A kind of preparation method of 1-bromoadamantane

A technology of adamantane and bromination, which is applied in the field of preparation of 1-bromoadamantane, can solve the problems of large amount of three wastes, high cost, and easy volatilization of bromine, and achieve cost saving, reduction of discharge of three wastes, and inhibition of bromine Volatile effect

Active Publication Date: 2020-07-03
CHINA CATALYST HLDG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction of this method is a reversible reaction. In the synthesis process, because bromine is very volatile, it needs a lot of excess to ensure sufficient concentration; and after the reaction, there is a large amount of bromine remaining, which needs to be treated with sodium bisulfite solution. Large, serious environmental pollution; and this method has a significant defect that excessive bromine is not recycled, and the cost is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] A preparation method of 1-bromoadamantane, comprising the following steps:

[0023] Add 136g of adamantane to a 1L four-necked reaction flask, control the temperature in the flask to 15°C with an ice-water bath, then add dropwise a mixture of 952g of bromine (272g) and glacial acetic acid (680g) into the reaction flask, and after 2 hours of completion of the dropwise addition Raise the temperature to 40°C, at this time, gas is released, and keep warm at this temperature for 1h; Keep warm for 6 hours; after the heat preservation finishes, cool down to 70°C, adjust the pressure inside the bottle to be -0.1MPa, reclaim the mixed solution (698g) of bromine and glacial acetic acid by vacuum azeotropic distillation, and the content of bromine in the mixed solution is 15.3%; recover After the end, lower the temperature in the bottle to below 50°C, then add 450g of glacial acetic acid aqueous solution with a mass fraction of 80%, carry out cooling and crystallization, filter to...

Embodiment 2

[0027] A preparation method of 1-bromoadamantane, comprising the following steps:

[0028] Add 136g of adamantane to a 2L four-necked reaction flask, control the temperature in the flask to 15°C in an ice-water bath, then add a mixture of 1080g of bromine (360g) and glacial acetic acid (720g) dropwise into the reaction flask, and after 2 hours of dropping Raise the temperature to 40°C, at this time, gas is released, and keep warm at this temperature for 1h; Keep warm for 4 hours; after the heat preservation finishes, cool down to 70°C, adjust the pressure in the bottle to -0.1MPa, reclaim the mixed solution (800g) of bromine and glacial acetic acid by vacuum azeotropic distillation, and the content of bromine in the mixed solution is 18.6%; recover After the end, lower the temperature in the bottle to below 50°C, then add 500g of glacial acetic acid aqueous solution with a mass fraction of 80%, carry out cooling and crystallization, filter to obtain a filter cake, wash the fil...

Embodiment 3

[0030] A preparation method of 1-bromoadamantane, comprising the following steps:

[0031] Add 136g of adamantane to a 2L four-necked reaction flask, control the temperature in the flask to 15°C with an ice-water bath, then add a mixture of 1440g of bromine (360g) and glacial acetic acid (1080g) dropwise into the reaction flask, and after 2 hours of dropping Raise the temperature to 40°C, at this time, gas is released, and keep warm at this temperature for 1h; Keep warm for 6 hours; after the heat preservation finishes, cool down to 70°C, adjust the pressure inside the bottle to be -0.1MPa, reclaim the mixed solution (1162g) of bromine and glacial acetic acid by vacuum azeotropic distillation, and the content of bromine in the mixed solution is 13.36%; recover After the end, lower the temperature in the bottle to below 50°C, then add 400g of glacial acetic acid aqueous solution with a mass fraction of 70%, carry out cooling and crystallization, filter to obtain a filter cake, ...

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Abstract

The invention discloses a preparation method of 1-bromoadamantane. The method comprises the steps that diamantane is added into a reactor, the temperature inside the reactor is controlled to be 10-15 DEG C, then, a mixed solution of bromine and an organic solvent A is added dropwise into the reactor, dropping is completed in 1-3 h, then, the temperature is increased to 40 DEG C, the temperature is kept constant for 1 h, then, the temperature inside the reactor is gradually increased to 110 DEG C within 7 h in the 10 DEG C/h temperature programming mode, and after the temperature is kept constant for 4-6 h, reduced pressure distillation is performed to recycle a mixed solution of bromine and the organic solvent A; then, an organic solvent B is added into the reactor to perform cooling crystallization, after filtering, filter cakes are washed with distilled water till the pH value is 6-7, and airing is performed to obtain the 1-bromoadamantane. According to the method, in a bromination reaction, organic solvent glacial acetic acid (organic solvent A) is introduced, compared with a traditional method, on the premise that the reactions are not affected, the organic solvents are added to restrain volatilization of the bromine, the bromine can be effectively recycled, the recycling rate is larger than 90%, the cost is reduced, and discharge of waste gas, water and industrial residues is reduced.

Description

technical field [0001] The invention relates to a method for preparing 1-bromoadamantane, in particular to an industrial method for preparing adamantane, which can improve the utilization rate of bromine. Background technique [0002] 1-Bromoadamantane is an intermediate in the synthesis of amantadine hydrochloride, which is an antidrug that is effective in preventing and treating Asian A-2 influenza. In the pharmaceutical industry, there are very few domestic manufacturers, and the supply exceeds demand in the market. At present, the synthesis of amantadine by bromoadamantane is the main synthetic method in industry. The agent is at normal temperature and pressure, adamantane is added to the reactor, bromine about twice the weight of adamantane is added, and the temperature of the reactor is raised to 115 At about ℃, react in the bromination kettle for 24h-48h to generate bromoadamantane, add sodium bisulfite solution in the kettle to treat unreacted bromine, filter, wash,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C23/38C07C17/10
CPCC07C17/10C07C23/38
Inventor 李进李永宾严继业王庆吉王建青
Owner CHINA CATALYST HLDG CO LTD
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