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Synthetic method of aromatic aziridine cross-linking agent

A technology of aziridine crosslinking agent and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of increased waste discharge, cumbersome sulfate ester synthesis process, and increased risk, so as to save energy and cost and have a good industrialization prospect , the effect of reducing risk

Inactive Publication Date: 2020-11-20
HUNAN CHANGLING PETROCHEM SCI & TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The technical problem that the present invention mainly solves is to provide a kind of synthetic method of aromatic aziridine cross-linking agent, to solve the synthetic process of sulfuric acid ester existing in the existing method is loaded down with trivial details, the synthesis of 2-methyl aziridine, separation and It is discontinuous with the subsequent reaction process, which brings problems such as increased process complexity and risk, increased waste discharge, and reduced product yield.

Method used

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  • Synthetic method of aromatic aziridine cross-linking agent
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  • Synthetic method of aromatic aziridine cross-linking agent

Examples

Experimental program
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Embodiment 1

[0030] [Example 1] The structural design of the synthetic reactor of aminoisopropylsulfate

[0031] The structure of the reactor for the synthesis of aminoisopropyl sulfate refers to the attached image 3 . Among them, 1-diluted chlorosulfonic acid storage tank, 2-feed pump, 3-nitrogen inlet, 4-stirring motor, 5-jacketed reactor, 6-front protection tank, 7-acid mist absorption tank , 8-rear protection tank, 9-vacuum regulating valve, 10-vacuum inlet.

Embodiment 2

[0032] [embodiment 2] the synthesis of amino isopropyl sulfate

[0033] Transfer 150.0g of 1-amino-2-propanol and 1000mL of diethyl ether into the reactor, start stirring to make them fully mixed. Put in a circulating water bath to cool the system temperature to about 8°C, and at the same time, mix 233.0g of chlorosulfonic acid and 500mL of diethyl ether evenly and transfer it to a liquid storage tank for use; blow nitrogen into the reactor and adjust the vacuum to -0.008MPa; Slowly pump the diluted chlorosulfonic acid solution into the reactor with vigorous stirring, and maintain the stability of the system temperature by adjusting the feeding speed; after the feeding is completed, maintain the temperature and continue to stir for 0.5h; after the reaction, filter the reaction solution The insoluble matter was collected and fully rinsed with ether; after vacuum drying, 283.2 g of white powder product aminoisopropyl sulfate was obtained, with a yield of 85.4%.

Embodiment 3

[0034] [embodiment 3] the synthesis of amino isopropyl sulfate

[0035] Transfer 132.0g of 1-amino-2-propanol and 1000mL of cyclohexane into the reactor, start stirring to make them fully mixed. Pass through a circulating water bath to cool the system temperature to about 4°C. At the same time, mix 209.0g of chlorosulfonic acid and 500mL of cyclohexane evenly and transfer it to a liquid storage tank for use; pass nitrogen into the reactor and adjust the vacuum to -0.014 MPa; slowly pump the diluted chlorosulfonic acid solution into the reactor with vigorous stirring, and maintain the stability of the system temperature by adjusting the feeding speed; after the feeding is completed, keep the temperature and continue to stir for 1h; The insoluble matter was collected by filtration and fully rinsed with cyclohexane; after vacuum drying, 285.4 g of white powder product aminoisopropyl sulfate was obtained, with a yield of 92.0%.

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Abstract

The invention discloses a synthetic method of an aromatic aziridine cross-linking agent (figure 1). The method comprises three chemical synthesis steps: (I) reacting 1-amino-2-propanol with chlorosulfonic acid to obtain amino-isopropyl sulfate; (II) carrying out an intra-molecular nucleophilic substitution reaction on amino-isopropyl sulfate in alkali liquor, removing sulfate radical groups, and carrying out ring closing to generate an intermediate 2-methyl aziridine; and (III) directly reacting the obtained 2-methyl aziridine with isophthaloyl dichloride in a mixed system of alkali liquor andan organic solvent without separation, and carrying out separation and purification to obtain a final product 1,1'-(1,3-phthaloyl)bis(2-methyl-aziridine). The commodity name is HX-752, and the aromatic aziridine cross-linking agent has wide application. A liquid-liquid homogeneous or heterogeneous reaction is adopted, the reaction conditions are mild, the process is simple and easy to control, and the yield is high. Besides, the synthesis method has the advantages of fewer byproducts and low waste discharge amount, is suitable for large-scale production, and has favorable industrialization prospects.

Description

technical field [0001] The invention relates to the field of synthesis of multifunctional aziridine compounds, in particular to a synthesis method of an aromatic aziridine crosslinking agent. Background technique [0002] Aziridine is the simplest saturated three-membered azacyclic ring with high ring tension and a strong tendency to break the C-N bond in the structure, so that the aziridine ring has high reactivity and is easy to be attacked by protons to open the ring , can react with groups containing active hydrogen such as carboxyl, hydroxyl and amino groups. Aziridine cross-linking agent is a kind of compound containing binary or multi-component aziridine group in molecular structure. Generally, it can react with carboxyl group at room temperature. Under acidic conditions (pH<6), it can also It can react with hydroxyl or amino groups, and its reactivity gradually increases with the increase of temperature. It has the characteristics of fast reaction rate, less dosa...

Claims

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Application Information

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IPC IPC(8): C07D203/18C08K5/3412
CPCC07D203/18C08K5/3412
Inventor 陈栋王波黄华姚飞沈鹏飞田娟谢琼玉佘喜春
Owner HUNAN CHANGLING PETROCHEM SCI & TECH DEV CO LTD
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