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Method for synthesizing N,N-dimethylaminopropyl acrylamide by utilizing decarboxylation reaction

A technology of dimethylaminopropylacrylamide and dimethylaminopropylamine, which is applied in the field of preparation of N,N-dimethylaminopropylacrylamide, can solve problems such as no solution, and achieve production safety and reaction The effect of mild conditions

Inactive Publication Date: 2021-04-06
WUXI HIT SAINT OPTOELECTRONICS MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004]There is currently no solution for the shortcomings of existing technologies

Method used

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  • Method for synthesizing N,N-dimethylaminopropyl acrylamide by utilizing decarboxylation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 1 mol of maleic anhydride to 1000 mL of ethyl acetate after dehydration and start stirring, drop in 1 mol of 3-dimethylaminopropylenediamine and keep it at 40°C for 2 hours. After the reaction, heat up and distill off the solvent to obtain the bottom liquid (Intermediate product) 180.5g, purity 96.4%, reaction conversion rate 91.7%, then the obtained intermediate, add reactant 2g pyridinethiol solvent, add catalyst 0.5gDCC and 0.5gDMAP, react at 30°C for 3h, then add 0.5g three Butyltin, 0.25g AIBN, and 0.25g p-tert-butylphenol were reacted at 70°C for 2 hours. After the reaction was completed, 105.1g of N,N-dimethylaminopropylacrylamide was obtained with a purity of 98.6%. The decarboxylation yield is 65.67%, and the comprehensive yield is 69.7%.

Embodiment 2

[0022] Add 1 mol of maleic anhydride to 1000 mL of ethyl acetate after dehydration and start stirring, drop in 1 mol of 3-dimethylaminopropylenediamine and keep it at 40°C for 2 hours. After the reaction, raise the temperature and evaporate the solvent to obtain the bottom liquid (Intermediate product) 190.1g, purity 98.7%, reaction conversion rate 93.8%, then the obtained intermediate, add reactant 3g pyridinethiol, then add catalyst 1gDCC and 1gDMAP, react at 40°C for 4h, then add 1g three Butyltin, 0.5g AIBN, and 0.5g p-tert-butylphenol were reacted at 80°C for 3 hours. After the reaction was completed, 118.6g of N,N-dimethylaminopropylacrylamide was obtained with a purity of 98.7%. The decarboxylation yield was 79.88%, and the comprehensive yield was 75.9%.

Embodiment 3

[0024] Add 1 mol of maleic anhydride to 1000 mL of ethyl acetate after dehydration and start stirring, drop in 1 mol of 3-dimethylaminopropylenediamine and keep it at 40°C for 2 hours. After the reaction, heat up and distill off the solvent to obtain the bottom liquid (Intermediate product) 195.3g, purity 99.5%, reaction conversion rate 94.7%, then the obtained intermediate, add reactant 5g pyridinethiol, then add catalyst 2gDCC and 2gDMAP, react at 50°C for 5h, then add 2g three Butyl tin, 1g AIBN, and 1g p-tert-butylphenol were reacted at 90°C for 4h. After the reaction was completed, 121.5g of N,N-dimethylaminopropyl acrylamide was obtained with a purity of 98.4%. The yield was 82.76%, and the comprehensive yield was 79.8%.

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Abstract

The invention discloses a method for synthesizing N,N-dimethylaminopropylacrylamide by utilizing a decarboxylation reaction. The method is characterized by comprising the following steps: dropwisely adding 3-dimethylaminopropylamine into a mixed solution of maleic anhydride and a solvent, stirring, reacting to obtain an intermediate, adding catalysts DMAP and DCC into the intermediate, reacting to produce Barton ester, adding a catalytic amount of tributyltin, AIBN and a polymerization inhibitor, carrying out a reaction to remove one molecule of CO2, and carrying out reduced pressure distillation to obtain a high-purity product. According to the invention, a low-temperature reaction route is used, reaction conditions are mild, and production is safer.

Description

technical field [0001] The invention relates to the synthesis of N,N-dimethylaminopropylacrylamide, in particular to a preparation method of N,N-dimethylaminopropylacrylamide with mild reaction conditions. Background technique [0002] N,N-Dimethylaminopropylacrylamide (DMAPAA for short) is widely used in water treatment, household chemicals, papermaking, medicine, fiber industry, oil and gas development, synthesis of photosensitive materials, and auxiliary agent in printing industry , leather processing additives, etc. DMAPAA is a fluid liquid at room temperature. Due to the presence of tertiary amine groups and vinyl groups in its molecular structure, it can generate quaternary ammonium salts or undergo polymerization reactions to generate various compounds. DMAPAA has high activity as a monomer, and the relative molecular weight of the generated polymer is large. It is alkaline and cationic, and has good water solubility and alcohol solubility. It can be widely used as t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C231/12C07C233/38C07D213/89
CPCC07C231/02C07C231/12C07D213/89
Inventor 杨恺
Owner WUXI HIT SAINT OPTOELECTRONICS MATERIAL TECH CO LTD