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2,2,6,6-tetramethyl-4-piperidinamine preparation method

A technology of piperidine amine and compounds, which is applied in the field of chemical synthesis, can solve the problems of tightening safety and environmental protection policies, potential safety hazards, and high cost, and achieve the effects of eliminating potential safety hazards, reducing danger, and eliminating flammability

Active Publication Date: 2020-02-28
宿迁联盛科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The above two types of methods, although the electrolysis method is easy to control, has few by-products, and the products are easy to separate, but the equipment investment is high, the cost is large, and the large-scale production is limited by the scale of the electrolytic cell. limit
Moreover, the industrial production process is not yet very mature, and still needs to be explored
In the catalytic hydrogenation-amination reduction method, due to the presence of the raw material 2 , 2 , 6 , 6-tetramethylpiperidone, hydrogenation of 2 , 2, 6 , 6-tetramethylpiperidone is inevitable. The by-product tetramethylpiperidinol, and because it involves hydrogen and pressure reactions, there are always certain safety hazards, and the safety and environmental protection policies are increasingly tightened, and the hydrogenation process is restricted in some areas

Method used

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  • 2,2,6,6-tetramethyl-4-piperidinamine preparation method

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Embodiment 1

[0033] In a 500ml four-necked flask equipped with a thermometer, add 155g of 2,2,6,6-tetramethylpiperidone, 200g of water, install a condenser, control the temperature at 20-30°C, and control the pressure at 0-1Mpa. Pass 40g of liquid ammonia through the way of passing amine under the liquid, stir while passing through, and after stirring for 0.5 hours, raise the temperature to 50°C, use a dropping funnel to drop 160g of 50% mass fraction of formic acid aqueous solution, and keep it warm for 4 hours after dropping. Then the excess formic acid and solvent were evaporated by heating up, and then the product tetramethylpiperidinamine was obtained through rectification under reduced pressure, and the product yield was 92%.

Embodiment 2

[0035]Put 155g of 2,2,6,6-tetramethylpiperidone, 100g of water, and 100g of methanol into the autoclave at one time, then tighten the autoclave, replace with nitrogen for 3 times, and stir at 20-30°C, Pour in 50g of liquid ammonia, stir for half an hour, then pour in 184g of 50% formic acid aqueous solution, then raise the temperature to 90°C, control the pressure at 0.2-0.5Mpa, react for 3 hours, then cool down. The reaction solution was transferred to a flask, and then rectified after desolvation to obtain the product tetramethylpiperidinamine with a product yield of 94%.

Embodiment 3

[0037] Put 155g of 2,2,6,6-tetramethylpiperidone, 100g of methanol, and 130g of n-butylamine into the autoclave at one time, then tighten the autoclave, replace with nitrogen for 3 times, and stir at 40-50°C for 1 hour , and then pass 54g of formic acid aqueous solution with 85% mass fraction, raise the temperature to 120°C, the pressure does not exceed 2Mpa, stir and keep warm for 4 hours, then cool down to remove the solvent from the reaction solution, and finally vacuum distill the product N-butyl-2,2 , 6,6-tetramethyl-4-piperidinamine, the product yield is 92%.

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Abstract

The invention relates to a 2,2,6,6-tetramethyl-4-piperidinamine preparation method, which comprises: adding a raw material 2,2,6,6-tetramethylpiperidone, an amine reactant and a solvent into a reaction kettle, stirring and premixing at 10-50 DEG C to form an imine intermediate, reducing the imine intermediate by using a reducing agent at a certain temperature under a certain pressure, and reactingfor a certain time to finally synthesize the target product 2,2,6,6-tetramethyl-4-piperidinamine compound. According to the invention, 2,2,6,6-tetramethyl-4-carbonyl piperidone reacts with an amine compound to generate an imine intermediate, and a reducing agent is used for replacing catalytic hydrogenation to perform reduction, so the product yield can reach more than 92%, the generation of the2,2,6,6-tetramethylpiperidone hydrogenation byproduct tetramethylpiperidinol is avoided, the hydrogenation process with a high risk coefficient is avoided, and the method is an ideal process for achieving industrialization.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing tetramethylpiperidine amine compounds, intermediates of hindered amine light stabilizers. Background technique [0002] 2,2,6,6-Tetramethyl-4-piperidinamine compound is an important hindered amine light stabilizer intermediate. It is mainly used in the synthesis of bonded and polymer hindered amine light stabilizers. [0003] At present, there are mainly two methods for the preparation of tetramethylpiperidine amine compounds, one of which is a catalytic hydrogenation-ammoniation reduction method, and the other is an electrochemical method. [0004] For the catalytic hydrogenation-amination reduction method: [0005] Tianda Huang Hongmei Wenwen (Huang Hongmei, Wang Duolu, Chen Ligong, et al. Synthesis of 2,2,6,6-tetramethyl-4-piperidinamine by catalytic amination method[J]. Journal of Tianjin University: Natural Science and Engi...

Claims

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Application Information

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IPC IPC(8): C07D211/58
CPCC07D211/58
Inventor 袁开锋刘恩静周超杨紫伟胡新利
Owner 宿迁联盛科技股份有限公司
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