Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof

A technology of distyrylbenzene and trinitro, which is applied in the preparation of organic compounds, aromatic nitration compositions, organic chemistry, etc., can solve the problems of difficult temperature control and compound decomposition, and achieve wide absorption band and good optics The effect of the characteristic

Inactive Publication Date: 2014-09-03
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

(K.M. Poulsen, T. Reenberg, T. andJ.B.Christensen,Synth.Commun.2004,34,2215;S.SaravananandP.C.Srinivasan,Synth.Commun.2001,31,823) However, polynitro compounds have a certain

Method used

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  • Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof
  • Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof
  • Chlorinated 2, 4, 6-trinitro-1, 3- distyryl benzene derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 2,4,6-Trinitro-1,3-bis(4’-chlorostyryl)benzene (R 1 , R 2 is a hydrogen atom, R 3 for chlorine atom) microwave synthesis:

[0027] Mix and dissolve 0.48g (2.0mmol) of 2,4,6-trinitro-m-xylene and 0.59g (4.2mmol) of p-chlorobenzaldehyde in 20mL of dichloromethane, add dropwise 0.08g (0.9mmol) of piperidine and Carrier silica gel (3.0g), the raw material and basic catalyst are evenly loaded on the carrier, and the solvent is removed under normal pressure to obtain a solid mixture of loaded raw materials. After mixing uniformly, the obtained solid is transferred to a Pyrex reaction bottle and exposed to microwave In the reactor, take it out after 15 minutes of microwave under 300W power. After the reaction is finished, the product is extracted with acetone, and then the acetone is removed to obtain a crude product, which is finally recrystallized with a mixed solvent of acetone and ethanol. The title compound (0.75 g) was obtained in a yield of 77%.

[0028] Yellow cry...

Embodiment 2

[0033] 2,4,6-Trinitro-1,3-bis(2’-chlorostyryl)benzene (R 2 , R 3 is a hydrogen atom, R 1 for chlorine atom) microwave synthesis:

[0034] Mix and dissolve 0.48g (2.0mmol) of 2,4,6-trinitro-m-xylene and 0.59g (4.2mmol) of o-chlorobenzaldehyde in 20mL of dichloromethane, add dropwise 0.08g (0.9mmol) of piperidine and The carrier NaOH (3.0g), the raw material and the basic catalyst are evenly loaded on the carrier, and the solvent is removed under normal pressure to obtain a solid mixture of loaded raw materials. After mixing evenly, the obtained solid is transferred to a Pyrex reaction bottle and placed in a microwave oven. In the reactor, take it out after 15 minutes of microwave under 300W power. After the reaction is finished, the product is extracted with acetone, and then the acetone is removed to obtain a crude product, which is finally recrystallized with a mixed solvent of acetone and ethanol. The title compound (0.88 g) was obtained with a yield of 85.7%.

[0035] ...

Embodiment 3

[0040] 2,4,6-Trinitro-1,3-bis(2’,4’-dichlorostyryl)benzene (R 1 , R 3 is chlorine, R 2 for the microwave synthesis of hydrogen atoms):

[0041] Mix and dissolve 0.48g (2.0mmol) of 2,4,6-trinitro-m-xylene and 2,4-dichlorobenzaldehyde (0.70g, 4.2mmol) in 20mL of dichloromethane, add dropwise morpholine and carrier Potassium carbonate (3.0g), the raw material and the basic catalyst are evenly loaded on the carrier, and the solvent is removed under normal pressure to obtain a solid mixture of loaded raw materials. After mixing uniformly, the obtained solid is transferred to a Pyrex reaction bottle and placed in a microwave In the reactor, take it out after 15 minutes of microwave under 300W power. After the reaction is finished, the product is extracted with acetone, and then the acetone is removed to obtain a crude product, which is finally recrystallized with a mixed solvent of acetone and ethanol. The title compound (0.90 g) was obtained with a yield of 81.1%.

[0042] Yel...

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Abstract

The invention discloses 2, 4, 6-trinitro-1, 3-distyryl benzene derivatives containing chlorine substituent as well as a preparation method and an application thereof. The chemical structure of the compounds is characterized in that three nitryls exist at positions 2, 4, 6 of a middle benzene ring of 1, 3-distyryl benzene, and ortho-positions, meta-positions and para-positions of benzene rings at the two sides are connected to chlorine atoms, or the ortho-positions and the para-positions are simultaneously connected to the chlorine atoms. The chemical structure of the compounds is confirmed to be the trans-structure when the coupling constant of diphenylethene double bonds in a nuclear magnetic resonance spectrum is about 16.0Hz. The 2, 4, 6-trinitro-1, 3-distyryl benzene derivatives containing chlorine substituent are synthesized through microwave assistance under a catalysis condition, are simple in a preparation technology, solvent-free, fast, green and safe and can be potentially applied to the field of luminescent devices and energetic materials.

Description

technical field [0001] The invention belongs to the field of energetic materials and organic luminescence, and specifically relates to a 2,4,6-trinitro-1,3-distyrylbenzene derivative containing a chlorine substituent, its preparation and application. Background technique [0002] The conjugation effect between the double bond and the benzene ring in the structure of stilbene compounds makes the chemical properties of these compounds relatively stable. The polynitrostilbene compound is a very important chemical intermediate, which can be widely used in the fields of nonlinear optics and high-energy heat-resistant energetic materials. For example, it can be used to synthesize new ligands for nonlinear optical materials and heat-resistant explosives for military and civilian use. Among them, hexanitrostilbene (HNS) with outstanding performance is one of the polynitrostilbene compounds. It is a yellow crystal with a melting point as high as 317°C. It is a heat-resistant explosi...

Claims

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Application Information

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IPC IPC(8): C07C205/12C07C201/12C06B25/04C09K11/06
Inventor 彭新华徐俊辉魏建平李芳美
Owner NANJING UNIV OF SCI & TECH
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