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Electrochemical synthesis method of 2, 2-bissuccinimide derivative

A technology of succinimide and synthesis method, which is applied to electrolytic components, electrolytic processes, electrolytic organic production, etc., can solve the problems of harsh conditions and high price, and achieves the effects of mild reaction conditions, easy operation and reduced material consumption.

Pending Publication Date: 2022-05-27
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional chemical synthesis methods generally need to be carried out step by step, the price of 1,2,3,4-butane tetracarboxylic dianhydride is also relatively expensive, and the reaction needs to be carried out at high temperature, and the conditions are relatively harsh

Method used

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  • Electrochemical synthesis method of 2, 2-bissuccinimide derivative
  • Electrochemical synthesis method of 2, 2-bissuccinimide derivative
  • Electrochemical synthesis method of 2, 2-bissuccinimide derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0055] The synthetic method of N,N'-dibenzyl-2,2'-disuccinimide is as follows:

[0056] Galvanostatic electrolysis with a current density of 20 mA∕cm 2 , a platinum sheet (2cm×2cm) was used as the anode electrode and cathode electrode. In a one-chamber electrolytic cell, the substrate N-benzyl-maleimide (1 mmol) was added, and NaNO was added. 3 (10 mmol) was used as electrolyte, DMF (5 mL) was added as organic solvent, phosphate buffer (15 mL) of pH (6~7) was added, water bath at 40°C was used, and the reaction progress was tracked by thin-layer chromatography. The reaction time was 20 h. . After the reaction, the reaction solution was poured into 300 mL of water, and a white solid was precipitated, which was filtered and dried with a yield of 70%.

[0057] The structural formula of N,N'-dibenzyl-2,2'-disuccinimide is .

Embodiment 2~ Embodiment 15

[0059] Different maleimide derivatives were used as reaction raw materials to synthesize corresponding 2,2'-disuccinimide derivatives, and the experimental parameters and experimental steps were the same as those in Example 1. The experimental results of the examples are shown in Table 1.

[0060]

Embodiment 16- Embodiment 21

[0062] Synthesis of N,N'-dibenzyl-2,2'-disuccinimide with different organic solvents: galvanostatic electrolysis with a current density of 5 mA∕cm 2 , a platinum sheet (2cm×2cm) was used as the anode electrode and cathode electrode. In a one-chamber electrolytic cell, the substrate N-benzyl-maleimide (1 mmol) was added, and NaNO was added. 3 (6 mol) was used as electrolyte, 5 mL of organic solvent was added, phosphate buffer solution (15 mL) of pH (6~7) was added, water bath at 20°C, and the reaction progress was tracked by thin-layer chromatography. The reaction time was 15 h. After the reaction, the reaction solution was poured into 300 mL of water, and a white solid was precipitated, which was filtered and dried. The experimental results of the examples are shown in Table 2.

[0063]

[0064] Comparing Example 16, Example 17, Example 18, Example 19, Example 20 and Example 21, the present invention selects several solvents that are mutually miscible with the aqueous solu...

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Abstract

The invention provides an electrochemical synthesis method of a 2, 2 '-bis-succinimide derivative, which is characterized in that an organic solvent in which a maleimide derivative is dissolved is used as an electrolytic reaction raw material, and the 2, 2'-bis-succinimide derivative is synthesized under an electrolytic condition. Compared with traditional organic synthesis, the electrochemical method for synthesizing the 2, 2 '-bissuccinimide derivative has remarkable advantages, the electrochemical reaction is realized by obtaining and losing electrons from reactants on an electrode, additional reducing agents or metal catalysts are not needed, material consumption is reduced, and therefore environmental pollution is reduced; the reaction can be carried out at room temperature and normal pressure, the reaction condition is mild, and the post-treatment is simple, which is very beneficial to energy conservation and equipment investment reduction; the process flow is simple, the operation is simple and convenient, the reaction is easy to control, and the 2, 2 '-bissuccinimide derivative can be obtained through one-pot reaction; the reaction raw materials are cheap and easily available, and are very safe to use; the reaction process is environment-friendly and meets the requirements of an environment-friendly chemical process.

Description

technical field [0001] The invention belongs to the technical field of electrochemical synthesis, in particular to a method for electrochemical synthesis of 2,2'-disuccinimide derivatives. Background technique [0002] Succinimide has a unique five-membered ring structure, and 2,2'-disuccinimide derivatives have many applications in material production and processing. For example: N,N-bismethyl-2,2'-disuccinimide can be used as a reaction intermediate for the preparation of the structure-directing agent required for the synthesis of porous aluminosilicate EMM-37. In 2009, Akiyama et al. reported that the hardener containing N,N-bis(3-hydroxyphenyl)-2,2'-disuccinimide could increase the glass transition temperature of the epoxy resin prepared by it, and make the epoxy resin more elastic. The modulus is kept at a low level, and the prepared epoxy resin has low internal stress and can be used for encapsulating semiconductor devices. In addition, the 2,2'-bissuccinimide struct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/05C25B3/07C25B3/09C25B3/29
CPCC25B3/05C25B3/07C25B3/09C25B3/29
Inventor 陈万里赵婧朱英红
Owner ZHEJIANG UNIV OF TECH
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