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Cage hydrocarbon with spiral ring structure as well as preparation method and application of cage hydrocarbon

A spiro-ring structure, cage-like technology, applied in the field of cage-like hydrocarbons and their preparation, can solve the problems of limited application and limited fuel solubility, and achieve the effects of large mass density and volume calorific value, increasing added value and increasing energy.

Pending Publication Date: 2022-05-13
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, PCU itself is highly volatile and has limited solubility in fuels, two disadvantages that limit its application

Method used

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  • Cage hydrocarbon with spiral ring structure as well as preparation method and application of cage hydrocarbon
  • Cage hydrocarbon with spiral ring structure as well as preparation method and application of cage hydrocarbon
  • Cage hydrocarbon with spiral ring structure as well as preparation method and application of cage hydrocarbon

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of cyclopentadiene:

[0063] Depolymerization reaction of dicyclopentadiene: Add 100ml of dicyclopentadiene liquid into a 250ml single-necked round-bottom flask, set up a rectification device, heat the reaction device to 180°C with a heating mantle, and heat to reflux for 25 minutes, when the distillation head When the thermometer at the branch end showed a reading of 42°C, distillate flowed out from the tail joint at this time, and the distillate was a colorless liquid with a gasoline smell, which was monocyclopentadiene. In order to avoid the re-polymerization of the obtained cyclopentadiene monomer at room temperature, the receiving device should be protected at low temperature with an ice-salt bath. When the depolymerization time reaches 1 hour, no distillate flows out from the tail joint, and a total of 70ml of cyclopentadiene monomer is depolymerized, and the depolymerization rate is 70%. The newly prepared cyclopentadiene monomer can be frozen Save f...

Embodiment 2

[0065] Synthetic method 1 of spirocyclization cyclopentadiene:

[0066] A 50% aqueous NaOH solution (1.2 L, 10 equiv), 2,6-di-tert-butyl-p-cresol (20 mg) and methyltributylammonium chloride (75% aqueous solution, 5.35 g , 0.007 equivalent). Then freshly prepared cyclopentadiene (150 g, 2.27 mol, 1 equiv) was added to the above solution at 26 °C. The mixture was stirred at 26°C, and 1,2-dichloroethane (225 g, 1 equivalent) was slowly added dropwise to the above mixture (over 75 min). After the dropwise addition was completed, the stirring reaction was continued at 26° C. for 1 h. After the reaction was completed, the product spiro three-membered cyclocyclopentadiene was distilled off under reduced pressure. Finally, 170 g of product were obtained with a yield of 81%.

[0067] The synthesis of spiro four-membered cyclocyclopentadiene and spiro five-membered cyclopentadiene only needs to replace the raw material 1,2-dichloroethane with 1,3-dichloropropane and 1,4-dichlorobuta...

Embodiment 3

[0069] Synthetic method 2 of spirocyclic cyclopentadiene:

[0070] 120 ml of tetrahydrofuran was added into a double-necked round bottom flask at 0°C as a reaction solvent, and then sodium hydride (18.18 g, 0.45 mol, 2.6 equivalents) was added to the above solvent. Freshly prepared cyclopentadiene (17.42 ml, 0.21 mol, 1 equiv) was slowly added dropwise to the above solution (over 1 h) at 0°C. After the dropwise addition was completed, it was raised to room temperature and continued to stir for 20 minutes, the solution turned pink, then cooled to 0°C, and then 1,2-dichloroethane (13.78ml, 0.17mol, 1 equivalent) was slowly added dropwise To the above mixture (more than 60min). After the dropwise addition was completed, the mixture was raised to room temperature and continued to stir for 12 h. After the reaction, under the condition of 0°C, water-containing tetrahydrofuran was slowly added to the reaction solution to remove excess unreacted sodium hydride. Then add 80ml of wat...

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Abstract

The invention discloses a polyhedral oligomeric hydrocarbon with a spiro structure, which has the following structure: n = 1 or 2 or 3. The invention also discloses a preparation method of the polyhedral oligomeric hydrocarbon with the spiro structure. Compared with traditional high-density fuel JP-10, the spiral cage-shaped hydrocarbon fuel molecule has the advantages that the density is increased by 11.0%, the volume calorific value is increased by 8.3%, and the spiral cage-shaped hydrocarbon fuel molecule has great advantages and can be used as fuel of aircrafts. And under the condition that the same high-density fuel effect is achieved, more fuel is saved, the cost is greatly saved, and the application prospect is good.

Description

technical field [0001] The invention relates to the field of hydrocarbon synthesis, in particular to a cage-like hydrocarbon and its preparation method and application. Background technique [0002] High-density hydrocarbons have high density and high volumetric calorific value of combustion, and are a new type of synthetic fuel, mainly used in propellants for aerospace vehicles. High-density hydrocarbon fuels can be mainly divided into two categories: high-density polycyclic hydrocarbon fuels and high-density cage hydrocarbon fuels. At present, high-density polycyclic hydrocarbon fuel is the main component of aerospace vehicle fuel, and most of them are liquid fuels, and there are many studies on their performance; while high-density cage hydrocarbon fuels are mostly solid, still in the stage of synthesis research, and are mainly used as High-energy additives can improve the volumetric combustion calorific value and other properties of fuels by compounding with other fuels...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/72C07C1/22C10L1/04C06D5/00
CPCC07C13/72C06D5/00C10L1/04C07C2603/94C10L2270/02C10L2270/04
Inventor 朱忠朋赵杰伏朝林陶志平李涛闫瑞贾丹丹
Owner CHINA PETROLEUM & CHEM CORP
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