Method for preparing monomer of temperature-sensitive polyisopropylacrylamide

A technology of propylacrylamide and temperature-sensitive type, which is applied in the field of monomer preparation of temperature-sensitive polyisopropylacrylamide, can solve the problems of violent reaction, severe heat release, poor selectivity, etc., and achieve the product with less impurity content, The order of addition is simple and the effect of reducing reaction toxicity

Active Publication Date: 2008-08-13
RONGHAI SUPERSONIC MEDICINE EN
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein Chen Wenming etc. report {see Chen Wenming, Yu Zhenning, Yan Lifeng: The acid-catalyzed synthesis improvement of N-isopropylacrylamide and N-isopropylmethacrylamide, [J]. Fine Chemical Industry, 1998, (6 )} the synthetic method of NIPA of acrylonitrile and isopropanol in the presence of concentrated sulfuric acid, the method has requirements on the sulfuric acid consumption, feeding sequence, temperature and pH value of the reaction stage, the follow-up separation and extraction is complicated, and is not suitable for mass production
The Beckman rearrangement synthesis method is to directly react amines and acryloyl chloride (ACC) to obtain NIPA, which is violent and exothermic, and NIPA is easy to polymerize during synthesis, and the yield is low, and various N-substituted amides will be produced By-products, poor selectivity, the synthesis of NIPA from reported isopropylamine (IPA) and acryloyl chloride (ACC) is more complex and costly
French patent FR2498182 and U.S. patent US4835312 introduce the method of synthesizing NIPA by reacting acrylamide and bromopropane, and the yield is only 65%. Due to the influence of impurities mixed in the product, the monomer will change color during long-term use. thereby affecting the quality

Method used

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  • Method for preparing monomer of temperature-sensitive polyisopropylacrylamide
  • Method for preparing monomer of temperature-sensitive polyisopropylacrylamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Equipment: 2000ml four-necked bottle (reaction kettle), rotary evaporator, electric heater, water bath, glass thermometer, perforated rubber stopper, vacuum dryer, separating funnel, Erlenmeyer flask;

[0033] Raw materials: ethyl acetate, isopropylamine, acryloyl chloride, 4-methoxyphenol, n-hexane

[0034] step:

[0035] 1) In a 2000ml four-neck bottle, add 950ml ethyl acetate, then add 160g isopropylamine, and add the polymerization inhibitor 4-methoxyphenol, the amount is 0.5g, and cool it to below 5°C with ice water.

[0036] 2) Add 117g of acryloyl chloride diluted with 300ml of ethyl acetate dropwise, and keep the reaction below 5°C.

[0037] 3) After dropping, react for 12 hours, keep the reaction below 5°C, that is, stir in an ice-water bath for 12 hours.

[0038] 4) After the reaction is completed, filter and remove the precipitate to obtain about 1200 ml of isopropylamine hydrochloride solution, and add 0.3 g of polymerization inhibitor 4-methoxyphenol to t...

Embodiment 2

[0043] Equipment and raw materials: 2L four-necked bottle (reaction kettle), rotary evaporator, electric heater, water bath, glass thermometer, perforated rubber stopper, vacuum dryer, separating funnel, Erlenmeyer flask;

[0044] Raw materials: ethyl acetate, isopropylamine, acryloyl chloride, 4-methoxyphenol, n-hexane

[0045] step:

[0046] 1) In a 2L four-neck bottle, add 1000ml of ethyl acetate, then add 80g of isopropylamine, and add 0.2g of polymerization inhibitor 4-methoxyphenol, and cool it to below 5°C with ice water.

[0047] 2) Add 57.5 g of acryloyl chloride diluted with 300 ml of ethyl acetate dropwise, and keep the reaction below 5°C.

[0048] 3) After dripping, react for 12 hours and keep the reaction below 5°C.

[0049] 4) After the reaction is completed, about 1350 ml of isopropylamine hydrochloride solution is obtained by filtration, and 0.1 g of polymerization inhibitor 4-methoxyphenol is added to the solution.

[0050] 5) Ethyl acetate was removed by r...

Embodiment 3

[0054] Equipment: 2L four-necked bottle (reaction kettle), rotary evaporator, electric heater, water bath, glass thermometer, perforated rubber stopper, vacuum dryer, separating funnel, Erlenmeyer flask;

[0055] Raw materials: ethyl acetate, isopropylamine, acryloyl chloride, 4-methoxyphenol, n-hexane

[0056] step:

[0057] 1) In a 2L four-necked bottle, add 1000ml of ethyl acetate, then add 240g of isopropylamine, and add 1.0g of polymerization inhibitor 4-methoxyphenol, and cool it to below 5°C with ice water.

[0058] 2) Add dropwise 175g of acryloyl chloride diluted with 500ml of ethyl acetate, and keep the reaction below 5°C.

[0059] 3) After dripping, react for 12 hours and keep the reaction below 5°C.

[0060] 4) After the reaction is completed, about 1000 ml of isopropylamine hydrochloride solution is obtained by filtration, and 0.5 g of polymerization inhibitor 4-methoxyphenol is added to the solution.

[0061] 5) Ethyl acetate was removed by rotary evaporation ...

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Abstract

The invention belongs to the chemical synthesis technology field, particularly relates to a temperature-sensitive poly(N-isopropylacrylamide) monomer preparing method. The method comprises steps of: (1) respectively adding isopropyl amine and acryloyl chloride into ethyl acetate solvent; (2) adding sollution of acryloyl chloride and ethyl acetate into sollution of isopropyl amine and ethyl acetate to perform synthesis reaction; (3) after the synthesis reaction, filtering to obtain isopropyl amine hydrochloride solution; (4) adding inhibitors; (5) rotating and vaporizing the sollution to remove ethyl acetate solvent, obataining crude products of N-isopropylacrylamide; (6) adding the extraction agent n-hexane, cooling to obtain white crystal N-isopropylacrylamide monomer; (7) vacuum-drying to obain N-isopropylacrylamide monomer products. The invention is free of strong acid, the feeding sequence is simple, the reaction temperature is easy to control, the subsequent separation and purification operation is simple. The invention also has the advantages of small by-products, good selectivety, simple process, high yield and low cost.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a monomer preparation method of temperature-sensitive polyisopropylacrylamide. Background technique [0002] Polymer gel is a soft and wet material with both liquid and solid properties. It is a multi-component system composed of a three-dimensional cross-linked network of polymers and a small molecule solvent fixed in it. It is a cross-linked polymer swelling body that cannot be melted and has certain elasticity. The material responds softly to changes in the environment, such as pH, temperature, light intensity, stimuli such as electric and magnetic fields, and chemicals. In recent years, research work on intelligent polymer gels is being carried out, and it has attracted much attention in the fields of medicine, pharmacy, life sciences, bioengineering, electronics and mechanical components. The temperature-sensitive gel is a kind of intelligent polymer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/09C07C231/02
Inventor 田耘博王智彪叶方伟
Owner RONGHAI SUPERSONIC MEDICINE EN
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