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A kind of preparation method of 1,3 adamantane dicarboxylic acid

A technology of dicarboxylic acid and adamantane is applied in the preparation of carboxylate, the preparation of organic compounds, chemical instruments and methods, etc. It can solve the problems of many equipment and solvents, long synthesis routes, large acid consumption, etc., and achieve the reaction steps. The effect of short, less reagent and high conversion rate

Active Publication Date: 2017-05-10
ZHEJIANG HUAJI BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Among the above several preparation methods, method 1 adopts adamantane as a starting raw material, and the synthetic route is relatively long, and involves the recovery and utilization of silver salt and bromine in the process, the operation is complicated, and more equipment and solvents are needed; method 2 The use of precious metal salt silver sulfate is avoided, and the consumption of bromine is also reduced, but the route is still long and the operation is complicated; Method 3 adopts adamantanecarboxylic acid as the starting material, and the reaction steps are greatly simplified, but still need two steps to complete, the first step The reaction product needs to be separated and purified before proceeding to the second step reaction, which consumes a lot of acid

Method used

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  • A kind of preparation method of 1,3 adamantane dicarboxylic acid
  • A kind of preparation method of 1,3 adamantane dicarboxylic acid
  • A kind of preparation method of 1,3 adamantane dicarboxylic acid

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Effect test

Embodiment 1

[0024] Add 100mL of concentrated sulfuric acid to a 250mL four-neck flask equipped with a mechanical stirrer, reflux condenser, constant pressure dropping funnel, and thermometer, and slowly add 1-adamantanylmethyl ketone (R=CH 3 ) 15g (84.1mmol), keep it for 15 minutes after the addition, control 0°C in an ice-water bath, and then slowly add the mixed acid solution (fuming nitric acid 16ml (0.34mol) + concentrated sulfuric acid 16ml) within 30 minutes with a constant pressure dropping funnel , after the addition, keep it warm for 1 hour, naturally raise the temperature to 20°C and react for 10 hours. After the reaction is over, slowly pour the reaction liquid into 200 mL of ice water and stir while pouring. A white solid precipitates out. The filter cake is washed with a small amount of water and vacuum After drying, 11.4 g of white powder solid was obtained, with a content of 98%, and a yield of 60.5%.

Embodiment 2

[0026] Add 100mL of concentrated sulfuric acid to a 250mL four-neck flask equipped with a mechanical stirrer, reflux condenser, constant pressure dropping funnel, and thermometer, and slowly add 1-adamantanylmethyl ketone (R=CH 3 ) 15g (84.1mmol), keep it for 15 minutes after the addition, control 0°C in an ice-water bath, and then slowly add the mixed acid solution (fuming nitric acid 8ml (0.17mol) + concentrated sulfuric acid 40ml) within 30 minutes with a constant pressure dropping funnel , after the addition, keep it warm for 1 hour, naturally heat up to 40°C and react for 5 hours. After the reaction is over, slowly pour the reaction solution into 200 mL of ice water and stir while pouring. A white solid precipitates out, and the precipitate is obtained by suction filtration. Wash the filter cake with a small amount of water and vacuum After drying, 9.7 g of white powder solid was obtained, with a content of 90% and a yield of 51.5%.

Embodiment 3

[0028] Add 100mL of concentrated sulfuric acid to a 250mL four-neck flask equipped with a mechanical stirrer, reflux condenser, constant pressure dropping funnel, and thermometer, and slowly add 1-adamantanylmethyl ketone (R=CH 3 ) 15g (84.1mmol), keep it for 15 minutes after the addition, control 0°C in an ice-water bath, and then slowly add the mixed acid solution (fuming nitric acid 16ml (0.34mol) + concentrated sulfuric acid 32ml) within 30 minutes with a constant pressure dropping funnel , after the addition, keep it warm for 1 hour, naturally heat up to 60°C and react for 8 hours. After the reaction is over, slowly pour the reaction solution into 200 mL of ice water and stir while pouring. A white solid precipitates out. The filter cake is washed with a small amount of water and vacuum After drying, 14.8 g of white powder solid was obtained, with a content of 98%, and a yield of 78.6%.

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Abstract

The invention belongs to the technical field of organic synthesis and relates to a preparation method of adamantane disubstituted derivates, in particular to a preparation method of 1,3-adamantanedicarboxylic acid. 1,3-adamantanedicarboxylic acid is directly prepared with a one-step method, and raw materials directly generate 1,3-adamantanedicarboxylic acid in a mixed acid solution of concentrated sulfuric acid and fuming nitric acid. The preparation method has the advantages that the raw materials are novel, a one-pot reaction step is short, a few reagents are used, the economic efficiency of the raw materials is good, the operation is simple and convenient, and the conversion rate is higher.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a preparation method of disubstituted adamantane derivatives, in particular to a preparation method of 1,3-adamantane dicarboxylic acid. Background technique [0002] 1,3-Adamantane dicarboxylic acid is an intermediate commonly used by many promising adamantane disubstituted derivatives because of its dual functional groups. Novakom reported that adamantane dicarboxylic acid derivatives were catalyzed hydrogenated to obtain adamantane diamine substituted derivatives, which have good antiviral effects, especially anti-influenza viruses; Japan Synthetic Rubber Co.Ltd reported that 1,3- Adamantane dicarboxylic acid, esterified with propylene alcohol under acid catalysis, and finally polymerized to prepare polymer materials, has the characteristics of good transparency, high hardness, excellent impact resistance and thermal stability, and has a wide range of applications in t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C61/135C07C51/305
CPCC07C51/305C07C61/135
Inventor 高鋆李宝强蒋晓青贾中辉朱启东
Owner ZHEJIANG HUAJI BIOTECH