of mesoporous molecular sieve SBA-15 immobilized 2-azaadamantane nitroxide radical catalyst, which can solve the complex synthesis process, practical application restriction and high synthesis cost. question

Active Publication Date: 2021-06-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-Azaadamantane-nitroxyl radicals and their derivatives are relatively complex and costly compared to TEMPO and their derivatives that have been industrially produced. Therefore, if the catalyst cannot be reused well, 2- The practical application of azaadamantane-nitroxyl radicals and their derivatives will be greatly restricted

Method used

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  • A kind of sba-15 immobilized 2-azaadamantane nitroxide radical catalyst and its preparation and application
  • A kind of sba-15 immobilized 2-azaadamantane nitroxide radical catalyst and its preparation and application
  • A kind of sba-15 immobilized 2-azaadamantane nitroxide radical catalyst and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of SBA-15 Immobilized 2-Azaadamantane-Nitroxy Free Radical Catalyst

[0022] Add 1.0 g of surface carboxylated SBA-15, 84 mg of 1-methyl-2-azaadamantyl-4-(phenyl)methanol (0.33 mmol) to a 100 mL one-necked bottle equipped with a magnetic stirrer, EDCI (0.66mmol), DMAP (0.36mmol), replace the air in the reaction flask with nitrogen, and inject triethylamine (0.66mmol) and 15mL of dichloromethane. Stir the reaction at room temperature for 24 hours, filter, wash with dichloromethane, and vacuum-dry to constant weight to obtain grafted SBA-15.

[0023] Add the grafted SBA-15 obtained above and 15 mL of tetrahydrofuran into a 50 mL single-necked bottle equipped with a magnetic stirrer, slowly add m-CPBA (0.66 mmol), react at room temperature for 4.5 h, filter, wash with dichloromethane, Vacuum dried to constant weight to obtain SBA-15 immobilized 2-azaadamantane-nitroxyl radical catalyst.

Embodiment 2

[0024] Example 2: Preparation of SBA-15 Immobilized 2-Azaadamantane-Nitroxy Free Radical Catalyst

[0025] The preparation process is the same as in Example 1, except that the amount of 1-methyl-2-azadamantyl-4-(phenyl)methanol is changed to 64mg (0.25mmol), the amount of EDCI is changed to (0.6mmol), and the amount of DMAP is changed to (0.23mmol), the organic base was changed to diisopropylethylamine (0.5mmol), and the amount of m-CPBA was changed to 0.6mmol. Finally, the SBA-15 immobilized 2-azaadamantane-nitrogen radical catalyst was prepared.

Embodiment 3

[0026] Example 3: Application of SBA-15 Immobilized 2-Azaadamantane-Nitroxy Free Radical Catalyst in Alcohol Oxidation

[0027] Add benzyl alcohol (1mmol), KBr (0.1mmol), SBA-15 immobilized 2-azadamantane-nitroxyl radical catalyst 0.1g (prepared in Example 1) to the 15mL sealed tube equipped with a magnetic stirrer , acetonitrile 1 mL, saturated NaHCO 3 Solution 0.7mL. Place the sealed tube in a 5°C ice-water bath, and slowly add NaClO and NaHCO dropwise 3 Add NaHCO in the mixed solution (concentration is 7.5% NaClO solution 1.67g (1.7mmol) 3 Saturated solution 1.2mL). After the dropwise reaction was completed, the reaction was carried out for 10 minutes. Samples were taken and monitored by GC. The conversion rate of benzyl alcohol was 99.7%, and the selectivity of the product benzaldehyde was 100%.

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Abstract

The invention discloses a SBA-15 immobilized 2-azaadamantane nitrogen oxide free radical catalyst and its preparation and application. The surface carboxylated SBA-15 and 1-methyl-2-azaadamantyl- 4-(phenyl)methanol is a raw material, with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide as a condensation agent, with 4-dimethylaminopyridine as a catalyst, in dichloromethane Perform condensation reaction in a solvent, filter, wash, and vacuum dry to obtain grafted SBA-15; in tetrahydrofuran solvent, oxidize the grafted SBA-15 with m-chloroperoxybenzoic acid under nitrogen protection at room temperature, filter, After washing and drying, the SBA-15 immobilized 2-azaadamantane-nitrogen radical catalyst is obtained. SBA‑15 supported 2‑Azaadamantane‑Nitroxy free radical catalyst can be used for the oxidation reaction of alcohols.

Description

technical field [0001] The invention belongs to the technical field of heterogeneous nitrogen-oxygen free radical catalysis, and in particular relates to a mesoporous molecular sieve SBA-15 immobilized 2-azaadamantane nitrogen-oxygen free radical catalyst and its preparation and application method. The catalyst is heterogeneous Catalyst, which can be used to catalyze the oxidation reaction of alcohol. Background technique [0002] The selective oxidation of alcohols to aldehydes and ketones is a very extensive and important unit reaction in organic synthesis, and has been widely used in both industrial production and laboratory research. Therefore, various oxidation systems have been developed for the oxidation of alcohols. 2,2,6,6-Tetramethylpiperidine-1-oxide (TEMPO) is a stable nitroxide free radical, which is easy to prepare and cheap. Stable nitroxide radicals represented by TEMPO have been widely used to catalyze the oxidation of alcohols. Although TEMPO can efficie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/02C07F7/08C07C47/54C07C49/407C07C45/30
CPCB01J31/0275B01J2231/763C07B2200/03C07B2200/11C07C45/30C07F7/0834C07C2601/14C07C47/54C07C49/407
Inventor 沈振陆田阳武马佳颀李美超
Owner ZHEJIANG UNIV OF TECH
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