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Synthesis method of 1,3,5-tri-substituted perhydro-s-triazine

A synthesis method and technology of s-triazine, applied in 1 field, can solve problems such as low yield of hexahydro-s-triazine

Active Publication Date: 2010-06-09
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the 1,3,5-triacryloyl hexahydro-s-triazine yield of this method is relatively low

Method used

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  • Synthesis method of 1,3,5-tri-substituted perhydro-s-triazine
  • Synthesis method of 1,3,5-tri-substituted perhydro-s-triazine
  • Synthesis method of 1,3,5-tri-substituted perhydro-s-triazine

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Experimental program
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Effect test

preparation example Construction

[0019] a. Preparation of carrier

[0020] After mixing 0.20 mol of phenyltrimethoxysilane and 0.80 mol of tetraethoxysilane, 280 mL of ethanol was added, and vigorously stirred at 60° C. for 4 h. Then add 135mL cyclohexane, 280mL water and 0.01mol dodecylamine to the above mixed solution, mix well, place it at 80°C to age for 3 days, the reaction solution appears white precipitate, filter, filter out the solid, in vacuum Dry at 80°C for 10 hours under the same conditions, and bake at 350°C for 4 hours to obtain a phenyl-bonded polysiloxane material.

[0021] Introduction of b sulfonic acid group

[0022] After soaking the phenyl-bonded polysiloxane material in tetrachloroethane solution overnight, add 15% sulfur trioxide solution in tetrachloroethane, stir at 120° C. for 5 h, and then cool naturally to room temperature. Filter, wash until the pH is 6-7, and dry at 120° C. for 8 hours to obtain a catalyst phenylsulfonic acid functionalized silicon-based material.

Embodiment 1

[0024] Synthesis of 1,3,5-triphenylacetylhexahydro-s-triazine

[0025] In a three-neck flask equipped with mechanical stirring, a thermometer and a reflux condenser, add 0.3 mol of phenylacetonitrile, 0.075 mol of methanol formal, 70 mL of organic solvent 1,2-dichloroethane, and 0.9 g of catalyst, and heat to reflux under stirring. Continue to stir the reaction for 6h, stop heating, and the reaction ends. The reaction solution was filtered while it was hot, and after the solid catalyst was separated, the filtrate was distilled off under reduced pressure to remove the organic solvent 1,2-dichloroethane, cooled to room temperature, allowed to stand for 11 hours, and filtered to obtain 1,3,5-triphenylacetylhexa Hydrogen-s-triazine, the yield is 98.4%.

[0026] Structure Identification

[0027] Molecular formula: C 27 h 27 N 3 o 3

[0028] Elemental analysis: theoretical value: C 73.45 H 6.160 N 9.52;

[0029] Found: C 73.49 H 6.153 N 9.48.

[0030] Proton NMR spectrum: δ...

Embodiment 2

[0035] Synthesis of 1,3,5-triacetylhexahydro-s-triazine

[0036] In a three-neck flask equipped with a mechanical stirrer, a thermometer and a reflux condenser, add 0.5 mol of acetonitrile, 0.1 mol of ethanol formal, 80 mL of organic solvent 1,2-dichloroethane, and 0.3 g of catalyst, and heat to reflux while stirring, and continue Stir for 10h, stop heating, and the reaction ends. The reaction solution was filtered while it was hot, and after the solid catalyst was separated, the filtrate was decompressed to remove the solvent, cooled to room temperature, and allowed to stand for 10 hours, and the solid was precipitated by filtration to obtain the target product 1,3,5-triacetylhexahydro-s-triazine, yield was 96.3%.

[0037] Structure Identification

[0038] Molecular formula: C 9 h 15 N 3 o 3

[0039] Elemental analysis: theoretical value: C 50.70 H 7.042 N 19.72;

[0040] Found: C 50.61 H 7.031 N 19.61.

[0041] Proton NMR spectrum: δ: 2.15 (s, 9H) 5.23 (s, 6H).

[...

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Abstract

The invention discloses a synthesis method of 1,3,5-tri-substituted perhydro-s-triazine, which aims at solving the problem that the yield of the 1,3,5-tri-substituted perhydro-s-triazine is not high. The synthesis method comprises the following steps of: adding formal, organic nitrile, 30mL to 100mL of 1,2-dichloroethane and 0.1g to 5g of catalyst into a three-mouth flask, wherein the mol ratio between the organic nitrile and the formal is 3.5 to 5: 1; heating in a stirring state till reaction liquid reflows, continuously stirring for 2h to 20h, stopping heating and ending the reaction; decompressing filtrate and removing solvent after the catalyst is separated out by filtering the reaction liquid while hot, standing for 10h to 12h at the room temperature, and filtering to obtain the 1,3,5-tri-substituted perhydro-s-triazine. The invention is mainly used for synthesizing the 1,3,5-tri-substituted perhydro-s-triazine.

Description

technical field [0001] The invention relates to a synthesis method of 1,3,5-trisubstituted hexahydro-s-triazine. technical background [0002] 1,3,5-Trisubstituted hexahydro-s-triazine is an important chemical intermediate, which is mainly used in the fields of polymer reinforcement additives, fungicides, and explosives. [0003] The current synthesis method of 1,3,5-trisubstituted hexahydro-s-triazine uses organic nitrile and paraformaldehyde as raw materials, and reacts in the presence of acidic catalyst concentrated sulfuric acid. For example US3736320 discloses a kind of synthetic method of 1,3,5-triacryloyl hexahydro-s-triazine, the method takes acrylonitrile and paraformaldehyde as raw material, acetic anhydride is water removing agent, concentrated sulfuric acid is catalyst, benzene As a solvent, heated to reflux, reacted for 3 hours, and obtained 1,3,5-triacryloyl hexahydro-s-triazine through post-processing steps, and the yield was 68%. However, the yield of 1,3,5...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/04
Inventor 吕剑杨建明余秦伟刘波李凤仙谷玉杰
Owner XIAN MODERN CHEM RES INST
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