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Preparation method of 2, 3, 5, 6-pyrazinetetranitrile

A technology of pyrazine tetranitrile and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of waste of trifluoroacetic acid and chloroform, high toxicity of benzene and chloroform, great harm to human body, etc., achieve mild reaction conditions, no pollution to the environment, and produce The effect of high purity and yield

Pending Publication Date: 2022-01-21
ZHONGBEI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the disadvantage of the method is that the process uses a variety of drugs such as trifluoroacetic acid, water, chloroform, and benzene for reaction treatment. The waste of drugs such as trifluoroacetic acid and chloroform is serious, and benzene and chloroform are more toxic, which is more harmful to the human body and takes a long time to react. The steps are cumbersome

Method used

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  • Preparation method of 2, 3, 5, 6-pyrazinetetranitrile
  • Preparation method of 2, 3, 5, 6-pyrazinetetranitrile
  • Preparation method of 2, 3, 5, 6-pyrazinetetranitrile

Examples

Experimental program
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Embodiment 1

[0038] Take 2.16g (0.02mol) of 2,3-diamino-2-butenedinitrile, 2.27g (0.01mol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone for later use, and prepare 27mL Add 2,3-diamino-2-butenedinitrile and 2,3-diamino-2-butenedinitrile and 2,3- Dichloro-5,6-dicyano-p-benzoquinone, first dissolve 2,3-diamino-2-butenedinitrile in anhydrous acetic acid, and then add 2,3-dichloro-5, 6-dicyano-p-benzoquinone, add 0.3g each time, each interval is 5min, after the addition is completed, stir and react at room temperature for 2 hours, then raise the temperature of the water bath to 70°C and stir for 2 hours, stop stirring and cool down to room temperature, filter , wash the filter cake with water (15mL*3 times), put the filter cake into a round bottom beaker with a reflux condenser, add 27mL of toluene, heat to 90°C and stir for 30min, filter with filter paper and collect the filtrate, repeat this operation for 5 Second, the pure 2,3,5,6-pyrazinetetranitrile was obtained as a white solid after rotar...

Embodiment 2

[0047] Take 3.24g (0.03mol) of 2,3-diamino-2-butenedinitrile and 2.27g (0.01mol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone for later use, and prepare 35mL Add 2,3-diamino-2-butenedinitrile and 2,3-diamino-2-butenedinitrile and 2,3- Dichloro-5,6-dicyano-p-benzoquinone, first dissolve 2,3-diamino-2-butenedinitrile in anhydrous acetic acid, and then add 2,3-dichloro-5, 6-dicyano-p-benzoquinone, 0.3g each time, each interval is 5min. After the addition is completed, stir and react at room temperature for 2 hours, then raise the temperature of the water bath to 70°C and stir for 2 hours, stop stirring and cool down to room temperature, then filter. Wash the filter cake with water (15mL*3 times), put the filter cake into a round bottom beaker with a reflux condenser, add 32mL of toluene, heat to 90°C and stir for 30min, filter with filter paper and collect the filtrate, repeat this operation 4 times , the pure 2,3,5,6-pyrazinetetranitrile was obtained as a white solid after rotary...

Embodiment 3

[0049] Take 2.16g (0.02mol) of 2,3-diamino-2-butenedinitrile and 2.27g (0.01mol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone for subsequent use, and prepare 20mL Add 2,3-diamino-2-butenedinitrile and 2,3-diamino-2-butenedinitrile and 2,3- Dichloro-5,6-dicyano-p-benzoquinone, first dissolve 2,3-diamino-2-butenedinitrile in anhydrous acetic acid, and then add 2,3-dichloro-5, 6-Dicyano-p-benzoquinone, 0.3g each time, 7min each time, after the addition is completed, stir and react at room temperature for 1.5 hours, then raise the temperature of the water bath to 70°C and stir for 2 hours, stop stirring and cool down to room temperature, filter, Wash the filter cake with water (15mL*3 times), put the filter cake into a round bottom beaker with a reflux condenser, add 27mL of toluene, heat to 90°C and stir for 30min, filter with filter paper and collect the filtrate, repeat this operation 5 times , the pure 2,3,5,6-pyrazinetetranitrile was obtained as a white solid after rotary evap...

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Abstract

The invention discloses a preparation method of 2, 3, 5, 6-pyrazinetetranitrile, and belongs to the technical field of organic synthesis. The 2, 3, 5, 6-pyrazinetetranitrile is subjected to oxidative condensation reaction, a one-step synthesis method is adopted, 2, 3-diamino-2-butene dinitrile is used as a raw material, the raw material is easy to obtain, anhydrous acetic acid is used as a solvent, 2, 3-dichloro-5, 6-dicyanobenzoquinone is used as an oxidizing agent, the 2, 3-diamino-2-butene dinitrile and the 2, 3-dichloro-5, 6-dicyanobenzoquinone are added into the anhydrous acetic acid in batches in the preparation process, anhydrous acetic acid and methylbenzene can replace trifluoroacetic acid to serve as a solvent and a washing treatment product respectively, use and waste of the trifluoroacetic acid raw material are reduced, the cost is saved, the synthesis process is simple, the product purity is high, and no pollution is caused to the environment.

Description

technical field [0001] The invention relates to a preparation method of 2,3,5,6-pyrazine tetranitrile, which belongs to the technical field of organic synthesis. Background technique [0002] 2,3,5,6-pyrazine tetracarbonitrile (TCP) is a typical nitrogen heterocyclic compound with the following structural formula: [0003] [0004] The compound has a good application prospect. [0005] Webster O W etc. (Hydrogen cyanide chemistry.III.Synthesis of diiminosuccinonitrile and its conversion to diaminosuccinonitrile[J].J ORGCHEM,1972,37(25):4133-4136.) and Hartter D R etc. (Hydrogen cyanide chemistry.VII.Diiminosuccinonitrole with diaminomaleonitrile[J].J ORG CHEM,1974,39(9):1235-1239.) proposed a method for preparing 2,3,5,6-pyrazine tetranitrile (TCP), using diiminobutadiene Nitrile (DISN) and 2,3-diamino-2-butenedinitrile (DMAN) were directly condensed in trifluoroacetic acid (TFA) to obtain 2,3,5,6-pyrazine tetranitrile (TCP), yield was 59%. But this method must prepar...

Claims

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Application Information

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IPC IPC(8): C07D241/24
CPCC07D241/24
Inventor 李永祥李军刘文东陈静王小军刘永政张帅曹端林王建龙张璇张广源阮建王娜赵林秀刘明王艳红陈丽珍任福德陈芳
Owner ZHONGBEI UNIV