Method for catalytically synthesizing adamantane

A technology of adamantane and main catalyst, applied in the direction of organic chemistry, isomerization hydrocarbon production, etc., can solve the problems of low yield and increased cost, and achieve the effect of cheap and easy-to-obtain raw materials, easy control, and simple and easy experimental methods

Inactive Publication Date: 2009-04-15
ANHUI UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Japan's Idemitsu Kosan Co., Ltd. tried to use molecular sieves as the skeleton and add Ni, Co, Pt, Re, Fe, Cu and other metals as isomerization catalysts. Although the use of this catalyst can avoid the pollution and three wastes when using halide catalysts, But pressurization is required, the yield is very low and the cost increases

Method used

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  • Method for catalytically synthesizing adamantane

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Embodiment 1

[0019] A method for catalytically synthesizing adamantane, the steps are:

[0020] A. Isomerization into pendant tetrahydrodicyclopentadiene (exo-TCD): add bridged tetrahydrodicyclopentadiene 13.6g, anhydrous aluminum trichloride (main catalyst) 2.0g in a 250ml three-necked flask, dry (Anhydrous CaCl 2 ) over 2.4ml of 1,2-dichloroethane, start stirring to dissolve bridged tetrahydrodicyclopentadiene slowly, the reaction temperature is 20°C or 25°C, the reaction time is 30min, and the reaction product is directly used in the next step reaction;

[0021] B, the synthesis of adamantane (ADH): after the above reaction is completed, add 3.0g anhydrous aluminum trichloride and 0.20g water, the reaction temperature is 60°C or 70°C, and the reaction time is 3 hours. Add 30ml petroleum ether into the flask, stir, and after the adamantane is completely dissolved, let stand for 10min. Pour the supernatant into a 100ml beaker, place it in an ice-water bath to cool, and keep the tempera...

Embodiment 2

[0023] In a 250ml three-necked flask, add bridged tetrahydrodicyclopentadiene 16g, anhydrous aluminum trichloride 2.5g, dry (anhydrous CaCl 2 ) over 3.6ml of 1,2-dichloroethane, start stirring to slowly dissolve the bridged tetrahydrodicyclopentadiene, the reaction temperature is 30°C or 35°C, the reaction time is 40min, then add 3.0g of anhydrous trichloro Aluminum and 0.30g sodium bicarbonate, the reaction temperature is 60°C or 65°C, and the reaction time is 3.5 hours. After the reaction, add 40ml of n-hexane into the three-necked flask, stir, and let the adamantane dissolve completely for 10 minutes. Pour the supernatant into a 100ml flask, and evaporate until the adamantane is completely crystallized. After the adamantane is air-dried at room temperature for 4 hours, a white crystalline adamantane with a purity of 99% and a melting point of 269°C (sealed tube) can be obtained. 10g, the yield of adamantane is 62.5%.

Embodiment 3

[0025] In a 250ml three-necked flask, add 20g of bridged tetrahydrodicyclopentadiene, 4.0g of anhydrous aluminum trichloride, and 4.0ml of dried 1,2-dichloroethane, and start stirring to make bridged tetrahydrodicyclopentadiene The diene dissolves slowly, the reaction temperature is 40°C or 50°C, the reaction time is 1 hour, then add 4.0g of anhydrous aluminum trichloride and 0.40g of sodium carbonate, the reaction temperature is 80°C or 90°C, the reaction time is 4 hours, and the reaction ends After that, the temperature was lowered to 40°C, 10ml of n-hexane was added into the three-necked flask, stirred, and after the adamantane was completely dissolved, it was left to stand for 10 minutes, and the extraction was repeated 3 times. The supernatant was poured into a 100ml flask, and evaporated until the adamantane was completely crystallized. After the adamantane was air-dried at room temperature for 6 hours, 13.5 g of white crystal adamantane with a purity of 99.5% was obtaine...

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Abstract

The invention discloses a method for catalyzing and synthesizing adamantane which is generated by bridge tetrahydro Dicyclopentadiene in two steps of catalytic isomerization; adamantane is generated by bridge tetrahydro Dicyclopentadiene as raw material and any of aluminium choride, aluminium tribromide, or ferric trichloride as a catalyst under a normal pressure, a certain temperature, and a certain reaction time. The method is characterized in that the reaction is accomplished in two steps; in the first step, any of methanol, ethanol, normal propyl alcohol, isopropanol, methyl ethyl ketone, acetone, acetic acid, halogenated hydrocarbon, and tetrahydrofuran is used as solvent; in the second step, a certain amount of main catalyst is added, and any of sodium carbonate, sodium chloride or sodium bicarbonate is added as a cocatalyst, thus generating the adamantane under a certain reaction temperature. The method is simple and convenient; the operation is convenient; the yield coefficient is high; and the cost is low. Through a suitably chosen catalyst system, the purity of the adamantane obtained with the method is higher than 99 percent; and the yield coefficient is higher than 60 percent.

Description

technical field [0001] The invention relates to the technical field of adamantane synthesis, and more specifically relates to a method for synthesizing adamantane through two-step isomerization of bridged tetrahydrodicyclopentadiene. As an important fine chemical product, adamantane is widely used in the fields of medicine, polymer materials, lubricants, catalysts, photographic photosensitive materials and aviation. As the raw material of amantadine, a new type of anti-cold drug, adamantane has been recognized by the market. Researching and improving the synthetic method of adamantane has important application value. Background technique [0002] The introduction of the adamantane skeleton into the main chain or side chain of polyester, polyurethane, polyether, polysulfone, polyethylene, epoxy resin and other polymers can improve its performance, thereby making compounds with excellent optical properties, which can be used as organic Glass coatings, optical fibers, photose...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/615C07C5/31
Inventor 李广学刘银王亚男王震张茂润
Owner ANHUI UNIV OF SCI & TECH
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