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Synthetic method of pentacycloundecane

A synthetic method and eleven technology, applied in the field of synthesis of high-density clathrate strained ring hydrocarbon - pentacycloundecane (PCUD), which can solve the harsh conditions required for synthesis, limit the use of PCUD, and not suitable for Amplify production and other issues to achieve the effects of reducing synthesis costs, increasing operability and safety, and saving manpower

Active Publication Date: 2013-07-17
HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, whether it is the synthetic route of Philip E. Eaton or Alan P. Marchand, the conditions required for the synthesis are very harsh, and there are many synthetic steps. After each step of reaction, steps such as vacuum distillation, filtration, drying, and dissolution are required. The operation is troublesome, the cost is high, the yield is low, and it is not suitable for scale-up production, thus limiting the use of PCUD as an excellent fuel or fuel additive

Method used

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  • Synthetic method of pentacycloundecane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Tricycloundecanedienedione (C 11 h 8 o 2 )Synthesis:

[0029] Diels-Alder addition reaction of cyclopentadiene and benzoquinone: add benzoquinone (2690g, 24.88mol) and 15L of dipropylene glycol in a 25L jacketed kettle, add cyclopentadiene (1860g, 27.3mol) dropwise, Stir and control the temperature of the solution at 0-5°C. After the dropwise addition, the reaction was carried out for 1 hour, and the temperature of the reaction system was slowly raised to room temperature. After the stirring was stopped, a brownish-yellow solution appeared in the reaction kettle.

[0030] Pentacycloundecanedione (C 11 h 8 o 2 )Synthesis:

[0031] The above solution was put into a quartz glass tube with a diameter of 2.5 cm, and irradiated with ultraviolet light for 25 hours to obtain a dipropylene glycol transparent solution containing pentacycloundecanedione, with a chromatographic yield of 92%.

[0032] Pentacycloundecane (C 11 h 14 , PCUD) synthesis:

[0033] Put the dipro...

Embodiment 2

[0036]Tricycloundecanedienedione (C 11 h 8 o 2 )Synthesis:

[0037] Diels-Alder addition reaction of cyclopentadiene and benzoquinone: add benzoquinone (2690g, 24.88mol) and 15L of diethylene glycol in a 25L jacketed kettle, add cyclopentadiene (1860g, 27.3mol) dropwise , stir, and control the temperature of the solution at 5-10°C. After the dropwise addition, the reaction was carried out for 1 hour, and the temperature of the reaction system was slowly raised to room temperature. After the stirring was stopped, a brownish-yellow solution appeared in the reaction kettle.

[0038] Pentacycloundecanedione (C 11 h 8 o 2 )Synthesis:

[0039] The above solution was put into a quartz glass tube with a diameter of 2.5 cm, and irradiated with ultraviolet light for 22 hours to obtain a diethylene glycol transparent solution containing pentacycloundecanedione, with a chromatographic yield of 90%.

[0040] Pentacycloundecane (C 11 h 14 , PCUD) synthesis:

[0041] Put the dieth...

Embodiment 3

[0043] Tricycloundecanedienedione (C 11 h 8 o 2 )Synthesis:

[0044] Diels-Alder addition reaction of cyclopentadiene and benzoquinone: add benzoquinone (2160g, 20mol) and 12L of dipropylene glycol in a 25L jacketed kettle, add cyclopentadiene (1498g, 22.0mol) dropwise, and stir , the temperature of the solution is controlled at 0-5°C. After the dropwise addition, the reaction was carried out for 1 hour, and the temperature of the reaction system was slowly raised to room temperature. After the stirring was stopped, a brownish-yellow solution appeared in the reaction kettle.

[0045] Pentacycloundecanedione (C 11 h 8 o 2 )Synthesis:

[0046] The above solution was put into a quartz glass tube with a diameter of 2.5 cm, and irradiated with ultraviolet light for 30 hours to obtain a dipropylene glycol transparent solution containing pentacycloundecanedione, with a chromatographic yield of 93%.

[0047] Pentacycloundecane (C 11 h 14 , PCUD) synthesis:

[0048] Put the ...

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Abstract

The invention provides a synthetic method of pentacycloundecane (PCUD). The method uses cyclopentadiene and benzoquinone as initial raw materials, and a high boiling solvent; and the pentacycloundecane is synthesized through the following three reactions: Diels-Alder addition, ultraviolet cyclization and carbonyl reduction. According to the invention, the Diels-Alder addition, the ultraviolet cyclization and the carbonyl reduction can be continuously carried out without post-treatment, and unnecessary processes in the reactions is simplified, thereby achieving purposes of improving efficiency and reducing cost. The method has advantages of short period, low cost and easily expanded technology; and the synthesized target compound PCUD can be used as a high-energy additive for fuel of solid turbine stamping engines or liquid rocket fuel.

Description

technical field [0001] The invention relates to a method for synthesizing a high-density clathrate strained ring hydrocarbon—pentacycloundecane (PCUD), which can be used as a fuel-rich propellant for a solid turboramjet engine or a high-energy additive for a liquid rocket fuel. Background technique [0002] At present, the application goals of solid turbo ramjet engines at home and abroad require the use of a fuel-rich propellant with excellent ignition performance, stable combustion, and high calorific value. The research and development of solid high-energy-density hydrocarbon fuel is one of the key raw materials for this fuel-rich propellant, because the advantage of using a fuel-rich propellant containing solid high-density clathrate hydrocarbons is that the ramjet engine can be used as a missile propulsion system The miniaturization, high specific impulse, hypersonic speed and low characteristic signal, and the ignition and combustion performance of the propellant are e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/64C07C1/207
Inventor 陈克海韦伟叶丹阳鲁统洁邱贤平金凤
Owner HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY
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