Tetracyclic decene dimer synthesis method

A tetracyclodedecane dimer and synthesis method technology, applied in the direction of chemical instruments and methods, hydrocarbons, hydrocarbons, etc., can solve the problem of serious injury to operators, high toxicity of chemical reagents, tetracyclodedecane The problem of high cost of dimer synthesis achieves the effect of increasing yield

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

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Problems solved by technology

[0014] 2. The chemical reagents used are highly toxic and harmful to operators, such as tetracyclodecane azide, CH 2 Cl 2 Solvent, etc.
[0015] 3. The synthesis cost of tetracyclodecane dimer is relatively high, and the cost of reagents and solvents used are relatively high, such as n-BuSnCl, (p-Br-C 6 h 4 )4N (1+) Sb 6 (1-) Wait

Method used

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  • Tetracyclic decene dimer synthesis method
  • Tetracyclic decene dimer synthesis method
  • Tetracyclic decene dimer synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Add 100 ml of anhydrous tetrahydrofuran into a 500 ml three-necked flask, protect it with argon, and keep the temperature at 0°C. Add 11.38 g (0.060 mol) of titanium tetrachloride dropwise within 30 minutes with a horizontal pressure funnel, and stir rapidly; then batch A total of LiAlH was added 4 5.31 g (0.140 mol) g, after the dropwise addition, remove the cooling device, stir at room temperature for 30 minutes, then heat to 60-70°C and reflux for 30 minutes. After reflux, cool down to 0°C again, add 4.80 g (0.0607 mol) of pyridine dropwise; then add 120 ml of tetrahydrofuran solution of 10.00 g (0.0667 mol) tetracyclodecanone dropwise, remove the cooling device, and heat to 60-70 ℃, reflux reaction for 24 hours (argon protection). After the reaction, cool to room temperature, add 300 ml of newly prepared 10% potassium carbonate solution dropwise, filter, wash the filter cake twice with anhydrous ether, then combine the filtrates, wash with distilled water (3×50 ml...

Embodiment 2

[0029] Add 100 ml of anhydrous tetrahydrofuran to a 500 ml three-neck flask, protect it with argon, and keep the temperature at 0°C. Add 13.77 g (0.0726 mol) of titanium tetrachloride dropwise within 30 minutes with a horizontal pressure funnel, and stir rapidly; then batch A total of LiAlH was added 4 5.81 g (0.153 mol), after the dropwise addition, remove the cooling device, stir at room temperature for 30 minutes, then heat to 60-70°C and reflux for 30 minutes. After reflux, cool down to 0°C again, add 4.89 g (0.0618 mol) of pyridine dropwise; then add 120 ml of tetrahydrofuran solution of 10.00 g (0.0667 mol) tetracyclodecanone dropwise, remove the cooling device, and heat to 60-70 °C, reflux for 24 hours (argon protection). After the reaction, cool to room temperature, add 300 ml of newly prepared 10% potassium carbonate solution dropwise, filter, wash the filter cake twice with anhydrous ether, then combine the filtrates, wash with distilled water (3×50 ml), and use th...

Embodiment 3

[0031]Add 100 ml of anhydrous tetrahydrofuran into a 500 ml three-neck flask, protect it with argon, and keep the temperature at 0°C. Add 16.45 g (0.0867 mol) of titanium tetrachloride dropwise within 30 minutes with a horizontal pressure funnel, and stir rapidly; then batch A total of 6.34 g (0.167 mol) of LiAlH4 was added each time. After the dropwise addition, the cooling device was removed, stirred at room temperature for 30 minutes, and then heated to 60-70°C for 30 minutes under reflux. After reflux, cool down to 0°C again, add 5.01 g (0.0634 mol) of pyridine dropwise; then add 120 ml of tetrahydrofuran solution of 10.00 g (0.0667 mol) tetracyclodecanone dropwise, remove the cooling device, and heat to 60-70 °C, reflux for 24 hours (argon protection). After the reaction, cool to room temperature, add 300 ml of newly prepared 10% potassium carbonate solution dropwise, filter, wash the filter cake twice with anhydrous ether, then combine the filtrates, wash with distilled ...

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Abstract

The invention provides a tetracyclic decene dimer synthesis method. A tetracyclic decylone is used as an initial raw material and undergoes a carbonyl reduction coupling reaction to synthesize a tension ring cage hydrocarbon tetracyclic decene dimer (C20H28). Compared with the prior art, the synthesis method has the advantages of simple synthetic technology, low cost, high synthetic yield and high product purity, and allows the target compound to be synthesized only through a one-step reaction, the yield to reach about 87% and the purity of the product to reach above 98%; and the tetracyclic decene dimer can be used as the fuel or fuel additive of solid rocket engines.

Description

technical field [0001] The invention relates to a method for synthesizing tensioned ring cage hydrocarbons - tetracyclodedecane dimers (also known as adamantane dimers). The hydrocarbons synthesized by this method have high yield and high purity. High, and the reaction method is simple and low cost. The compound can be used as high-density hydrocarbon fuel or high-energy additive in rocket engines. Background technique [0002] Due to the ring tension energy in the compound molecule, the strained ring cage hydrocarbon increases the calorific value of combustion. When endothermic cracking, once a certain bond is broken, the whole molecule will be broken quickly, releasing energy, and reducing the occurrence of carbon deposition, which has obvious performance advantages. The high-density strained ring cage hydrocarbon is a special type of high-energy-density material (HEDM). All or most of their molecules are composed of carbon and hydrogen, and they have positive heat of fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/207C07C13/61
Inventor 鲁统洁蔡克龙陈克海韦伟叶丹阳邱贤平金凤
Owner HUBEI INST OF AEROSPACE CHEMOTECHNOLOGY
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