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Synthesis method of 1,4-butanediamine

A synthetic method and the technology of butanediamine, which are applied in the field 1, can solve the problems of unsafe industrial production, failure to meet energy saving and emission reduction, and high process operation requirements, and achieve maximum implementation value and social and economic benefits, facilitate industrial production, and process conditions easy effect

Active Publication Date: 2010-06-16
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still some problems in the production process of the appeal process, for example, high hydrolysis temperature and high pressure; diazonium salt heating releases a large amount of nitrogen, which is easy to cause explosion, industrial production is extremely unsafe, and the process operation requirements are relatively high; raw materials are expensive and the reaction It is easy to produce "three wastes", easy to pollute the environment, not conducive to labor protection, and not in line with the industrial policy of energy conservation and emission reduction, etc.

Method used

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  • Synthesis method of 1,4-butanediamine
  • Synthesis method of 1,4-butanediamine
  • Synthesis method of 1,4-butanediamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Weigh 10.90g (0.05mol) of 1,4-dibromobutylamine, add it to a 500ml three-neck flask, add 200mL acetone, stir at 70°C, add 22.20g (0.12mol) potassium phthalimide, and reflux reaction After 14 hours, TLC detected that the reaction reached the end point, and the reaction solution was suction filtered to obtain a white insoluble matter, which was washed twice with 20 ml of distilled water and then dried to obtain 15.66 g of 1,4-diphthalimide butane. 90%, mp.227-229°C. Add 15.66g (0.045mol) of 1,4-diphthalimidebutane prepared in the previous step to a 250mL three-neck flask, add 100mL of ethanol, and then add 18.90g of 40% methylamine aqueous solution (containing methylamine The number of moles of the amine is 0.24 mol), heated until the solid is completely dissolved, and continued to stir until the reaction solution was yellow and transparent, then added 8 mL of concentrated hydrochloric acid, and continued to reflux for 4 hours to end the reaction. The reaction product wa...

Embodiment 2

[0024]Weigh 10.90g (0.05mol) of 1,4-dibromobutylamine, add it to a 500ml three-necked flask, add 200mL of ethanol, stir at 70°C, add 22.20g (0.12mol) of potassium phthalimide, and reflux After 15 hours, TLC detected that the reaction reached the end point, and the reaction solution was suction filtered to obtain a white insoluble matter, which was washed twice with 20 ml of distilled water and then dried to obtain 11.23 g of 1,4-diphthalimide butane. 72.3%, mp.227-229°C. Add 12.58g (0.036mol) of 1,4-diphthalimidebutane prepared in the previous step to a 250mL three-necked flask, add 100mL of ethanol, and then add 16.81g of 40% methylamine aqueous solution (containing The molar weight of methylamine is 0.21mol), heated until the solid is completely dissolved, and continuously stirred until the reaction solution is yellow and transparent, then 8ml of concentrated hydrochloric acid is added, and the reaction is terminated after continuing to reflux for 4 hours. The reaction prod...

Embodiment 3

[0026] Weigh 10.90g (0.05mol) of 1,4-dibromobutylamine, add it to a 500ml three-neck flask, add 200mL methanol, stir at 70°C, add 22.20g (0.12mol) potassium phthalimide, and reflux After 12 hours, TLC detects that the reaction reaches the end point, and the reaction solution is suction filtered to obtain a white insoluble matter, which is washed twice with 20 ml of distilled water and then dried to obtain 11.23 g of 1,4-diphthalimide butane. 64.5%, mp.227-229°C. Add 11.23g (0.032mol) of 1,4-diphthalimidebutane prepared in the previous step to a 250mL three-necked flask, add 100mL of ethanol, and then add 14.99g of 40% methylamine aqueous solution (containing methylamine The molar weight of the amine is 0.19 mol), heated until the solid is completely dissolved, and continuously stirred until the reaction solution is yellow and transparent, then 8ml of concentrated hydrochloric acid is added, and the reaction is terminated after continuing to reflux for 4 hours. The reaction pr...

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Abstract

The invention provides a synthesis method of 1,4-butanediamine, which comprises the steps of: (a) dissolving the 1,4-dibromobutyl amine represented by formula (1) in a solvent A, adding the phthalimide potassium represented by formula (2), reacting while stirring at a reflux temperature, filtering reaction liquid, washing by using distilled water to obtain the 1,4-diphthalimide butane representedby formula (3); (b) adding the 1,4-diphthalimide butane obtained in the step (1) and 40% methylamine water solution to a solvent B, heating until solids are dissolved completely, stirring and reacting for 0.5-4 hours at the reflux temperature to obtain reaction products; and (c) filtering the reaction products, post-treating filtrate, distilling the filtrate under normal pressure, and collecting the fractions between 158 DEG C and 160 DEG C to obtain the 1,4-butanediamine. The invention has simple and convenient technological conditions, cheap raw materials, mild reaction conditions, easy control and convenient industrial production.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing 1,4-butanediamine. (2) Background technology [0002] 1,4-Butanediamine, also known as 1,4-diaminobutane, tetramethylenediamine, carnitine, English name 1,4-Diaminobutane. [0003] [0004] 1,4-butanediamine is a kind of important chemical intermediate, for example, has the development prospect drug detoxification drug agmatine sulfate, is exactly synthesized with 1,4-butanediamine as main raw material (Chinese open patent CN1834085A and CN101121677). As another example, some major engineering plastics (polyamide-4,6, in the form of homopolymer or copolymer) are also synthesized using 1,4-butanediamine as an important raw material. Therefore, 1,4-butanediamine has broad market prospects. [0005] Regarding the synthesis of 1,4-butanediamine, many countries have carried out research and development on its synthetic method, and the chemical synthesis methods integrated mainly contain the follow...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/09C07C209/62
Inventor 单伟光叶珊珊王建伟占扎君唐岚侯晓蓉于海宁
Owner ZHEJIANG UNIV OF TECH
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