Method for preparing DMAPPA (N-(3-dimethyl aminopropyl) acrylamide) through catalytic amidation

A dimethylaminopropyl, catalytic amide technology, applied in the preparation of carboxylic acid amides, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of reduced catalytic activity, low flash point temperature, potential safety hazards, etc. Good quality, good selectivity, convenient storage and transportation

Inactive Publication Date: 2016-03-30
SHENYANG RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the poisonous effect of methanol on the human body and the low flash point temperature, this process uses methanol as a solvent for the reaction, which has great safety haz

Method used

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  • Method for preparing DMAPPA (N-(3-dimethyl aminopropyl) acrylamide) through catalytic amidation
  • Method for preparing DMAPPA (N-(3-dimethyl aminopropyl) acrylamide) through catalytic amidation
  • Method for preparing DMAPPA (N-(3-dimethyl aminopropyl) acrylamide) through catalytic amidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Add 173.7kg of methyl acrylate, 517.2kg of N,N-dimethyl-1,3-propylenediamine, 13.8kg of dibutyltin oxide and 0.69kg of hydroquinone into the reactor, stir and heat up to 150 ℃ for 12 hours, then lower the temperature to 120 ℃, and distill off excess N,N-dimethyl-1,3-propanediamine and methanol under reduced pressure at 10mmHg, and the remaining material in the kettle is the intermediate product N-diamine Methylaminopropyl-β-dipropylaminoacrylamide. Excess N,N-dimethyl-1,3-propanediamine and methanol are separated through a distillation tower, and the recovered raw material N,N-dimethyl-1,3-propanediamine is put back into the reaction.

[0033] (2) Transfer 494kg of the above-mentioned intermediate product into a distillation reactor, reduce the pressure to 5mmHg, stir and heat up to 230°C, and carry out distillation treatment on the intermediate product. The distillate contains the raw material N,N-dimethyl-1,3 -Propylenediamine and the product N-(3-dimethylaminopr...

Embodiment 2

[0036] (1) Add 173.7kg of methyl acrylate, 413.7kg of N,N-dimethyl-1,3-propylenediamine, 5.87kg of dibutyltin dilaurate and 1.17kg of p-hydroxyanisole into the reactor, and stir Raise the temperature to 170°C and keep it for 10 hours, then lower the temperature to 140°C, distill off excess N,N-dimethyl-1,3-propanediamine and methanol under reduced pressure at 17mmHg, the remaining material in the kettle is the intermediate product N-Dimethylaminopropyl-β-dipropylaminoacrylamide. Excess N,N-dimethyl-1,3-propanediamine and methanol are separated through a distillation tower, and the recovered raw material N,N-dimethyl-1,3-propanediamine is put back into the reaction.

[0037] (2) Transfer 487.9kg of the above-mentioned intermediate product into a distillation reactor, reduce the pressure to 12mmHg, stir and heat up to 260°C, and carry out distillation treatment on the intermediate product. The distillate contains the raw material N,N-dimethyl-1, 3-propanediamine and the product...

Embodiment 3

[0040] (1) 173.7kg methyl acrylate, 342.9kg N,N-dimethyl-1,3-propylenediamine, recovered 174.3kgN,N-dimethyl-1,3-propylenediamine, recovered 10.1kg Dibutyltin oxide and add 3.7kg of new dibutyltin oxide, and 1.73kg of p-tert-butylphenol into the reaction kettle, stir and heat up to 190°C for 8 hours, then cool down to 160°C, under 25mmHg Excessive N,N-dimethyl-1,3-propanediamine and methanol are evaporated under reduced pressure, and the remaining material in the kettle is the intermediate product N-dimethylaminopropyl-β-dipropylaminoacrylamide. Excess N,N-dimethyl-1,3-propanediamine and methanol are separated through a distillation tower, and the recovered raw material N,N-dimethyl-1,3-propanediamine is put back into the reaction.

[0041] (2) Transfer 497.5kg of the above-mentioned intermediate product into a distillation reactor, reduce the pressure to 15mmHg, stir and heat up to 280°C, and carry out distillation treatment on the intermediate product. The distillate contain...

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Abstract

The invention belongs to the field of organic synthesis and particularly relates to a method for preparing DMAPPA (N-(3-dimethyl aminopropyl) acrylamide) through catalytic amidation. According to the method, methyl acrylate, N,N-dimethyl-1,3-propanediamine, a catalyst and an inhibitor are added to a reaction kettle, stirred, heated and cooled, excessive solvent is steamed out, an intermediate product is subjected to reduced pressure distillation treatment, then a distillate is added to a fractionating tower, reduced-pressure heating is performed for collection of a product distillate, and DMAPPA with the purity higher than or equal to 98% is obtained. The process developed with the method is simple and convenient to operate, a few reaction steps are included, and the raw material methyl acrylate is low in cost, easy to obtain and convenient to store and transport; methyl alcohol is generated in a reaction process, so that the reaction temperature is reduced, reaction conditions are mild, and side reactions are reduced; the novel catalyst is selected, accordingly, the reaction speed is high, the yield is high, the product quality is good, polymerization in a tower due to high temperature and high material activity in a distillation process is avoided, and three wastes are hardly generated.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing N-(3-dimethylaminopropyl)acrylamide by catalytic amidation. Background technique [0002] The new functional compound N-(3-dimethylaminopropyl) acrylamide (DMAPAA for short) is a fluid liquid at room temperature and is an unsaturated tertiary amine. It is mainly used as a polymer monomer, oilfield water injection agent, flocculation additives, papermaking additives, dispersants, coating additives, pharmaceutical intermediates, etc. The compound has a tertiary amine group and a vinyl group in its structure. It has high monomer activity, is alkaline and has cationic characteristics. It has the characteristics of forming quaternary ammonium salts and polymerizing reactions. It has broad market prospects both at home and abroad. Because the synthesis conditions of this monomer are very harsh, the domestic market mainly relies on imports to meet the...

Claims

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Application Information

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IPC IPC(8): C07C233/38C07C231/12
CPCC07C231/02C07C231/12C07C237/10C07C233/38
Inventor 王玉灿马瑛孟明扬刘东高嘉新
Owner SHENYANG RES INST OF CHEM IND
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