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Diester sebacate (2,2,6,6-tetramethyl-4-hydroxypiperidine) nitroxide radical of high-efficiency polymerization inhibitor and production method thereof

A high-efficiency polymerization inhibitor, nitroxide free radical technology, applied in the direction of organic chemical methods, chemical instruments and methods, physical/chemical process catalysts, etc., can solve the problems of low product yield, adverse effects of transesterification, etc. High yield, low cost and little environmental pollution

Inactive Publication Date: 2011-05-04
NANTONG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the magnesium methoxide catalyst has the disadvantages of being easily hydrolyzed when it encounters water, the Ph value of the system is increased, which has an adverse effect on the transesterification reaction, and the product yield is low.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] In a four-necked flask equipped with a thermometer and a reflux condenser, add 24g (0.05mol) bis(2,2,6,6-tetramethyl-4-hydroxypiperidine) sebacate, a certain amount of 95% Ethanol solvent and 0.24g catalyzer, and catalyzer is respectively by (0.216g, 0.209g, 0.2g, 0.222g, 0.214g, 0.205g, 0.109g, 0.107g, 0.104g) sodium tungstate, (0.022g, 0.021g , 0.02g, 0.016g, 0.015g, 0.014g, 0.13g, 0.128g, 0.125g) tetrabutylammonium bromide, (0.002g, 0.01g, 0.02g, 0.002g, 0.011g, 0.021g, 0.001 g, 0.005g, 0.001g) of the catalytic system formed by the mixture of disodium ethylenediaminetetraacetate, then add 28.3g (0.25mol) of 30% hydrogen peroxide, start heating in the electric heating mantle and start electromagnetic stirring, and the electric heating mantle Adjust to the specified heating temperature of 65°C and start timing. The reaction time is 12 hours. After the reaction is over, cool to 50°C, add 25g of petroleum ether with a boiling range of 90-120°C, stir for 20 minutes, and s...

Embodiment 2

[0013] In a four-necked flask equipped with a thermometer and a reflux condenser, add 24g (0.05mol) bis(2,2,6,6-tetramethyl-4-hydroxypiperidine) sebacate, a certain amount of 95% Ethanol solvent and 0.24g catalyzer, and catalyzer is respectively by (0.216g, 0.209g, 0.2g, 0.222g, 0.214g, 0.205g, 0.109g, 0.107g, 0.104g) sodium tungstate, (0.022g, 0.021g , 0.02g, 0.016g, 0.015g, 0.014g, 0.13g, 0.128g, 0.125g) tetrabutylammonium bromide, (0.002g, 0.01g, 0.02g, 0.002g, 0.011g, 0.021g, 0.001 g, 0.005g, 0.001g) of the catalytic system composed of disodium ethylenediamine tetraacetate mixture, then add 19.2g (0.17mol) of 30% hydrogen peroxide, start heating in the electric heating mantle and start electromagnetic stirring, and the electric heating mantle Adjust to the specified heating temperature of 65°C and start timing. The reaction time is 12 hours. After the reaction is over, cool to 50°C, add 25g of petroleum ether with a boiling range of 90-120°C, stir for 20 minutes, and stand...

Embodiment 3

[0015] In a four-necked flask equipped with a thermometer and a reflux condenser, add 24g (0.05mol) bis(2,2,6,6-tetramethyl-4-hydroxypiperidine) sebacate, a certain amount of 95% Ethanol solvent and 0.24g catalyzer, and catalyzer is respectively by (0.216g, 0.209g, 0.2g, 0.222g, 0.214g, 0.205g, 0.109g, 0.107g, 0.104g) sodium tungstate, (0.022g, 0.021g , 0.02g, 0.016g, 0.015g, 0.014g, 0.13g, 0.128g, 0.125g) tetrabutylammonium bromide, (0.002g, 0.01g, 0.02g, 0.002g, 0.011g, 0.021g, 0.001 g, 0.005g, 0.001g) of the catalytic system composed of disodium edetate, then add 36g (0.32mol) of 30% hydrogen peroxide, start heating in the electric heating mantle and start electromagnetic stirring, adjust the electric heating mantle Start timing when the specified heating temperature is 65°C, and the reaction time is 12 hours. After the reaction is completed, cool to 50°C, add 25g of petroleum ether with a boiling range of 90-120°C, stir for 20 minutes, and stand still for 20 minutes. Then...

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PUM

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Abstract

The invention discloses a diester sebacate (2,2,6,6-tetramethyl-4-hydroxypiperidine) nitroxide radical of a high-efficiency polymerization inhibitor and a production method thereof. Diester sebacate (2,2,6,6-tetramethyl-4-hydroxypiperidine) and 30 percent of hydrogen peroxide are used as raw materials and react under the condition that a catalyst exists with the ratio of sodium tungstate, tetrabutylammonium bromide and disodium ethylene diamine tetraacetate to be 1:0.1-1.2:0.01-0.1 to obtain the diester sebacate (2,2,6,6-tetramethyl-4-hydroxypiperidine) nitroxide radical. By utilizing 30 percent of hydrogen peroxide as an oxidizer to synthesize the diester sebacate (2,2,6,6-tetramethyl-4-hydroxypiperidine) nitroxide radical and adopting a novel composite catalyst, the invention simplifiesthe separation and purification processes and has short reaction time, high product yield which reaches over 95 percent, higher product purity, great reduction of energy consumption, little environment pollution and low cost, thereby being a relatively ideal process for realizing industrial production.

Description

Technical field: [0001] The invention relates to a high-efficiency polymerization inhibitor sebacic acid bis(2,2,6,6-tetramethyl-4-hydroxypiperidine) ester nitroxide free radical and a production method thereof. Background technique: [0002] Bis(2,2,6,6-tetramethyl-4-hydroxypiperidine) sebacic acid nitroxide free radical is a new type of stable free radical discovered recently. Wide application is eye-catching. Because sebacic acid bis(2,2,6,6-tetramethyl-4-hydroxypiperidinyl) ester nitroxide free radical has excellent polymerization inhibition performance on unsaturated compounds, it has been used in the production of unsaturated monomer compounds in recent years. The application in the process is developing rapidly, so it is of great practical significance to replace the traditional phenolic polymerization inhibitors with hindered amine nitroxide free radical compounds. Sebacic acid di(2,2,6,6-tetramethyl-4-hydroxypiperidine) ester nitroxide free radical can be applied ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D211/94B01J31/02B01J31/04C07B63/04
Inventor 王树清高崇孙冬兵王歆然施振佺
Owner NANTONG UNIVERSITY