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Fullerene aniline derivatives, preparation method and use thereof

A technology of fullerene aniline and derivatives, which is applied in offensive equipment, organic chemistry, explosives, etc., can solve the problems of poor thermal stability and poor stabilization effect of chemical stabilizers, and achieve stable performance, novel structure and high quality. Effect

Active Publication Date: 2022-04-01
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the disadvantages of poor thermal stability and poor stabilizing effect of the chemical stabilizer in the existing solid rocket propellant, to provide a stabilizer with excellent stabilizing effect and very stable performance and its preparation method

Method used

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  • Fullerene aniline derivatives, preparation method and use thereof
  • Fullerene aniline derivatives, preparation method and use thereof
  • Fullerene aniline derivatives, preparation method and use thereof

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Experimental program
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Effect test

Embodiment 1

[0021] Embodiment 1: Synthesis of hexachlorofullerene with fullerene and iodine monochloride

[0022] Add C to the 250mL flask 60 (0.48g, 0.68mmol) and 80mL of chlorobenzene, ultrasonically make C 60 completely dissolved. At room temperature (25°C), add ICl (1mL, 20.0mmol), C 60 :ICl molar ratio is about 1:30. Then replace the air atmosphere with N 2 system, in N 2 Reaction under atmosphere for 2h. Use a decompression device equipped with a cold trap to evaporate under reduced pressure until there is no solvent, and the process is controlled within 0.5h. Then an appropriate amount of CH 2 Cl 2 Dissolve the orange-red product in the bottle and spin dry to remove a small amount of iodine or iodine monochloride, repeating several times. It was then transferred to a 50 mL flask and spin-dried to obtain an orange-red solid product with a yield of 96%.

Embodiment 2

[0023] Embodiment 2: Preparation of fullerene aniline derivative F1

[0024]

[0025] Weigh hexachlorofullerene (100mg, 0.11mmol) and dissolve it in 100ml toluene, sonicate to C 60 Cl 6 Completely dissolved, it was a transparent orange-red solution, an appropriate amount of aniline (1.1mmol, 100uL) was added, followed by triethylamine (150ul, 1.1mmol), stirred vigorously at room temperature, and reacted for 2h until TLC analysis showed C 60 Cl 6 basically disappeared. The organic phase was washed three times with water and then dried. Toluene was removed by evaporation under reduced pressure to obtain a crude product. Separation and purification by silica gel column chromatography, using toluene-ethyl acetate as the eluent, gradient elution to obtain an orange-red solution, which was spin-dried to obtain an orange-red solid product F1 with a yield of 45%. FT-IR (KBr pellet, v, cm -1 ):3400(N-H),3041(Ar-H),2921,2850,1636,1596,1490,1417(benzene ring),1384,1228(C-N),1196...

Embodiment 3

[0026] Embodiment 3: Preparation of fullerene methylaniline derivative F2

[0027]

[0028] Weigh hexachlorofullerene (100mg, 0.11mmol) and dissolve in 80ml chlorobenzene, sonicate to C 60 Cl 6 Completely dissolved, it was a transparent orange-red solution, an appropriate amount of methylaniline (1.1mmol, 118mg) was added, followed by triethylamine (150ul, 1.1mmol), stirred vigorously at room temperature, and reacted for 2h until TLC analysis showed C 60 Cl 6 basically disappeared. The organic phase was washed three times with water and then dried. Chlorobenzene was removed by evaporation under reduced pressure to obtain a crude product. Separation and purification by silica gel column chromatography, using toluene-ethyl acetate as the eluent, gradient elution to obtain an orange-red solution, which was spin-dried to obtain an orange-red solid product F2 with a yield of 58%. FT-IR (KBr pellet, ν, cm -1):3400(N-H),2918,2852(C-H),1608,1508,1458(benzene ring),1230(C-N),1...

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Abstract

The invention discloses a fullerene aniline derivative represented by formula (I) and a preparation method thereof. First, fullerene and iodine monochloride are used as raw materials to obtain hexachlorofullerene through substitution reaction, and then nucleophilic substitution reaction between hexachlorofullerene and aniline is used to obtain fullerene aniline derivatives. The fullerene derivative can be used as a novel stabilizer in solid rocket propellants. In formula (I), R is -H, -CH 3 ,-OCH 3 ,-C 2 h 5 ,-OC 2 h 5 ,-C 3 h 7 (,-OC 3 h 7 ,-C 4 h 9 ,-C 5 h 11 .

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and relates to a fullerene aniline derivative and a preparation method thereof. The prepared fullerene aniline derivatives can be used as chemical stabilizers in solid rocket propellants. [0002] technical background [0003] With the development of my country's aerospace industry and the continuous improvement of national defense science and technology requirements for high-end weapons, high-performance propellants have become a hot topic of research. Stabilizer is one of the indispensable components to ensure sufficient storage and service life of solid propellants, and is a very critical functional additive in solid propellant formulations. Searching for chemical stabilizers with excellent performance has become the main direction to improve the storage life of propellants under the condition that the main components of existing propellants remain unchanged. [0004] Nitrate-based p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D203/26C06B23/00
CPCC07D203/26C06B23/00
Inventor 金波彭汝芳柴作虎张青春黄琪
Owner SOUTHWEAT UNIV OF SCI & TECH
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