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N-glucose hydrochloride-based maleamic acid monomer, and preparation method and application thereof

A technology of glucosamine hydrochloride and maleamic acid is applied in the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., and can solve the problems of strict reaction temperature and device requirements, poor water solubility, and complicated steps. , to achieve the effect of simple and safe reaction conditions, convenient operation and high yield

Active Publication Date: 2017-10-24
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Maleamic acid compounds are generally synthesized by acylation of maleic anhydride and compounds with amino groups. However, the synthetic maleamic acid types researched and produced at the present stage are less, and their water solubility is poor. Strict requirements on equipment and equipment, complex steps, cannot meet the needs of easy preparation of many water-soluble treatment agents

Method used

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  • N-glucose hydrochloride-based maleamic acid monomer, and preparation method and application thereof
  • N-glucose hydrochloride-based maleamic acid monomer, and preparation method and application thereof
  • N-glucose hydrochloride-based maleamic acid monomer, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 1.4mol maleic anhydride to a dry three-necked round-bottomed flask, take 40mL glacial acetic acid to dissolve, and slowly drop the remaining 40mL glacial acetic acid solution in which 1.0mol glucosamine hydrochloride is dissolved, and stir at 25°C for 3 hours , after a white powder is formed, suction filtration-washing-suction filtration, and drying to obtain N-glucose hydrochloride maleamic acid, the yield is 77% by weight calculation. Its infrared absorption spectrum is as figure 1 As shown, the H NMR spectrum is shown as Figure 4 shown. The product had a melting point of 171°C.

Embodiment 2

[0035] Add 1.0mol maleic anhydride to a dry three-necked round-bottomed flask, take 20mL glacial acetic acid to dissolve, and slowly drop the remaining 20mL glacial acetic acid solution in which 1.0mol glucosamine hydrochloride is dissolved, and stir at 50°C for 2 hours , after a white powder is formed, suction filtration-washing-suction filtration, and drying to obtain N-glucose hydrochloride maleamic acid, the yield is 52% by weight calculation. The product had a melting point of 169°C.

Embodiment 3

[0037] Add 1.2mol of maleic anhydride to a dry three-neck round-bottom flask, take 60mL of glacial acetic acid and dissolve it, and slowly add the remaining 60mL of glacial acetic acid solution in which 1.0mol of glucosamine hydrochloride is dissolved, and stir at 30°C for 6 hours , after a white powder is formed, suction filtration-washing-suction filtration, and drying to obtain N-glucose hydrochloride maleamic acid, the yield is 70% by weight calculation. The product had a melting point of 171°C.

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Abstract

The invention discloses an N-glucose hydrochloride-based maleamic acid monomer, and a preparation method and application thereof. The structure of the monomer is as follows: the formula is as shown in the description. The preparation method comprises the following steps: dissolving C mol of glucosamine hydrochloride into B mL of solvent; and dropwise adding A mol of maleic anhydride and B mL of solvent mixed solution while stirring until white powder is generated and white powder is not increased any more. The N-glucose hydrochloride-based maleamic acid synthesized by the method serves as a brand new amido acid compound, can serve as an intermediate of an imide chemical product and also can directly serve as a raw material of aqueous phase reaction or a functional monomer; furthermore, the reaction condition is simple, convenient and safe, operation is benefited, and the yield is high.

Description

technical field [0001] The invention relates to the field of synthesis of maleamic acid compounds, and furthermore, relates to an N-glucose hydrochloride-based maleamic acid monomer, a preparation method and an application thereof. Background technique [0002] Maleamic acid compounds are an important class of organic compounds. Maleimide compounds prepared from such organic compounds as intermediates through catalytic ring closure reactions have been extensively studied in biochemistry, organic chemistry and polymer chemistry. And maleamic acid itself, because of its asymmetric carbon atom, amide structure, carboxylic acid group and a variety of designable N-substituent groups, can also be designed as a functional monomer through molecular design, and can be self-polymerized or copolymerized. Preparation of high-performance water-soluble polymers. [0003] Maleamic acid compounds are generally synthesized by acylation of maleic anhydride and compounds with amino groups. Ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/06C07H1/00C08F220/56C08F220/58C08F222/02C09K8/035
CPCC07H1/00C07H13/06C08F220/56C08F220/58C08F220/585C09K8/035C08F222/02
Inventor 何剑杨小华林永学王琳董晓强杨帆李舟军王海波
Owner CHINA PETROLEUM & CHEM CORP
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