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Norbornene zwitterionic monomer and preparation method thereof

A technology of norbornene and zwitterions, which is applied in the field of norbornene compounds, can solve the problems of unstable chemical degradation of matrix membranes, and achieve the effects of less environmental pollution, high reactivity, and mild preparation reaction conditions

Active Publication Date: 2019-03-29
ZHONGBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the current intrinsic amphoteric ion exchange membranes are mostly prepared by irradiation modification. The severe modification conditions will lead to instability or chemical degradation of the matrix membrane.

Method used

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  • Norbornene zwitterionic monomer and preparation method thereof
  • Norbornene zwitterionic monomer and preparation method thereof
  • Norbornene zwitterionic monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Dissolve norbornene diacid anhydride (10.0265g, 61.08mmol) in 100mL of glacial acetic acid, heat to 125°C, add 1,6-hexanediamine (21.2934g, 183.32mmol), and heat to reflux for 3h to obtain a transparent solution .

[0039] The transparent solution obtained above was distilled under reduced pressure to remove glacial acetic acid. After cooling to room temperature, 100 mL of deionized water was added, extracted three times with 100 mL of dichloromethane, and the organic layer was collected and washed three times with 50 mL of deionized water.

[0040] Collect the remaining aqueous layer after extraction and separation, adjust its pH value to 9 with 1 mol / L sodium hydroxide solution, then extract with 1 L dichloromethane three times, and collect the organic layer.

[0041] The organic layers collected twice were combined, anhydrous sodium sulfate was added, dried overnight, and a clear transparent liquid was obtained by filtration. The crude product was obtained after re...

Embodiment 2

[0048] Dissolve norbornene diacid anhydride (10.0265g, 61.08mmol) in 80mL of glacial acetic acid, heat to 130°C, add 1,6-hexanediamine (14.1888g, 122.16mmol), and heat to reflux for 3h to obtain a transparent solution .

[0049] The transparent solution obtained above was distilled under reduced pressure to remove glacial acetic acid. After cooling to room temperature, 80 mL of deionized water was added, extracted three times with 80 mL of dichloromethane, and the organic layer was collected and washed three times with 40 mL of deionized water.

[0050] Collect the remaining aqueous layer after extraction and separation, adjust its pH value to 9 with 0.5 mol / L sodium hydroxide solution, then extract with 800 mL of dichloromethane three times, and collect the organic layer.

[0051] The organic layers collected twice were combined, anhydrous sodium sulfate was added, dried overnight, and a clear transparent liquid was obtained by filtration. The crude product was obtained aft...

Embodiment 3

[0056] Dissolve norbornene diacid anhydride (10.0265g, 61.08mmol) in 100mL of glacial acetic acid, heat to 135°C, add 1,6-hexanediamine (17.7361g, 152.7mmol), and heat to reflux for 4h to obtain a transparent solution .

[0057] The transparent solution obtained above was distilled under reduced pressure to remove glacial acetic acid. After cooling to room temperature, 100 mL of deionized water was added, extracted three times with 100 mL of dichloromethane, and the organic layer was collected and washed three times with 50 mL of deionized water.

[0058] Collect the remaining aqueous layer after extraction and separation, adjust its pH value to 9 with 1 mol / L sodium hydroxide solution, then extract with 1 L dichloromethane three times, and collect the organic layer.

[0059] The organic layers collected twice were combined, anhydrous sodium sulfate was added, dried overnight, and a clear transparent liquid was obtained by filtration. The crude product was obtained after rem...

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Abstract

The invention discloses a norbornene zwitterionic monomer 5-norbornene-2,3-dicarboximide-N-hexyl tertiary ammonium propanesulfonic acid. The norbornene zwitterionic monomer is prepared by taking norbornene dianhydride and 1,6-hexane diamine as raw materials to synthesize an intermediate 5-norbornene-2,3-dicarboximide-N-hexylamine, then carrying out nucleophilic substitution reaction on the intermediate and 1,3-propane sultone and carrying out ring-opening. The prepared norbornene zwitterionic monomercontains quaternary ammonium functional groups and sulfonic acid functional groups at the sametime, can be used for preparing an ion exchange membrane and is applied to a proton exchange membrane fuel cell and an all-vanadium redox battery.

Description

technical field [0001] The invention relates to a norbornene compound, in particular to a norbornene zwitterionic monomer and a preparation method of the ionic monomer. Background technique [0002] Proton exchange membrane is an important component of proton exchange membrane fuel cell (PEMFC) and all-vanadium redox flow battery (VRB), which has the function of separating cathode and anode and transferring protons. [0003] Commercial perfluorosulfonic acid-type proton exchange membranes have excellent electrical conductivity, chemical stability, and mechanical strength. But perfluorosulfonic acid type proton exchange membrane contains hydrophilic groups, when it is used in direct methanol fuel cell (DMFC), it has higher permeability to methanol, and about 40% of methanol will permeate into the cathode; and then, in Under high temperature and low humidity conditions, the conductivity of the exchange membrane will decrease. When the proton exchange membrane is used for VRB...

Claims

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Application Information

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IPC IPC(8): C07D209/76H01M8/103H01M8/1032H01M8/18C08G61/08
CPCC07D209/76C08G61/08C08G2261/11C08G2261/143C08G2261/1452C08G2261/418H01M8/103H01M8/1032H01M8/188Y02E60/50
Inventor 何振峰刘蕾任敬霞王超郭丽
Owner ZHONGBEI UNIV
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