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Methyl pentacyclic undecanedione synthesis method

A technology for the synthesis of methylpentacycloundecanedione and its synthesis method, which is applied in the field of synthesis of methylpentacycloundecanedione, can solve the problems affecting the synthesis and application of MPCU compounds, complicated synthesis process and high cost, Achieve the effects of shortening the synthesis cycle, high yield and low cost

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

AI Technical Summary

Problems solved by technology

[0012] Although they made some improvements to Marchand's synthesis method, the synthesis process of this method is still relatively complicated, resulting in low yield and high cost, which affects the synthesis and application of MPCU compounds

Method used

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  • Methyl pentacyclic undecanedione synthesis method
  • Methyl pentacyclic undecanedione synthesis method
  • Methyl pentacyclic undecanedione synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 108.0 g (1.0 mol) of p-benzoquinone to a 2000 ml three-necked flask, and add 1000 ml of methanol solvent. After the methanol solution of p-quinone was cooled to -40°C, 800.0 g (10.0 mol) of methylcyclopentadiene was added dropwise to the solution, the dropping rate was controlled at one drop per second, and stirring was started. After the dropwise addition, slowly return to room temperature. The reaction liquid after the addition was poured into a quartz glass test tube, and irradiated with ultraviolet light for 10 hours. After extraction and purification, 159.81 g of the product was obtained with a yield of 85%.

Embodiment 2

[0033] Add 54.0 g (0.5 mol) of p-benzoquinone to a 500 ml three-necked flask, and add 300 ml of ethanol solvent. After the ethanol solution of p-quinone was cooled to 20°C, 40.0 g (0.5 mol) of methylcyclopentadiene was added dropwise to the solution, the dropping rate was controlled at one drop per second, and stirring was started. After the dropwise addition was completed, it was slowly raised to room temperature. The reaction liquid after addition was poured into a quartz glass test tube, and irradiated with ultraviolet light for 40 hours. After extraction and purification, 85.5 g of the product was obtained with a yield of 91%.

Embodiment 3

[0035]Add 810.0 g (7.5 mol) of p-benzoquinone to a 2000 ml three-necked flask, and add 1000 ml of propylene glycol solvent. After cooling the propylene glycol solution of p-quinone to 0°C, add 60.0 g (0.75 mol) of methylcyclopentadiene dropwise to the solution at a rate of one drop per second and start stirring. After the dropwise addition was completed, it was slowly raised to room temperature. The reaction liquid after addition was poured into a quartz glass test tube, and irradiated with ultraviolet light for 30 hours. After extraction and purification, 129.7 g of the product was obtained with a yield of 92%.

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Abstract

A methyl pentacyclic [5.4.0.0<2,6>.0<3,10>.0<5,9>] undecanedione synthesis method allows methyl pentacyclic [5.4.0.0<2,6>.0<3,10>.0<5,9>] undecanedione to be synthesized through a Diels-Alder addition and ultraviolet cyclization two-step continuous reaction of raw materials comprising methyl cyclopentadiene and p-benzoquinone in an alcohol solvent. Compared with traditional methods, the synthesis method which only uses one solvent in the two-step reaction has the advantages of solvent kind reduction, raw material cost reduction, omitting of a post-treatment process of the addition reaction, reduction of technologies comprising distillation, purification, drying and the like of an addition product, synthetic efficiency improvement, synthetic period shortening, and synthetic cost reduction, and improves the total yield to about 90% from 70.6% by combining a two-step reaction to form a continuous reaction.

Description

technical field [0001] The invention relates to a high-density hydrocarbon fuel synthesis intermediate-methyl pentacyclo[5.4.0.0 2,6 .0 3,10 .0 5,9 ] Undecanedione (molecular formula is C 12 h 12 o 2 ), the intermediate is a synthetic methyl pentacyclic [5.4.0.0 2,6 .0 3,10 .0 5,9 ] Undecane (hereinafter referred to as MPCU) and its olefin dimer are key raw materials for high-density hydrocarbons, MPCU and its olefin dimer can be used as high-density fuels or additives for aircraft such as (high) supersonic missiles . Background technique [0002] High-energy-density hydrocarbon fuel is one of the keys to the research and development of ramjet rocket engines. The use of high-density energetic tension ring-cage hydrocarbon propellants can enable ramjet engines to achieve solidification of missile propulsion systems, high specific impulse, and hypersonic speed. and low characteristic signal, and endow the propellant with excellent ignition and combustion performance, ...

Claims

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Application Information

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IPC IPC(8): C07C49/423C07C45/61
Inventor 叶丹阳陈克海韦伟鲁统洁邱贤平金凤
Owner HUBEI INST OF AEROSPACE CHEMOTECH
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