Preparation method of 2-methyl-2-adamantyl acrylate

A technology of adamantanol acrylate and adamantanone is applied in the field of preparation of 2-methyl-2-adamantanol acrylate and can solve the problems of high corrosiveness, strict production requirements, difficulty in storage and production, etc.

Active Publication Date: 2015-05-20
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, as far as the nature of this type of compound itself is concerned, there are problems of high corrosiveness and strict production requirements
Therefore, there are storage and production difficulties using this type of raw material

Method used

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  • Preparation method of 2-methyl-2-adamantyl acrylate
  • Preparation method of 2-methyl-2-adamantyl acrylate
  • Preparation method of 2-methyl-2-adamantyl acrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053]Step 1. Dissolve 120g of adamantanone in 272ml of anhydrous tetrahydrofuran, and add 192g of 59.37% (wt / wt) methyl bromide in tetrahydrofuran under stirring (methane bromide is passed into tetrahydrofuran at -5°C--0°C), Dissolved and then used.

[0054] Step 2: Add 13g of lithium metal and 300ml of anhydrous tetrahydrofuran (moisture content less than 200ppm) into a 1000ml reaction bottle with mechanical stirring, drop the temperature to -5°C to 0°C while stirring, and start adding the above mixed solution for about 2 hours After finishing, control the temperature at 5°C to 15°C. After dripping, keep it warm for 1 hour, then take a sample and add water to quench the reaction, then TLC (PE:EA=10:1, iodine color development, water soaking), and send the sample to GC after passing the test ( Central control 1), cool down to -10°C ~ -8°C.

[0055] Step 3: Add 2 g of phenothiazine and stir for 10 min.

[0056] Step 4: Start to drop 120g of acrylic anhydride to control the d...

Embodiment 2

[0061] Step 1. Dissolve 150g of adamantanone in 375ml of anhydrous tetrahydrofuran, and add it into the tetrahydrofuran solution of methyl bromide under stirring (180g of methyl bromide is poured into 315ml of tetrahydrofuran at -5°C--0°C), dissolve and set aside for use.

[0062] Step 2. Add 19.6g of lithium metal and 330ml of anhydrous tetrahydrofuran (moisture content less than 200ppm) into a 1000ml reaction bottle with mechanical stirring, and drop the temperature to -5°C to 0°C while stirring, and start adding the above mixed solution for about 2.5 hours After dripping, control the temperature at 5°C-15°C. After dripping, keep warm for 1.5 hours, then take a sample and add water to quench the reaction, then TLC (PE:EA=10:1, iodine color development, soaking in water), and send the sample to GC after passing the test (Central control 1), cool down to -10°C to -5°C.

[0063] Step 3, adding 4.5 g of phenothiazine and stirring for 20 min.

[0064] Step 4: Start adding 176g o...

Embodiment 3

[0070] Step 1. Dissolve 150g of adamantanone in 300ml of anhydrous benzene, and add 178g of 65% (wt / wt) methyl bromide in benzene solution under stirring (the methyl bromide is introduced into anhydrous benzene at -5°C--0°C ), ready to use after dissolving.

[0071] Step 2. Add 13g of lithium metal and 220ml of anhydrous benzene into a 1000ml reaction bottle with mechanical stirring, and drop the temperature to -5°C to 0°C while stirring, and start adding the above mixed solution dropwise for about 3 hours. Control the temperature at 5 ℃ ~ 15 ℃, keep warm for 1 hour after dripping, take samples and add water to quench the reaction, TLC (PE:EA=10:1, iodine color development, water soaking), and send samples to GC after passing the test (central control 1), Cool down to -10°C to -8°C.

[0072] Step 3: Add 1 g of phenothiazine and stir for 10 min.

[0073] Step 4: Start to drop 75g of acrylic anhydride to control the rate of addition and control the temperature at -10°C to -5°C...

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Abstract

The invention provides a preparation method of 2-methyl-2-adamantyl acrylate, which is characterized in that under low temperature condition, an active intermediate is formed by adamantane ketone and bromomethane under effect of lithium metal, and the active intermediate and acrylic anhydride are reacted to obtain 2-methyl-2-adamantyl acrylate. In the provided synthetic method, through the selection of reaction condition of each step, such as reaction temperature, reaction proportion, reaction time and reaction raw materials, and the problems of difficult purification, high cost, low reaction yield, low purity of product and inapplicable large scale industrial production in prior art can be overcome.

Description

technical field [0001] The invention relates to the field of organic synthesis, and in particular provides a preparation method of 2-methyl-2-adamantanyl acrylate. Background technique [0002] Adamantane is a regular, symmetrical and highly stable cage-like hydrocarbon. Because it has a structure in which four cyclohexane rings are condensed into a cage-like structure, it is a highly symmetrical and stable compound. It is known that its derivatives are involved in the fields of medicine, aerospace, functional materials, petroleum processing and so on. [0003] It is worth mentioning that adamantane has properties such as optical properties and heat resistance, so its derivatives are often used in optical disc substrates, optical fibers or lens lamps. It can be used as a photoresist for semiconductors, a sealing agent for optical semiconductors, optical and electronic components (light pipes, optical communication lenses, optical films, etc.) and their adhesives. [0004] ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/54
CPCC07C67/08C07C2603/74C07C69/54
Inventor 傅志伟
Owner XUZHOU B&C CHEM CO LTD
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