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Tetramine monomer containing spiro structure, preparation method and application of tetramine monomer, and polyamide and preparation and application thereof

A technology of spiro ring structure and polyamide, which is applied in the field of polyamide and its preparation and application, can solve the problems of low gas permeability coefficient, unfavorable gas separation, and high molecular chain rigidity, so as to improve permeability, improve poor solubility, increase The effect of penetration

Active Publication Date: 2020-07-14
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, for aromatic polyamides with higher rigidity, higher symmetry and stronger intermolecular forces, the free volume of the molecular chain is small, and the gas permeability coefficient is low, which is not conducive to the separation of gases; It is the focus of people's pursuit and attention to develop gas separation membranes with high separation efficiency, environmental protection, low energy loss, safe operation, long service life and high mechanical properties.
[0003] At present, the main problems of polyamide gas separation membranes are that although they have good selectivity and good processability, they have high molecular chain rigidity, low permeability, poor solubility and mechanical properties.

Method used

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  • Tetramine monomer containing spiro structure, preparation method and application of tetramine monomer, and polyamide and preparation and application thereof
  • Tetramine monomer containing spiro structure, preparation method and application of tetramine monomer, and polyamide and preparation and application thereof
  • Tetramine monomer containing spiro structure, preparation method and application of tetramine monomer, and polyamide and preparation and application thereof

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preparation example Construction

[0049] The present invention provides the preparation method of the tetraamine monomer containing spiro ring structure described in above-mentioned technical scheme, comprises the following steps:

[0050] Mixing the acid solution of acetone and the acid solution of catechol to carry out an addition substitution reaction to obtain a spiro tetraphenol compound;

[0051]Or mix the acid solution of hexafluoroacetone, the acid solution of catechol and the reducing agent, and carry out isomerization reaction to obtain the spirotetraphenol compound;

[0052] Mixing the spirotetraphenol compound, chloramide compound, catalyst and reaction solvent, and performing a nucleophilic substitution reaction to obtain a tetraamine monomer;

[0053] The structure of the chloramide compound is Cl-R 3 -NH 2 , where R 3 for

[0054] In the present invention, unless otherwise specified, the required preparation materials are commercially available products well known in the art.

[0055] The...

Embodiment 1

[0100] The preparation of spiro tetraphenol compound:

[0101] The 1.071mL HI aqueous solution that the mass content is 99% is added in the acetone of 5.3535g (0.092mol) to form the acid solution of acetone (the concentration of acetone is 5.0g / mL), and it is added to containing 25.3253g (0.23mol) In 76.74mL of catechol in acetic acid aqueous solution (the concentration of acetic acid aqueous solution is 99.5%), so that the concentration of catechol is 0.33g / mL, the resulting mixed solution is heated to reflux at 120°C for 10h, and then cooled to room temperature to obtain Supersaturated solution, the obtained supersaturated solution is utilized hydrothermal crystallization method, at 220 ℃, 0.3GPa high temperature and high pressure, precipitates white microcrystalline compound, filters, washes three times alternately with glacial acetic acid, dichloromethane to obtain 18.0432g (0.053mol ) spirocyclic tetraphenol compound, the product structure that obtains is as follows:

[...

Embodiment 2

[0107] Preparation of spirocyclic polyfluorotetraphenol compounds:

[0108] The HI aqueous solution that 1.40mL mass concentration is 99% is joined in the hexafluoroacetone of 7.32g (0.044mol) and forms the acid solution of hexafluoroacetone (the concentration of hexafluoroacetone is 5.23g / mL), the mixed solution that forms is added into In the aqueous acetic acid solution containing 12.11g (0.11mol) catechol (the concentration of acetic acid aqueous solution is 99.5%), make the concentration of catechol be 0.4g / mL, then dropwise add 12g (0.24mol) of catechol Hydrazine hydrate, the obtained solution was heated to reflux at 120°C for 10h, then cooled to room temperature to obtain a supersaturated solution, and the reaction was continued for 2h, and the obtained supersaturated solution was subjected to hydrothermal crystallization to precipitate a white micro Crystalline compound, filter, alternately wash three times with glacial acetic acid, dichloromethane to obtain the spiroc...

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Abstract

The invention provides a tetramine monomer containing a spiro structure and a preparation method and application thereof, and polyamide and preparation and application thereof, and belongs to the technical field of gas membrane separation. According to the invention, a spiro center in a microporous polymer (PIMs) is introduced into a tetramine monomer, so that the tetramine monomer containing an aliphatic group (methylene) and having a microporous structure can be obtained. The polyamide film prepared from the tetramine monomer has the characteristics of high gas selectivity, high permeability, good solubility, good selectivity and the like, also has excellent thermal properties, and can be used as a novel polyamide gas separation film.

Description

technical field [0001] The invention relates to the technical field of gas membrane separation, in particular to a tetraamine monomer containing a spiro ring structure and its preparation method and application, polyamide and its preparation and application. Background technique [0002] Membrane separation technology is one of the emerging technologies with the most development potential since the 21st century. Compared with traditional separation methods, it has the advantages of high efficiency, environmental protection, simple and flexible operation, etc. It is widely used in natural gas, hydrogen, nitrogen, oxygen, carbon dioxide and other gases. separation aspect. In terms of the selection of membrane separation materials, polymer membrane materials have attracted extensive attention because of their better processability. Polyamide has the advantages of excellent comprehensive properties, outstanding mechanical properties, good thermal stability, outstanding flame re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/06C07C231/12C08G69/28C08G69/32C08G69/42
CPCC07C235/06C08G69/28C08G69/32C08G69/42
Inventor 陈春海王书丽李莉姚佳楠周宏伟赵晓刚
Owner JILIN UNIV
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