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Preparation method of norbornane dimethyl amine

A technology for bornane dimethylamine and compounds is applied in the field of preparation of norbornane dimethylamine, and can solve the problems of complicated methods, complicated operations, complicated post-processing and the like

Active Publication Date: 2020-04-14
SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the above-mentioned preparation scheme, method (1) uses hydrogen cyanide in the process of manufacturing norbornane dimethylamine, because hydrogen cyanide is highly toxic, and its boiling point is low, and the explosion limit in air is 5.6%~12.8% %, very prone to dangerous deposits; and method (2) has used an expensive rhodium catalyst in the process of manufacturing norbornane dimethylamine, and also needs to be used in conjunction with other ligands, and the method is more complicated
In addition, the post-processing of the above two methods is relatively complicated, and there are problems of low yield and complicated operation.

Method used

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  • Preparation method of norbornane dimethyl amine
  • Preparation method of norbornane dimethyl amine
  • Preparation method of norbornane dimethyl amine

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preparation example Construction

[0026] The invention provides a kind of preparation method of norbornane dimethylamine, comprises the following steps:

[0027] a) The compound of the structure shown in formula (I) is mixed with urotropine, acid and the first solvent, and the first reaction is carried out to obtain the first reaction mixture; then the above-mentioned first reaction mixture is sequentially neutralized, the second Once filtered, the filtrate obtained is purified for the first time to obtain a compound of structure shown in formula (II);

[0028]

[0029]

[0030] b) Mix the structural compound shown in formula (II) obtained in step a) with hydrogen, a catalyst, and a second solvent, and perform a second reaction to obtain a second reaction mixture; then filter the above-mentioned second reaction mixture for the second time , The obtained filtrate was purified for the second time to obtain norbornane dimethylamine.

[0031] In the present invention, firstly, the compound of the structure ...

Embodiment 1

[0052] (1) Weigh 9.21g of norbornadiene into a 500mL single-necked flask, add 9.81g of urotropine, 64.47g of sulfuric acid, and 138.15g of acetone in sequence, and react for 15h in an oil bath at T=70°C. The sodium carbonate solution system is adjusted to neutrality, then filter, obtain the filtrate that contains the structure compound shown in formula (II);

[0053]

[0054] Then in the separatory funnel, the filtrate is layered to obtain the organic phase, and then the organic phase is rotary evaporated to obtain 13.82g norbornene dimethylamine; the above steps are repeated to obtain more target products, and a total of 27.63g norbornene is obtained ethylene dimethylamine.

[0055] (2) Weigh 15.02g of norbornene dimethylamine obtained in step (1) in a 500mL autoclave, add 1.05g of palladium carbon and 376.25g of toluene successively therein, then pressurize to 0.7MPa with hydrogen and Keep this pressure in the middle, raise the temperature to 95°C and react for 5h, filte...

Embodiment 2

[0059] (1) Weigh 9.21g of norbornadiene into a 250mL single-necked flask, add 5.61g of urotropine, 36.84g of acetic acid, and 92.1g of acetonitrile in sequence, and react for 10h in an oil bath at T=50°C. After the reaction is completed, use saturated The sodium carbonate solution system is adjusted to neutrality, then filter, obtain the filtrate that contains the structure compound shown in formula (II);

[0060]

[0061] Then in the separatory funnel, the filtrate is layered to obtain the organic phase, and then the organic phase is rotary evaporated to obtain 14.27g norbornene dimethylamine; the above steps are repeated to obtain more target products, and a total of 28.55g norbornene is obtained ethylene dimethylamine.

[0062] (2) Weigh 15.02g of norbornene dimethylamine obtained in step (1) in a 500mL autoclave, add 1.05g of Raney nickel and 376.25g of methanol successively therein, then pressurize to 0.9MPa with hydrogen and react During the process, the pressure was...

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Abstract

The invention provides a preparation method of norbornane dimethyl amine. The preparation method comprises the following steps: a) mixing a compound with a structure as shown in a formula (I) with urotropin, an acid and a first solvent, and carrying out primary reaction to obtain a first reaction mixture; neutralizing and filtering the first reaction mixture for the first time in sequence, and purifying the obtained filtrate for the first time to obtain a compound with a structure shown in a formula (II); b) mixing the compound with the structure shown in the formula (II) obtained in the stepa) with hydrogen, a catalyst and a second solvent, carrying out a second reaction to obtain a second reaction mixture; filtering the second reaction mixture for the second time, and purifying the obtained filtrate for the second time to obtain norbornane dimethyl amine. Compared with the prior art, the preparation method provided by the invention has the advantages that the use of hydrogen cyanide, rhodium catalysts and other ligands can be avoided, the method is simple, the operation is easy, the product yield is high, and the application prospect is wide.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, and more specifically, relates to a preparation method of norbornane dimethylamine. Background technique [0002] Norbornane dimethylamine, also known as norbornane dimethylamine, is often used as a curing agent for epoxy resins. It can be cured quickly even at low temperatures, and the cured product has excellent strength, flexibility, heat deformation resistance, and impact resistance. , weather resistance, chemical resistance and yellowing resistance are excellent performance. [0003] At present, the preparation method of norbornane dimethylamine in the prior art comprises: [0004] (1) Publication number is the patent of CN101443308A, and it discloses the manufacture method of dicyano norbornane and the zero-valent nickel coordination compound catalyst, is the raw material manufacture norbornane dimethylamine with norbornane dinitrile; But norbornane Dinitrile is synthes...

Claims

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Application Information

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IPC IPC(8): C07C211/19C07C209/00C07C209/84
CPCC07C209/00C07C209/84C07C2602/42C07C211/19
Inventor 翟宏斌任永平梁万根张超崔卫华费潇瑶
Owner SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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