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Method for synthesizing 1, 3-adamantane diamine

A synthetic method, the technology of adamantane, applied in the field of synthesis of 1,3-adamantanediamine, can solve the problems of expensive raw materials and catalysts, high risk of reagents, etc., achieve mild conditions, easy access to raw materials, and realize industrial production Effect

Inactive Publication Date: 2013-12-11
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of this method is relatively high, but the reagents used are highly dangerous, and the raw materials and catalysts are expensive.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 2.94g (10mmol) 1,3-dibromoadamantane, 1.2g (20mmol) urea, and 1.5g isophorone into a 100ml three-necked flask, heat in an oil bath to 180°C, and stir for 1.5h. Cool the reaction mixture to 50°C, add 120ml of 1M hydrochloric acid solution and stir for 30min, then remove insoluble impurities by suction filtration, add sodium hydroxide solution with a mass fraction of 40% to the filtrate to neutralize until the solution is alkaline, use 100ml Carbon tetrachloride was extracted, the solvent was distilled off under reduced pressure, and the obtained solid was vacuum-dried at 60°C. The quality of the obtained product was 1.07g, and the yield was 66.00%.

Embodiment 2

[0028] Add 2.94g (10mmol) 1,3-dibromoadamantane, 3.0g (50mmol) urea, and 12g diphenyl ether into a 100ml three-neck flask, heat in an oil bath, raise the temperature to 100°C, stir and react for 15h, and cool the reaction mixture to 50°C, add 40ml 3M hydrochloric acid solution and stir for 30min, then remove insoluble impurities by suction filtration, add sodium hydroxide solution with a mass fraction of 40% to the filtrate to neutralize the solution until the solution is alkaline, extract with 120ml dichloroethane, reduce The solvent was removed by distillation under pressure, and the obtained solid was vacuum-dried at 60° C. The product quality was 1.17 g, and the yield was 70.48%.

Embodiment 3

[0030] Add 2.94g (10mmol) 1,3-dibromoadamantane, 1.80g (30mmol) urea, and 18g dibutyl phthalate into a 100ml three-necked flask, heat in an oil bath, raise the temperature to 145°C, and stir for 8 hours. Cool the reaction mixture to 50°C, add 20ml of 6M hydrochloric acid solution and stir for 30min, then remove insoluble impurities by suction filtration, add sodium hydroxide solution with a mass fraction of 40% to the filtrate to neutralize the solution until the solution is alkaline, add 80ml of chlorobenzene Extraction, the solvent was distilled off under reduced pressure to obtain a white solid, and the resulting solid was vacuum-dried at 60°C. The quality of the obtained product was 1.11g, and the yield was 68.87%.

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Abstract

The invention discloses a method for synthesizing 1, 3-adamantane diamine. The 1, 3-adamantane diamine synthesized by the method is prepared by the following steps of: performing amination on 1, 3-dibromoadamantane and urea in a high boiling point solvent; and performing separated purification through acidification, neutralization and extraction. The method particularly comprises the following steps of: mixing the 1,3-dibromoadamantane and the urea uniformly according to the molar ratio of the 1,3-dibromoadamantane to the urea of 1:2-10; adding the high boiling point solvent; heating the mixture to a preset temperature in an oil bath and reacting under stirring; after the reaction is finished, cooling to 50 DEG C; adding hydrochloric acid and stirring to dissolve the product; filtering to remove insoluble impurities; adding sodium hydroxide solution into filtrate to neutralize; adding an excessive organic solvent to perform extraction; distilling the obtained extract liquid under reduced pressure to remove the solvent; and performing vacuum drying to obtain the product 1,3-adamantane diamine. The method has the advantages of short reaction route, simpleness and convenience in operation, mild condition, clean and environmentally-friendly process, high product yield and the like.

Description

technical field [0001] The invention relates to a synthesis method of 1,3-adamantanediamine. Adamantanediamine is currently mostly used in polymer monomers, and polymers containing 1,3-adamantanediamine can be used in microelectronics, gas separation, etc. have potential medical value. Background technique [0002] 1,3-Adamantanediamine has important applications in the fields of polymer materials, fine chemicals, electronics, and medicine because it contains both a rigid adamantane cage structure and a highly active amine group. In the field of synthetic polymer materials, 1,3-adamantanediamine can be used to synthesize polyimide-based gas separation membrane materials with excellent performance, and can be used to synthesize organic light-emitting materials with high thermal stability, and can also be used as a polymerization monomer Or modifying groups are introduced into other polymer materials to change their thermal stability and hydrothermal stability; in fine chemi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/38C07C209/08
Inventor 郭建维朱华钟星付长安蔡璐马倩彭进平崔亦华邓志城
Owner GUANGDONG UNIV OF TECH
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