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Synthesis of cyclopentadiene or substituted cyclopentadiene

A technology of cyclopentadiene and cyclopentene, which is applied in the production of hydrocarbons from oxygen-containing organic compounds, organic chemistry, etc., can solve the problems that cannot reflect the actual yield of the target product, and the separation of the reaction mixture is difficult.

Inactive Publication Date: 2005-09-28
PETROCHINA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcoming of this method is: contain a large amount of trisubstituted cyclopentadiene (accounting for 35% of total product) in the reaction mixture, the separation of reaction mixture is more difficult
Therefore, it cannot reflect the actual yield of the target product in the whole process

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] After the reaction flask has been fully inertly replaced, add 1 g of a mixture consisting of ferric chloride (0.3 g) and copper chloride (0.7 g), 250 ml of diethyl ether and 17 g of lithium aluminum hydride, start stirring, and cool the mixture to 0 °C, under constant stirring, slowly drop 40 g (0.29 mol) of 2,3,4,5-tetramethylcyclopent-2-en-1-one into the reaction flask. After the addition, continue to stir for 0.5 hours, slowly raise the temperature to 25° C. and stir for 3 hours, and slowly add acidic distilled water with pH=2 until the hydrolysis is complete. Add 200ml of benzene and 62.8g of p-toluenesulfonic acid, and reflux for 12 hours in a boiling state to stop the reaction. The liquid in the reaction mixture was separated by decantation, the remaining solid was washed twice with ether and the washing liquid was mixed with the liquid obtained by decantation, neutralized to neutral with saturated sodium carbonate solution, the organic layer was washed twice with...

Embodiment 2

[0033] After the reaction flask has been fully inertly replaced, add 1g of a mixture consisting of ferric chloride (0.5g) and copper chloride (0.5g), 250ml of 1 ether and 17g of lithium aluminum tetrahydride in turn, start stirring, and cool the mixture to 0 °C, under continuous stirring, slowly drop 40 g of 2,3,4,5-tetramethylcyclopent-2-en-1-one into the reaction flask. After the addition, continue to stir for 0.5 hours, slowly raise the temperature to 25° C. and stir for 3 hours, and slowly add acidic distilled water with pH=2 until the hydrolysis is complete. Add 200ml of benzene and 20.88g of glacial acetic acid, and reflux for 12 hours in a boiling state to stop the reaction. The liquid in the reaction mixture was separated by decantation, the remaining solid was washed twice with ether and the washing liquid was mixed with the liquid obtained by decantation, neutralized to neutral with saturated sodium carbonate solution, the organic layer was washed twice with water, a...

Embodiment 3

[0035] After the reaction bottle has been fully inertly replaced, add 1g of ferric chloride, 250ml of 1 ether and 17g of lithium aluminum tetrahydride in sequence, start stirring, and cool the mixture to 0°C. Under constant stirring, add 40g of 2, 3, 4, 5-Tetramethylcyclopent-2-en-1-one was slowly added dropwise into the reaction flask. After the addition, continue to stir for 0.5 hours, slowly raise the temperature to 25° C. and stir for 3 hours, and slowly add acidic distilled water with pH=2 until the hydrolysis is complete. Add 200ml of benzene and 40.4g of benzoic acid, and reflux for 12 hours in a boiling state to stop the reaction. The liquid in the reaction mixture was separated by decantation, the remaining solid was washed twice with ether and the washing liquid was mixed with the liquid obtained by decantation, neutralized to neutral with saturated sodium carbonate solution, the organic layer was washed twice with water, anhydrous magnesium sulfate Drying, filtrati...

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PUM

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Abstract

The present invention provides the synthesis process of cyclopentadiene or substituted cyclopentadiene, and features that during the catalytic reduction reaction of producing cyclopentadiene or substituted cyclopentadiene with cyclopentenone or substituted cyclopentenone, Lewis acid is used to raise the yield of cyclopentadiene or substituted cyclopentadiene greatly and simplify the technological process.

Description

technical field [0001] The present invention relates to the synthesis method of cyclopentadiene or substituted cyclopentadiene. Background technique [0002] Cyclopentadiene or substituted cyclopentadiene is one of the most important ligands in transition metal chemistry. Cyclopentadiene, tetramethylcyclopentadiene, and pentamethylcyclopentadiene are very useful ligands in the process of preparing single-site catalysts. They can be used to prepare various metallocene compounds. These compounds are in In the presence of methylaluminoxane (MAO), it is an excellent catalyst for the production of polyolefins such as polyethylene and polypropylene. In addition, cyclopentadiene can also be used as a polymerized monomer or comonomer for the preparation of polycyclopentadiene. [0003] Cyclopentadiene or substituted cyclopentadiene is difficult to obtain. A small amount of cyclopentadiene and methylcyclopentadiene can be obtained from naphtha cracking or pyrolysis gasoline C5 fra...

Claims

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Application Information

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IPC IPC(8): C07C1/22C07C13/15
Inventor 韦少义朱博超吴江魏红郝萍
Owner PETROCHINA CO LTD
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