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Synthetic method of tetrahydrotetracyclopentadiene

A technology of tetrahydrocyclopentadiene tetramer and cyclopentadiene tetramer, which is applied in the field of high-density hydrocarbon fuel preparation, can solve the problems of no public reports on the synthesis method, and achieve simple synthesis method and high yield High, wide-source effects

Active Publication Date: 2014-12-24
HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cyclopentadiene polymer compounds are common high-density hydrocarbon fuels, and the density of this type of fuel increases with the increase of cyclopentadiene ring number. It is reported in the literature (Energetic Materials, 2009, 157-160) that tetrahydro The density of cyclopentadiene tetramer is as high as 1.043g / cm 3 , 43.1MJ / L, density and calorific value are higher than hanging tetrahydrodicyclopentadiene (JP-10, density 0.934g / cm 3 , calorific value 39.3MJ / L) increased by 10.9% and 9.2% respectively, it can be seen that tetrahydrocyclopentadiene tetramer has extremely high density and volume calorific value, which can provide more propulsion energy for aircraft, but this type The specific synthesis method of the compound has not yet been published

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Take 100g of cyclopentadiene dissolved in 200g of n-hexane and add it to the autoclave, replace the air in the autoclave with nitrogen three times, fill it with nitrogen to 1Mpa, and react under the conditions of stirring 500 rpm and 180°C for 8 hours, then stop the reaction and drop to room temperature , add 10g of palladium-carbon hydrogenation catalyst with 5% palladium content (mass fraction) into the above reaction system, replace the air in the kettle with nitrogen three times, start stirring at 750 rpm, and hydrogenate under the conditions of hydrogen pressure of 1MPa and temperature of 160°C After reacting for 12 hours, the above-mentioned reactant was filtered to remove the catalyst, the solvent n-hexane was distilled off, a white solid was precipitated by cooling, and recrystallized with ethanol to obtain 31 g of tetrahydrocyclopentadiene tetramer.

Embodiment 2

[0015] Take 100g of cyclopentadiene dissolved in 35g of cyclohexane and add it to the autoclave, replace the air in the autoclave with nitrogen three times, fill it with nitrogen to 2Mpa, stir at 500 rpm, and react for 12 hours at a temperature of 200°C, then stop the reaction. At room temperature, add 15g of palladium-carbon hydrogenation catalyst with 5% palladium content (mass fraction) to the above reactants, replace the air in the kettle with nitrogen for three times, start stirring at 750 rpm, and add hydrogen under the conditions of 2MPa hydrogen pressure and 150°C. After hydrogen reaction for 15 hours, the catalyst was removed by filtration of the reactant, the solvent cyclohexane was distilled off, a white solid was precipitated by cooling, and recrystallized with ethanol to obtain 33 g of tetrahydrocyclopentadiene tetramer.

Embodiment 3

[0017] Take 100g of cyclopentadiene dissolved in 100g of n-pentane and add it to the autoclave, replace the air in the autoclave with nitrogen three times, then fill it with nitrogen to 4Mpa, stir at 500 rpm, and react for 15 hours at a temperature of 230°C, then stop the reaction. At room temperature, add 5g of palladium-carbon hydrogenation catalyst with 10% palladium content (mass fraction) to the above-mentioned reactants, replace the air in the kettle with nitrogen three times, start stirring at 750 rpm, and add hydrogen under the conditions of hydrogen pressure of 4MPa and temperature of 170°C. After hydrogen reaction for 5 hours, the catalyst was removed by filtration of the reactant, the solvent n-pentane was distilled off, a white solid was precipitated by cooling, and recrystallized with ethanol to obtain 38 g of tetrahydrocyclopentadiene tetramer.

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PUM

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Abstract

The invention provides a synthetic method of tetrahydrotetracyclopentadiene. Cyclopentadiene is used as a starting material; a reaction solvent is added; and reactive synthesis is carried out through two steps of Diels-Alder addition and catalytic hydrogenation reduction. The product is tetrahydrotetracyclopentadiene. The synthetic method comprises the following processes: cyclopentadiene and the reaction solvent are mixed and added into a high pressure reactor, nitrogen is filled, and a reaction is carried out at 170-230 DEG C for 8-24h; a hydrogenation catalyst is added into the above reaction system, wherein hydrogen pressure is 1MPa-4MPa, reaction temperature is 110-170 DEG C and reaction time is 5-15h. The invention has the following advantages: the synthetic method is simple, and the Diels-Alder reaction and the hydrogenation reduction reaction can be carried out in the same reaction system; the raw material cyclopentadiene is a cheap industrial by-product of ethene and has a wide source; and yield is high.

Description

technical field [0001] The invention relates to a novel high-density hydrocarbon fuel and a synthesis method thereof, belonging to the high-density hydrocarbon fuel preparation technology. Background technique [0002] With the development of modern aerospace technology, a series of flight performances such as range, speed, and payload of various aircraft have been greatly improved, which requires the fuel used to have better propulsion capabilities. High-density hydrocarbon fuels have greater mass density and volumetric calorific value than ordinary hydrocarbon fuels. With a certain volume of the engine fuel tank, the greater the fuel density, the more fuel can be carried, which effectively increases the Energy, which meets the requirements of high speed, large load and long range of the aircraft; or under the condition of keeping the performance of the aircraft unchanged, the use of high-density hydrocarbon fuel can reduce the volume of the fuel tank, make the aircraft min...

Claims

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Application Information

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IPC IPC(8): C07C13/64C07C5/03
Inventor 邱贤平韦伟陈克海鲁统洁金凤
Owner HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY