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Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system

A hindered amine compound, heterogeneous catalysis technology, applied in the direction of organic chemistry and the like, can solve the problems that the preparation method cannot be simple, the purity requirement is high, and the catalyst cost is high, and achieves easy post-processing, high yield, and simple preparation process. Effect

Active Publication Date: 2021-09-24
TIANJIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The high-efficiency catalysis of bicarbonate alleviates the problems of high catalyst cost, high environmental pressure and low catalytic efficiency in the above-mentioned catalytic system to a certain extent. The purity requirement of the product is relatively high, and this preparation method cannot meet the demand of the market simply and efficiently, and further improvement is still needed
At the same time, the combination of bicarbonate and Bronsted acid catalysis can easily produce salt in the catalytic system and produce a certain amount of solid waste

Method used

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  • Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system
  • Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system
  • Method for preparing hindered amine nitroxide free radical compound by alkaline heterogeneous catalysis system

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Alkaline non-uniform catalytic system preparation preparation of gamlamine nitrogen oxygen free radical compound (2-chloro-4,6-double (2,2,6,6-tetramethylpioadhoxy radical-4-butyl) Method of triazine)

[0040] Take 2 g (4 mmol) 2-chloro-4,6-bis (2,2,6,6-tetramethylpiperidine-4-butyl amino) triazine I added to 50 ml of two round bottom flasks, assembly thermometer The sleeve is added 10 ml of toluene to the reaction container to dissolve the compound of formula I, and maintain the reaction system at 30 ° C, while continuously stirring, the reaction system is adjusted by 0.2 g / mL of sodium carbonate solution to 10.3, slow drop 0.8 mL 50% (mass concentration) hydrogen peroxide (20 mmol), reaction, TLC indicates the end point (about 20h), stopped the reaction, phase phase, and dry the organic phase after drying with anhydrous sodium sulfate, concentrated organic phase to obtain a goal The compound of the product formula IV 2.24 g red solid, yield is 99%, purity 99%.

[0041] ...

Embodiment 2

[0043] Method for preparing an alkaline non-uniform catalytic system (2,2,6,6-tetramethylpiperidine-4-alcohol nitrogen oxyfitride)

[0044] 2 g (12 mmol) 2,2,6,6-tetramethylpiperidine-4-alcohol II-1 was added to 50 ml of two round bottom flasks, assembled the thermometer sleeve, and 10 ml of ethyl acetate was added to the reaction vessel. The reaction solvent dissolves the compound of the II-1, and the reaction system is maintained at 30 ° C, and the reaction system is continuously stirred, and the reaction system pH is 9.0, and 2.4 ml of 30% (mass concentration) is adjusted slowly. The hydrogen peroxide (24 mmol) was carried out, the TLC indicates the end point (about 6 h), stopped the reaction, phase-phase, after collecting the organic phase, dried over anhydrous sodium sulfate, concentrated organic phase to obtain a target product V-1 2.04 g of red solid, yield is 99%, purity 98%.

[0045]

Embodiment 3

[0047] Method for preparing an alkaline non-apex catalytic system (2,2,6,6-tetramethylpiperidine-4-ketozo-free radical)

[0048] 2 g (12 mmol) 2,2,6,6-tetramethylpiperidine-4-ketone (II-2) was added to 50 ml of two round bottom flasks, fitting a thermometer sleeve, and 10 ml of reaction solvent was added to the reaction vessel. (5 ml of xylene, 5 ml of ethyl acetate) dissolves the compound of formula II-2, and maintains the reaction system at 40 ° C, while continuously stirring, using 0.01 g / ml of potassium hydrogencarbonate aqueous solution, regulating the reaction system pH 7.5, The reaction was slowly added dropwise to the hydrogen peroxide (36 mmol) of hydrogen peroxide (36 mmol), TLC indicates the end point (about 6h), stopped the reaction, phase-phase, and dry the organic phase after drying, concentrated organic phase The compound 1.99 g of the compound of the Target product V-2 was obtained, and the yield was 97%, purity 99%.

[0049]

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Abstract

The invention discloses a method for preparing a hindered amine nitroxide free radical compound by using an alkaline heterogeneous catalysis system, which comprises the steps of dissolving a hindered amine compound in an organic solvent, adjusting the pH value by using a carbonate aqueous solution, and adding a hydrogen peroxide aqueous solution for reaction to generate the hindered amine nitroxide free radical compound shown as a formula (IV), (V) or (VI) defined in the description. The method is high in universality, and hindered amine nitroxide free radical compounds of various structures are prepared; the method is high in catalytic activity, short in reaction time, high in yield, simple in preparation process and convenient to operate, a high-purity target product can be obtained through simple phase splitting, drying and concentration in the post-treatment process, and meanwhile, an aqueous solution system and ethyl acetate can be repeatedly recycled; and byproducts are few.

Description

Technical field [0001] The present invention relates to the field of chemical synthesis, and more particularly to a method of preparing a preparation of a resistant amine nitrogen oxygen radical compound. Background technique [0002] The hindered amine nitrogen-free radical compound is an important fine chemical, which can be used directly as a capture agent, a probe or a polymerization agent, or further prepared such a low alkaline alkoxy-resistant amine light stabilizer. Therefore, in human production, there is a large market demand for hindered amine nitrogen oxygen free radicals. [0003] In the current report, the preparation of the hindered amine nitrogen-free radical compound mainly uses the active metal to catalyzes, the most classic method is to prepare the preparation of the preparation ammine nitrogen oxygen free compound using a sodium hydrogen peroxide catalytic system. The reaction is: [0004] [0005] However, the homogeneous catalyst is difficult to recover an...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D211/94
CPCC07D401/14C07D211/94
Inventor 李阳许文胜陈立功闫喜龙王博威
Owner TIANJIN UNIV
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