Synthesis method for betaine-type amphoteric ion compound containing reactive group

A zwitterion, synthesis method technology, applied in the preparation of organic compounds, chemical instruments and methods, cyanide reaction preparation and other directions, can solve problems such as inappropriate use, carcinogenicity, etc., and achieve the advantages of less side reactions, simple implementation, and reduced synthesis costs. Effect

Inactive Publication Date: 2013-09-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the raw material sultone has carcinogenic effect on organisms, so it should not be used

Method used

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  • Synthesis method for betaine-type amphoteric ion compound containing reactive group
  • Synthesis method for betaine-type amphoteric ion compound containing reactive group
  • Synthesis method for betaine-type amphoteric ion compound containing reactive group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Add 119.16g (1.0mol) of N-methyldiethanolamine and 100g of acetone into the flask, and dropwise add 144.12g (2.0mol) of acrylic acid and 150g of acetone solution while stirring. The dropwise addition is completed within 0.5 hours, and the temperature rises to 45°C and react for 1 hour. The reaction system was lowered to room temperature, filtered and washed 3 times with acetone to obtain a white solid A with a yield of 87.6%. The structure of product A is shown as follows by infrared and hydrogen nuclear magnetic resonance analysis. The proton nuclear magnetic resonance spectrum of product A is as attached figure 1 shown. The carbon magnetic resonance spectrum of product A is attached figure 2 shown.

[0050]

[0051] Among them, attached drawing l 1 In the HNMR spectrum, the characteristic peak with a chemical shift of 3.16ppm is the proton peak at a; the characteristic peak with a chemical shift of 3.55-3.58ppm is the proton peak at b; the characteristic peak...

Embodiment 2

[0055] Add 156.2g (1mol) of N,N'-dimethylaminopropylacrylamide and 150g of acetonitrile into the flask, add 14.41g (0.2mol) of acrylic acid dropwise while stirring, and add dropwise within 0.5 hours After completion, the temperature was raised to 50° C., and the reaction was carried out for 120 hours. The reaction system was lowered to room temperature, filtered and washed 3 times with acetonitrile to obtain white solid B with a yield of 86.2%. The structure of the product B is shown as follows by infrared and hydrogen nuclear magnetic resonance analysis. The proton nuclear magnetic resonance spectrum of product B is as attached image 3 shown. The carbon magnetic resonance spectrum of product A is attached Figure 4 shown.

[0056]

[0057] Among them, attached image 3 1 In the HNMR spectrum, the characteristic peaks with a chemical shift of 5.75-6.28ppm are the proton peaks at a and b; the characteristic peaks with a chemical shift of 3.29-3.37ppm are the proton pe...

Embodiment 3

[0059] Add 89.14g (1.0mol) of N,N'-dimethylethanolamine and 100g of tetrahydrofuran into the flask, and add 64.05g (0.5mol) of 4-carbonyl-5-hexenoic acid and 70g of The tetrahydrofuran solution was added dropwise within 0.5 hours, and reacted at 0°C for 120 hours. The reaction system was cooled to room temperature, filtered and washed 3 times with chloroform to obtain white solid C with a yield of 90.1%. Through infrared and proton magnetic resonance analysis identical with embodiment 1, 2, the structure of determining product C easily is as follows:

[0060]

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PUM

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Abstract

The invention discloses a synthesis method for a betaine-type amphoteric ion compound containing a reactive group. The synthesis method comprises two synthesis methods, namely, a synthesis method for a betaine-type amphoteric ion compound containing carbon-carbon double bonds, and a synthesis method for a betaine-type amphoteric ion compound containing hydroxyl group, wherein the synthesis method for the betaine-type amphoteric ion compound containing carbon-carbon double bonds comprises the step of reacting tertiary amine containing carbon-carbon double bonds and having a molar ratio of 1: 0.2 to 1: 1.5 with a carboxylic acid compound or a sulfonic acid compound containing an alpha, beta-unsaturated ketone structure for 1-120 hours at 0-100 DEG C in a condition of the presence of a first solvent and a polymerization inhibitor; and the synthesis method for the betaine-type amphoteric ion compound containing hydroxyl group comprises the step of reacting tertiary amine containing hydroxyl group and having a molar ratio of 1:0.5 to 1:2 with a carboxylic acid compound or a sulfonic acid compound containing an alpha, beta-unsaturated ketone structure for 1-120 hours at 0-100 DEG C in a condition of the presence of a second solvent. The synthesis method is simple, moderate in conditions, few in side reactions, high in product purity, simple in purification process, and high in yield, thus being capable of reducing the synthesis cost for the product.

Description

technical field [0001] The invention relates to a betaine type zwitterionic compound, in particular to a synthesis method of a betaine type zwitterionic compound containing a carbon-carbon double bond or a hydroxyl group. Background technique [0002] In recent years, studies have shown that there is a strong electrostatic force between carboxybetaine and sulfonate betaine zwitterionic compounds and water molecules, which can make the surface have a stable water layer, so that carboxybetaine Or the surface of sulfobetaine group has excellent resistance to non-specific protein adsorption, bacteria, microbial adhesion and anticoagulant function. Therefore, it is widely used in biomedical materials, marine antifouling materials and other fields. [0003] At present, the synthesis of carboxylic betaines is mainly prepared by reacting tertiary amines with α-halogenated acids or sodium salts of α-halogenated acids. irritating. When α‐halogenated acid sodium salt is used as raw ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/12C07C229/16C07C229/22C07C227/08C07C309/15C07C303/32
Inventor 李光吉罗熙雯刘云鸿陈志锋王立莹林殷雷
Owner SOUTH CHINA UNIV OF TECH
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