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Ferrocene tetrazole ionic compounds and preparation method thereof

A technology for ferrocene tetrazolium and ionic compounds, which is applied in the field of ferrocene tetrazolium ionic compounds and their preparation, can solve the problem that the catalytic effect is not very good, the iron content of the catalyst is low, and the mechanical properties and technological properties cannot be obtained. and combustion performance, etc., to achieve the effects of low synthesis cost, good thermal stability and non-volatile

Inactive Publication Date: 2015-09-02
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this catalyst contains low iron content and introduces non-energy silicon oxide, so the catalytic effect is not very good.
In addition, people have introduced reactive functional groups such as oxirane, mercapto, and aza groups into ferrocene compounds, and through testing these compounds in solid propellants, they have found that they can partially solve the problem of migration, but none of them can A perfect combination of mechanical properties, process properties and combustion properties

Method used

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  • Ferrocene tetrazole ionic compounds and preparation method thereof
  • Ferrocene tetrazole ionic compounds and preparation method thereof
  • Ferrocene tetrazole ionic compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of ferrocene tetrazolium ion compound with the following structural formula

[0033]

[0034] Completely dissolve 0.232g (0.91mmol) of compound A in a 50mL round-bottomed flask filled with 10mL of absolute ethanol. After the solution is completely transparent, add 0.133g (0.76mmol) of 1-methanol dissolved in 10mL of absolute ethanol dropwise. -3-butylimidazolium chloride salt solution, a white precipitate was formed immediately, stirred at room temperature for 6 hours, filtered with suction, the filtrate was spin-dried, dissolved in dichloromethane, filtered, spin-dried, and recrystallized with acetone / ether. Then the filter cake was dried in a vacuum oven at 50° C. for 24 hours to obtain 0.237 g of a ferrocene tetrazolium ion compound with a melting point of 125.2° C. and a yield of 79%.

[0035] The spectral data of the resulting product is: 1 H NMR (400MHz, DMSO) δ (ppm): 9.14 (s, 1H), 7.74 (d, J = 27.4Hz, 2H), 4.68 (t, J = 1.8Hz, 2H), 4.19 (dd, J = 9...

Embodiment 2

[0037] Preparation of ferrocene tetrazolium ion compound with the following structural formula

[0038]

[0039] In Example 1, the 1-methyl-3-butylimidazolium chloride salt used is replaced by equimolar 1-methyl-3-octylimidazolium chloride salt, and other steps are the same as in Example 1 to obtain ferrocene Tetrazolium ion compound 0.252g, its melting point is 99.9°C, and the yield is 74%.

[0040] The spectral data of the resulting product is: 1 H NMR (400MHz, DMSO) δ (ppm): 9.12 (s, 1H), 7.75 (d, J = 18.2Hz, 2H), 4.68 (t, J = 1.8Hz, 2H), 4.34-4.04 (m, 4H ), 3.90(d, J=43.1Hz, 7H), 1.77(s, 2H), 1.25(s, 10H), 0.85(d, J=6.6Hz, 3H); 13 C NMR (400MHz, DMSO) δ (ppm): 158.86, 136.86, 123.72, 122.34, 99.50, 78.04, 68.79, 67.48, 66.66, 48.83, 35.94, 31.14, 29.40, 28.46, 28.32, 25.49, 22.033, 13. (theoretical calculation values ​​in brackets): C% 61.60 (61.61), H% 7.12 (7.19), N% 18.65 (18.74).

Embodiment 3

[0042] Preparation of ferrocene tetrazolium ion compound with the following structural formula

[0043]

[0044] In Example 1, the 1-methyl-3-butylimidazolium chloride salt used is replaced by equimolar 1-methyl-3-dodecylimidazolium chloride salt, and other steps are the same as in Example 1 to obtain two 0.299 g of ferrocene tetrazolium ion compound, its melting point is 83.4°C, and the yield is 78%.

[0045] The spectral data of the resulting product is: 1 H NMR (400MHz, DMSO) δ (ppm): 9.18 (s, 1H), 7.77 (s, 2H), 4.67 (s, 2H), 4.19 (s, 4H), 3.90 (d, J = 38.2Hz, 7H ), 1.76(s, 2H), 1.24(s, 17H), 0.85(s, 3H); 13 C NMR (400MHz, DMSO) δ (ppm): 158.91, 123.70, 122.32, 78.44, 68.76, 67.36, 66.63, 48.84, 31.26, 29.39, 28.98, 28.92, 28.80, 28.67, 28.36, 25.49, 22.06, 13.9 (theoretical calculation values ​​in brackets): C% 64.20 (64.28), H% 7.91 (7.99), N% 16.59 (16.66).

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Abstract

The invention discloses ferrocene tetrazole ionic compounds and a preparation method thereof. The structural formula of the compounds is disclosed in the specification, wherein X<+> represents 1-methyl-3-alkyliminazole cation, 1-methyl-3-allyliminazole cation or 1-alkyl-2,3-dimethyliminazole cation. The synthesis method is simple to operate and low in cost, and overcomes the defects of complex technique, high price, high cost and the like in the synthesis process of the ferrocene and derivatives thereof. The synthesized ferrocene tetrazole ionic compounds have the advantages of low volatility and high heat stability under natural conditions. Due to the introduction of the nitrogen-rich groups, the compounds have higher formation heat and combustion heat. When being used in a solid propellant, the compounds can contribute energies to the solid propellant. The compounds have adjustable catalytic properties, and thus, can satisfy the formula requirements of different types of solid propellants.

Description

technical field [0001] The invention belongs to the technical field of solid propellants, and in particular relates to a class of ferrocene tetrazolium ion compounds and a preparation method thereof. Background technique [0002] Ferrocene and its derivatives, because of their excellent combustion regulation function, have been widely used in strategic and tactical weapon systems as the most important burning rate catalysts of solid propellants (especially composite propellants). Ballistic missiles (including theater, short-range, medium-range, intercontinental ballistic missiles, etc.), airborne tactical missiles, anti-missile high-speed kinetic energy missiles and sea-based mines, torpedoes and other weapons play a huge role. [0003] Due to the problems of easy migration, volatilization, and low-temperature crystallization of the currently used ferrocene-based burning rate catalysts, it has seriously affected the storage life, reliability, and environmental adaptability o...

Claims

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Application Information

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IPC IPC(8): C07F17/02B01J31/22
CPCB01J31/2295B01J2531/842C06D5/00C07F17/02
Inventor 张国防高晓妮赵凤起樊学忠安亭李吉祯邵二莎
Owner SHAANXI NORMAL UNIV
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