Synthesis method and application of trialkynyl monomer 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-triketone

A technology for the synthesis of propargyl triargyl, which is applied in the field of synthesis of alkyne-based organic monomers, can solve the problems of difficult recovery of organic solvents, complex post-treatment processes, and large environmental impact, and achieves low cost, low production cost, and economical production. resource effect

Inactive Publication Date: 2011-04-27
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Regarding the preparation of 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione, it has been documented that potassium cyanate, propyne bromide can be prepared in dimethylformamide or the alkaline salt solution of dimethyl sulfoxide, but this method has a low yield in the solvent dimethyl sulfoxide, and the organic solvent used in the reaction is difficult to recycle, has a large impact on the environment, and relatively high cost, The post-processing process of the product is complicated, and the introduction of highly toxic solvents such as benzene

Method used

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  • Synthesis method and application of trialkynyl monomer 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-triketone
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  • Synthesis method and application of trialkynyl monomer 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-triketone

Examples

Experimental program
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Effect test

Embodiment 1

[0026] In the present embodiment, the synthetic method of 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione is carried out according to the following process:

[0027] Add 6.45g (0.05mol) of isocyanuric acid, 8g (0.2mol) of sodium hydroxide, 2.78g (0.01mol) of tetrabutylammonium chloride and 100mL of water into a 250mL round-bottomed three-neck flask, heat up and stir until the isocyanuric acid Dissolve, then add 47.6g (0.4mol) propyne bromide dropwise with a constant pressure dropping funnel, react at 75°C for 20 hours, cool to room temperature after the reaction is complete, separate the product and the water phase, wash the product with distilled water, and wash away NaBr, NaOH, etc., and then washed with absolute ethanol, and dried under vacuum at 55° C. for 6 hours to obtain 7.2 g of a white solid product with a yield of 59.26%.

[0028] In this embodiment, the preparation method of poly 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione is to take 1,3,5-tripropargyl-1 , 3,5-tr...

Embodiment 2

[0031] In this example, the preparation process of 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione is the same as Example 1, except that the reaction temperature is 80°C , the reaction time was 15 hours, and 7.6 g of 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione was prepared with a yield of 62.55%.

[0032] The preparation method of poly-1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione in this example is the same as that in Example 1.

Embodiment 3

[0034] In this embodiment, the preparation process of 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione is the same as in Example 1, except that the amount of propyne bromide is added It was 35.67g (0.3mol), and 5.8g of 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione was prepared with a yield of 47.74%.

[0035] The preparation method of poly-1,3,5-tripropargyl-1,3,5-triazine-2,4,6-trione in this example is the same as that in Example 1.

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Abstract

The invention discloses a synthesis method and application of a trialkynyl monomer 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-triketone. The synthesis method comprises: isocyanuric acid and propargyl bromide as raw materials are utilized to synthesize the trialkynyl monomer in the presence of a phase transfer catalyst; and poly 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-triketone is obtained after 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-triketone is cured at high temperature. The synthesis method has the beneficial effects of high safety, low raw material cost and mild reaction conditions, is simple in operation and easy for scale production.

Description

1. Technical field [0001] The invention relates to a method for synthesizing an alkynyl organic monomer, in particular a trialkynyl monomer 1,3,5-tripropargyl-1,3,5-triazine-2,4,6-tri Synthesis methods and applications of ketones. 2. Background technology [0002] Alkyne-based resins are a new type of thermosetting resins. This type of resin has high reactivity. Under the conditions of heat, radiation or catalysts, alkyne groups can react to form aromatic rings or conjugated polyene structures. This type of resin has different advantages from other resins, such as: no volatile by-products are produced during the curing process, and a dense cured product is obtained; the cured product has good heat resistance and mechanical properties, and can be used in harsh conditions. The basic performance of the material can be maintained under the condition of the alkyne-based resin has been a hot research topic. In recent years, the focus of research is to introduce polycyclic struct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/30C08G61/12
Inventor 史铁钧杨兆攀
Owner HEFEI UNIV OF TECH
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