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Method for preparing hydrogen by promoting dehydrogenation of nitrogen heterocyclic compound through alkali

A nitrogen heterocyclic compound, dehydrogenation technology, applied in chemical instruments and methods, hydrogen, inorganic chemistry and other directions, can solve problems such as increasing the reaction cost, and achieve the effects of simple operation, wide application range and high reaction efficiency

Active Publication Date: 2020-06-19
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is commonly used as an organometallic catalyst, which increases the reaction cost to a certain extent.

Method used

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  • Method for preparing hydrogen by promoting dehydrogenation of nitrogen heterocyclic compound through alkali
  • Method for preparing hydrogen by promoting dehydrogenation of nitrogen heterocyclic compound through alkali
  • Method for preparing hydrogen by promoting dehydrogenation of nitrogen heterocyclic compound through alkali

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] The specific process is: Weigh the saturated six-membered nitrogen heterocyclic compound 1a (0.5mmol), base tBuOK (1.5mmol), add to a 25mL reaction tube with a branch, after nitrogen replacement, add 2mL o-xylene, put The reaction was carried out in an oil bath at 140°C for 36 hours, and the hydrogen gas generated during the reaction was collected by a balloon. After the reaction is complete, cool to room temperature, filter with diatomaceous earth, and rotate under reduced pressure to remove the solvent, and then use silica gel column chromatography (eluent is petroleum ether (60-90°C) / ethyl acetate: 4:1, v / v), the light yellow liquid product 2a (59 mg, yield 90%) was obtained. The target product was confirmed by NMR spectroscopy. The generation of hydrogen gas was detected by gas phase, with CH 4 As an internal standard, 19.1 mL of hydrogen gas was generated.

Embodiment 2

[0035] The reaction steps and operations are the same as in Example 1, except that the base tBuONa (1.5 mmol) is added to the reaction system. The reaction was stopped, and the target product 2a (51 mg, yield 76%) was obtained as a light yellow liquid after post-processing. The generation of hydrogen gas was detected by gas phase, with CH 4 As an internal standard, generate 15.7mL of hydrogen gas.

Embodiment 3

[0037] The reaction steps and operations are the same as in Example 1, except that the base tBuOLi (1.5 mmol) is added to the reaction system. The reaction was stopped, and the target product 2a (46 mg, yield 70%) was obtained as a light yellow liquid after post-processing. The generation of hydrogen gas was detected by gas phase, with CH 4 As an internal standard, 14.6 mL of hydrogen gas was generated.

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Abstract

The invention discloses a method for preparing hydrogen by alkali-promoted nitrogen heterocyclic dehydrogenation. According to the method, hydrogen is prepared by using indoline, 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroquinoxaline as initial raw materials under the action of a cheap and easily available alkali while indole, quinoline and quinoxaline compounds are obtained. The method hasthe advantages of accessible raw materials, high reaction efficiency and diversified functional groups, and is simple to operate.

Description

technical field [0001] The invention relates to a method for preparing hydrogen by promoting dehydrogenation of nitrogen heterocyclic compounds with alkali. Background technique [0002] With the increasing emphasis on environmental protection, people are paying more and more attention to finding ways to replace fossil energy. However, new energy sources to replace fossil energy sources are still being explored. As a possible alternative, hydrogen energy has the advantages of high energy density and clean emissions. Therefore, exploring hydrogen storage methods has important industrial application prospects. [0003] Conventional methods for hydrogen storage and transportation at this stage include high-pressure gaseous hydrogen storage, low-temperature liquid hydrogen storage, and hydrogen storage alloys. New hydrogen storage methods include inorganic hydrogen storage, organic hydrogen storage, and other new materials. Inorganic hydrogen storage is the principle of hydr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C01B3/22
CPCC01B3/22
Inventor 余正坤刘婷婷
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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