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A method for synthesizing n-(ethoxymethylene)aniline with styrene-styrenesulfonic acid copolymer microspheres as catalyst

A technology of styrene sulfonic acid and sodium styrene sulfonate, which is applied in the field of solid acid catalysis, can solve the problems of cumbersome catalyst separation process, difficult separation and recycling, low catalytic activity, etc., and achieves reduction of pollutant discharge and high yield , Improve the effect of product purity

Active Publication Date: 2017-12-22
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] h 2 SO 4 , HCl and other liquid acid catalysts are widely used in the synthesis of N-(ethoxymethylene)aniline, but the selectivity is not high, and a large amount of N,N'-benzamidine is often produced, and the reaction process needs to remove water. Moreover, the catalyst separation process is cumbersome, and there are also corrosion problems
p-toluenesulfonic acid is a solid acid, no need to remove water during the reaction, but it is a homogeneous acid, soluble in the reaction system during the reaction, difficult to separate and recycle
Therefore, in recent years, people have begun to study the application of recyclable solid acid catalysts in the synthesis of N-(ethoxymethylene)aniline, such as: H-ZSM-5, MCM-41, but their catalytic activity is low, Can only reach 77%~84%

Method used

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  • A method for synthesizing n-(ethoxymethylene)aniline with styrene-styrenesulfonic acid copolymer microspheres as catalyst
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Experimental program
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Effect test

Embodiment 1

[0025] (1) In the round-bottomed flask with a condenser tube and a thermometer, nitrogen gas was introduced in advance for 15 minutes. Under the protection of nitrogen gas, the constant temperature water bath was heated to 60 ° C, and 20 g of styrene, 50 mL of deionized water, 0.025 g of sodium hydroxide, 0.021 g of sodium bicarbonate, heated and stirred; when the temperature of the system reached 75°C, 0.28g of potassium persulfate was added, and the system became a milky white liquid, and reacted at this temperature for 3 hours to obtain polystyrene microspheres PS;

[0026] (2) Add 2g of sodium styrene sulfonate to the reaction solution at 75°C in step (1), and continue the reaction for 3 hours; filter and dry to obtain a white solid, that is, styrene-sodium styrene sulfonate copolymer microspheres PS- NaSS@PS;

[0027] (3) The styrene-styrene sodium sulfonate copolymer microspheres PS-NaSS@PS obtained in step (2) were acidified with 4.9ml hydrochloric acid (2mol / L), then w...

Embodiment 2

[0032] (1) In the round-bottomed flask with a condenser tube and a thermometer, nitrogen gas was introduced in advance for 15 minutes. Under the protection of nitrogen gas, the constant temperature water bath was heated to 60 ° C, and 20 g of styrene, 50 mL of deionized water, 0.025 g of sodium hydroxide, 0.021 g of sodium bicarbonate, heated and stirred; when the temperature of the system reached 75°C, 0.8 g of potassium persulfate was added, and the system became a milky white liquid, and reacted at this temperature for 5 hours to obtain polystyrene microspheres PS;

[0033] (2) Add 5g of sodium styrene sulfonate to the reaction solution at 75°C in step (1), and continue the reaction for 3 hours; filter and dry to obtain a white solid, that is, styrene-sodium styrene sulfonate copolymer microspheres PS- NaSS@PS;

[0034] (3) The styrene-styrene sodium sulfonate copolymer microspheres PS-NaSS@PS obtained in step (2) were acidified with 12.1ml hydrochloric acid (2mol / L), then ...

Embodiment 3

[0039](1) In the round-bottomed flask with a condenser tube and a thermometer, nitrogen gas was introduced in advance for 15 minutes. Under the protection of nitrogen gas, the constant temperature water bath was heated to 60 ° C, and 20 g of styrene, 50 mL of deionized water, 0.025 g of sodium hydroxide, 0.021 g sodium bicarbonate, heat and stir; when the temperature of the system reaches 75°C, add 1.4g potassium persulfate, the system becomes a milky white liquid, and react at this temperature for 4 hours to obtain polystyrene microspheres PS;

[0040] (2) Add 8g of sodium styrene sulfonate to the reaction solution at 75°C in step (1), and continue the reaction for 3 hours; filter and dry to obtain a white solid, namely, styrene-sodium styrene sulfonate copolymer microspheres PS- NaSS@PS;

[0041] (3) The styrene-styrene sodium sulfonate copolymer microspheres PS-NaSS@PS obtained in step (2) were acidified with 19.4ml hydrochloric acid (2mol / L), then washed with water, and dr...

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Abstract

The invention relates to a method for synthesizing N-(ethoxymethylene)aniline by using styrene-styrene sulfonic acid copolymer microspheres as a catalyst. In the present invention, the polymerization of styrene is first carried out by soap-free emulsion polymerization to obtain polystyrene PS; then sodium styrene sulfonate NaSS is added to continue soap-free emulsion polymerization to obtain styrene-sodium styrene sulfonate with a core-shell structure Copolymer microspheres PS‑NaSS@PS; then acidified to obtain styrene‑styrene sulfonic acid copolymer microspheres PS‑HSS@PS; using the obtained styrene‑styrene sulfonic acid copolymer microspheres PS‑HSS@ PS as a catalyst for the synthesis of N‑(ethoxymethylene)aniline. The catalyst has a good catalytic effect, can not only improve the product purity, but also realize the recovery and reuse of the catalyst, which is beneficial to reducing pollutant discharge, saving resources and reducing production costs.

Description

technical field [0001] The invention belongs to the technical field of solid acid catalysis, and in particular relates to a method for synthesizing N-(ethoxymethylene)aniline by using styrene-styrene sulfonic acid copolymer microspheres as a catalyst. Background technique [0002] As an important organic chemical raw material, N-(ethoxymethylene)aniline and its derivatives are widely used in pharmaceutical, pesticide, dyestuff and other industries. At present, N-(ethoxymethylene)aniline is mainly synthesized by reacting aniline with triethyl orthoformate. The reaction of aniline and triethyl orthoformate is divided into two steps: the first step is to generate N,N'-benzamidine, and the second step is to generate N-(ethoxymethylene)aniline. These two steps are reversible reactions. In the first step, the reaction of aniline and triethyl orthoformate to generate N,N'-dibenzamidine does not require acid catalysis, and in the second step, N,N'-dibenzamide and The reaction of t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C257/06B01J31/06B01J35/08
CPCC07C257/06B01J31/063B01J2231/4283B01J35/51B01J35/40Y02P20/584
Inventor 刘少杰杜慧丽崔笑菲邢玉彬赵风清
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY