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Bi(2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical) ether ester and method of preparing the same

A technology of tetramethylpiperidine nitroxide free radicals and ether ester compounds, which is applied in the field of diether esters and their preparation, hindered amine polymerization inhibitors, and can solve the problem of reducing the number of nitroxide free radicals and increasing the use of polymerization inhibitors Large and other problems, to achieve the effect of extensive sources, cheap prices, and easy industrial production

Inactive Publication Date: 2009-04-08
HUAIHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the number of nitroxide free radicals contained in the unit mass of the above-mentioned polymerization inhibitors is greatly reduced, which will inevitably lead to an increase in the use of such polymerization inhibitors in the production or refining process of high-boiling point olefin monomers.

Method used

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  • Bi(2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical) ether ester and method of preparing the same
  • Bi(2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical) ether ester and method of preparing the same
  • Bi(2,2,6,6-tetramethyl piperidine nitrogen oxygen free radical) ether ester and method of preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation of bis(2,2,6,6-tetramethylpiperidine nitroxyl radical) ether ester: Weigh commercially available 1-oxy-4-hydroxy-2,2,6,6-tetramethyl 17 grams of piperidine, dissolved in 60 grams of 1,4-dioxane solvent, temperature controlled at 40 to 45 °C, 13 grams of solid sodium tert-butoxide was added under stirring, and 8 grams of chlorine was added dropwise after nitrogen was introduced for 2 hours. Acetyl chloride, after the dripping is completed, 0.5 g of tetrabutylammonium iodide is added, and after the reaction is incubated for 1 hour, the temperature is raised and refluxed for 8 hours. After the reaction was cooled, the reaction product was poured into 100 grams of water, the dark red solid was filtered out, and recrystallized with 200 grams of isobutanol to obtain red crystalline bis(2,2,6,6-tetramethylpiperidine) nitroxyl radical) ether ester 17.3 g, yield 90%. Melting point 157.2~158.1 ℃.

[0015] IR (KBr tablet, cm -1 ): 2948, 2837, 1735, 1324, 1183.

[0...

Embodiment 2

[0018] According to the preparation method and steps of Example 1, the solid sodium tert-butoxide in Example 1 was replaced with a 28% sodium ethoxide ethanol solution to obtain bis(2,2,6,6-tetramethylpiperidine nitrogen) Oxygen radical) ether ester 15.2 g, yield 78%.

Embodiment 3

[0020] According to the preparation method and steps of Example 1, the solvent of Example 11, 4-dioxane was changed to dimethyl sulfoxide to obtain bis(2,2,6,6-tetramethylpiperidine in red crystals) nitroxyl radical) ether ester 13.9 g, yield 72%.

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PUM

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Abstract

The invention relates to bis (2, 2, 6, 6-tetramethyl-1-piperidine-N-oxyl free radical) ether ester, which has a chemical structure shown in a general formula (I). The bis (2, 2, 6, 6-tetramethyl-1-piperidine-N-oxyl free radical) ether ester has the advantages of simple and convenient preparation method, easy industrialization and high product yield, and can be used as an inhibitive substance to be applied to producing and refining processes of an alkene monomer or an alkene cross-linking agent.

Description

technical field [0001] The invention relates to a hindered amine polymerization inhibitor, in particular to bis(2,2,6,6-tetramethylpiperidine nitroxide radical) ether ester and a preparation method thereof, belonging to the field of fine chemicals. technical background [0002] In the production or purification process of various olefin monomers such as styrene, acrylates, butadiene, etc., 2,2,6,6-tetramethylpiperidinol nitroxide radicals or other polymerization inhibitors are widely used Dosage compound. Since the molecular weight of 2,2,6,6-tetramethylpiperidinol nitroxide radical is relatively small, it is more suitable for the production or purification process of low-boiling olefin monomers. However, in the production or refining process of high-boiling olefin monomers, 2,2,6,6-tetramethylpiperidinol nitroxyl radicals with high volatility or dispersibility will be entrained in high-boiling olefin monomers. This results in a decrease in the purity of olefin monomers. ...

Claims

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Application Information

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IPC IPC(8): C07D211/94C07C7/20C09K15/30
Inventor 张田林刘霖周杰兴
Owner HUAIHAI INST OF TECH
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