Process for preparing N-hydroxyalkyl compound and isocynauric acid tri (2-ethoyl) ester composition

A compound and hydroxyalkyl technology, applied in the field of preparing N-hydroxyalkyl compounds and isocyanurate triester compositions, can solve the problems of polluting products, reducing product quality, hindering product use, etc.

Inactive Publication Date: 2003-07-09
NIPPON SHOKUBAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this synthetic method, impurities from the catalyst can also contaminate the product, hinder its use in different applications, or reduce the quality of the product, so further improved inventions are needed in this regard

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Addition reaction of ethylene oxide and isocyanuric acid was carried out using the ion exchanger obtained in catalyst preparation method 1.

[0073] Specifically, 20 ml of water-swellable ion exchanger, 9.7 g of isocyanuric acid, 37.5 g of methyl-cellosolve, and 9.9 g of ethylene oxide were continuously added at 90° C. under a nitrogen atmosphere within 1 hour. Thermometer, pressure gauge, stirrer, etc. in the autoclave. As the water-swellable ion exchanger, a wet product prepared by metering with a graduated cylinder, and performing solvent replacement of methyl-cellosolve and suction-filtration was used. Then, the reaction mixture was incubated at 90°C for 6 hours to synthesize tris(2-hydroxyethyl)isocyanurate. The above methyl cellosolve was added such that the total amount of methyl cellosolve including the content in the ion exchanger was 37.5 g. From the colorless transparent solution obtained after completion of the reaction, the ion exchanger can be recovered ...

Embodiment 2

[0075] Using the ion exchanger recovered by filtration in Example 1, the experiment was repeated in the same manner as in Example 1. From the colorless transparent solution obtained after the completion of the reaction, the ion exchanger can be recovered by filtration, and the obtained filtrate can be analyzed by high performance liquid chromatography. It can be seen from the analysis that the conversion rate of isocyanuric acid is 99.0 mol%, and the yield of tris(2-hydroxyethyl) isocyanurate is 84.7 mol%. Catalyst activity does not decrease due to repeated catalytic reactions. From this solution, methyl-cellosolve can be recovered, and after cooling the solution, white solid crystals can be isolated. The crystals can be recovered by filtration and drying. The resulting white solid crystals were found to contain tris(2-hydroxyethyl)isocyanurate with a purity of 99.0%.

[0076] The crystals thus obtained can be analyzed with a thermal analyzer (product of Shimadzu Corporatio...

Embodiment 3

[0078] Using the cross-linked polymer recovered by filtration in Example 2, 5 additional repeated experiments were performed in the same manner as in Example 2. From the colorless transparent solution obtained after completion of the fifth reaction, the cross-linked polymer was recovered by filtration, and the resulting filtrate was analyzed by high performance liquid chromatography. It can be seen from the analysis that the conversion rate of isocyanuric acid is 99.0 mol%, and the yield of tris(2-hydroxyethyl) isocyanurate is 82.5 mol%. From this solution, the methyl-cellosolve can be removed and 26.0 g of the crude product obtained are recrystallized by adding 24.0 g of ethanol. After cooling the solution, a crystalline white solid can be isolated. The precipitate was recovered by filtration and dried. The resulting white solid crystals were found to contain tris(2-hydroxyethyl)isocyanurate with a purity of 99.8%.

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Abstract

The object of the present invention is to provide a process for producing an N-hydroxyalkyl compound which is not only conducive to suppression of the discoloration due to decomposition of the solvent and suppression of formation of impurities originating from the catalyst but also insures a high selectivity of reaction and a tris(2-hydroxyethyl) isocyanurate composition suppressed in discoloration, lean in impurity, with high resistance to heat and, hence, of good quality. The present invention is directed to a process for producing an N-hydroxyalkyl compound comprising the reaction of an amido or imido group-containing compound and an epoxy compound in the presence of a catalyst, wherein the catalyst is a solid ion exchanger.

Description

technical field [0001] The present invention relates to a process for the preparation of N-hydroxyalkyl compounds and tris(2-hydroxyethyl)isocyanurate compositions. Background technique [0002] N-hydroxyalkyl compounds are industrially important compounds, which can be used as raw materials or solvents for polyester resins, polyurethane resins, oxazolidinones, fabric treating agents, plasticizers, and the like. Among N-hydroxyalkyl compounds, tris(2-hydroxyethyl) isocyanurate [abbreviation: THEIC] having hydroxyethyl groups on all nitrogen atoms of the triazine ring is not only due to the presence of the triazine ring, It has excellent performance in heat resistance and flame retardancy, and has good compatibility, making it very suitable as a raw material for insulating varnishes, various coating resins, stabilizers for vinyl chloride resins, or flame retardants for various plastics. it works. [0003] Japanese Examined Publication Show-43-26862 discloses a method includ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/34
CPCC07D251/34
Inventor 森田武彦森口敏光
Owner NIPPON SHOKUBAI CO LTD
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