2-adamantanecarboxylic acid and 1-adamantane methanol separation and purification method

A technology of adamantane carboxylic acid and adamantane methanol, applied in the separation/purification of carboxylic acid compounds, separation/purification of hydroxyl compounds, chemical instruments and methods, etc., can solve the problems of difficult separation of mixtures, difficult separation, and environmental pollution. Achieve the effects of improving product purity, thorough esterification, and convenient operation

Inactive Publication Date: 2016-02-03
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because the two have similar molecular weight, functional groups and parent rings, the properties between the two are close, and the separation of the mixture is difficult, especially the separation of the mixture (recrystallization residue, etc.) with close content is more difficult and pollutes the environment.
And there is no disclosure in the prior art that 2-adamantanecarboxylic acid and 1-adamantanemethanol are separated by liquid phase extraction

Method used

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  • 2-adamantanecarboxylic acid and 1-adamantane methanol separation and purification method
  • 2-adamantanecarboxylic acid and 1-adamantane methanol separation and purification method
  • 2-adamantanecarboxylic acid and 1-adamantane methanol separation and purification method

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Experimental program
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Effect test

Embodiment 1

[0030] Such as figure 1 As shown, add 10 grams of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid mixture raw materials (mass ratio 1:1) into a 100mL round bottom flask, add 30mL of methanol, add 3 grams of mass fraction 98% sulfuric acid as a catalyst, Raise the temperature to 65°C and carry out the esterification reaction with magnetic stirring. After reacting for 30 minutes, the reaction system was sampled, 1 mL of water was added, extracted with 1 mL of ethyl acetate and injected into GC for analysis. GC analysis results such as figure 2 Shown, wherein tR6.950 is 1-adamantane carboxylate, tR7.183 is 2-adamantane carboxylate. Stop the reaction for separation, add 60 mL of ice water, and separate the liquids. 10.8 g of the separated mixed methyl adamantane carboxylate was added, 22 mL of isopropanol was added, the water bath was refluxed for reaction, and 1.6 g of sodium borohydride and 1.8 g of anhydrous lithium chloride were added in batches to reduce the r...

Embodiment 2

[0032]In the 100mL round bottom flask that 10 grams of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid mixture raw material (1-adamantanecarboxylic acid about 95%, 2-adamantanecarboxylic acid about 5%) were added, 30mL of methanol was added, and 4 Sulfuric acid with a gram mass fraction of 98% was used as a catalyst, and the temperature was raised to 55°C with magnetic stirring to carry out the esterification reaction. After reacting for 60 minutes, stop the esterification reaction for separation, add 60 mL of ice water, and separate by liquid separation. Add 55 mL of isopropanol to the separated methyl adamantane carboxylate, reflux in a water bath, add 2.6 g of sodium borohydride and 2.9 g of anhydrous lithium chloride in batches, and reduce the reaction for about 30 minutes to complete. Add 100 mL of ice water, separate the layers, add 2 mL of 10% NaOH solution to the organic layer, reflux for hydrolysis for 30 min, and saponify completely. Add 50 mL of ice wat...

Embodiment 3

[0034] Add 10g of 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid mixture raw material (about 25% of 1-adamantanecarboxylic acid, about 75% of 2-adamantanecarboxylic acid) into a 100mL round bottom flask, add 20mL of methanol, add 2 grams of mass Sulfuric acid with a fraction of 98% was used as a catalyst, and the temperature was raised to 70° C. in a water bath, refluxed, and magnetically stirred to carry out esterification. After reacting for 30 minutes, stop the esterification reaction for separation, add 40 mL of ice water, and separate by liquid separation. Add 55 mL of isopropanol to the isolated mixed methyl adamantane carboxylate, reflux in a water bath, add 1.4 g of sodium borohydride and 1.5 g of anhydrous lithium chloride in batches, and reduce the reaction for about 30 minutes to complete. Add 100 mL of ice water, separate the layers, and add 30 mL of 10% NaOH solution to the organic layer for reflux hydrolysis for 60 minutes to complete saponification....

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Abstract

The present invention discloses a 2-adamantanecarboxylic acid and 1-adamantane methanol separation and purification method comprising the following steps: 1-adamantanecarboxylic acid and 2-adamantanecarboxylic acid are dissolved in methanol to obtain a liquid mixture A, esterification of the liquid mixture A is first performed to obtain a liquid mixture B, sulfuric acid with the mass fraction of not less than 98% is used as a catalyst of the esterification reaction, the mass ratio of the catalyst and the mixed adamantanecarboxylic acid is 2 to 4:10, the reaction time is 30-60min, and the reaction temperature is 55 to 70 DEG C; reduction reaction of the obtained liquid mixture B is performed to obtain a liquid mixture C, sodium borohydride and lithium chloride are used as reducing agents, the reaction time is 30-120min, and the reaction temperature is 70-85 DEG C; the resulting liquid mixture C is added into a NaOH solution for saponification reaction, an aqueous layer B and an organic layer C are obtained by separation; the separated organic layer C is further purified to obtain 1-adamantane methanol; the separated aqueous layer B is further acidified to obtain 2-adamantanecarboxylic acid. The method is simple and easy to control, and two high-purity 1-adamantane methanol and 2-adamantanecarboxylic acid can be obtained simultaneously.

Description

technical field [0001] The invention relates to a method for separating and purifying an adamantanecarboxylic acid mixture, in particular to a method for separating and purifying 2-adamantanecarboxylic acid and 1-adamantanemethanol. Background technique [0002] Adamantane is a positively symmetrical and very stable cage-like hydrocarbon, which is widely used in medicine, functional polymers, surfactants, lubricants, photographic photosensitive materials, aviation and so on. Adamantane is a cyclic tetrahedral hydrocarbon containing 10 carbon atoms and 16 hydrogen atoms. Its basic structure is chair-shaped cyclohexane, which is a highly symmetrical and very stable compound. Adamantane has the following characteristics: very stable to light, good lubricity, extremely lipophilic, basically odorless, and is a sublimate. Although the reactivity is not as good as that of benzene, it is very easy to synthesize its derivatives. Due to its compact structure and good fat solubility, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C61/135C07C35/37C07C29/147C07C29/76C07C51/42C07C27/02C07C51/02
CPCC07C29/147C07C29/76C07C51/02C07C51/09C07C51/42C07C61/135C07C35/37
Inventor 胡晓春孔黎春李士坤
Owner ZHEJIANG NORMAL UNIVERSITY
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