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Chitosan-alkoxy formamide and preparation method thereof

A technology of alkoxy formamide and chitosan, which is applied in the field of chitosan-alkoxy formamide and its preparation, can solve the problems of irregular and different structures, and achieve high structural regularity, chemical characteristics or physical properties. Good effect

Inactive Publication Date: 2015-12-16
WUHAN INSTITUTE OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the chitosan derivatives they synthesized all use chitosan with some residual acetyl groups as raw materials, and all of them are partially N-acylated chitosan derivatives, so their structures are not regular enough. It may be greatly restricted, such as these chitosan derivatives are not suitable for the preparation of chiral separation materials [(9).OkamotoY.etal.JournalofChromatographyA,2003,1021,83–91]. Sugar-alkoxy formamide (such as chitosan-methoxy formamide, etc.) may show different biological activities from chitosan derivatives with irregular structure, so it is necessary to develop chitosan with regular structure- Alkyloxyformamide, establishing its synthetic method

Method used

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  • Chitosan-alkoxy formamide and preparation method thereof
  • Chitosan-alkoxy formamide and preparation method thereof
  • Chitosan-alkoxy formamide and preparation method thereof

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preparation example Construction

[0032] Preparation of chitosan:

[0033] Pulverize the purchased flake chitin (shrimp shell) with a pulverizer, sieve (355 μm), collect the chitin under the sieve as raw material, and use two methods to deacetylate chitin (refer to literature 10-12);

[0034] The embodiment of the present invention adopts gel chromatography to measure the number average molecular weight (M) of chitosan n), when measuring the molecular weight of chitosan, the acetic acid (0.3M)-ammonium acetate (0.1M) buffer solution was used as the mobile phase, and polyethylene glycol was used as the standard.

[0035] Both chitosan and N-acylated chitosan can adsorb water molecules, so the existence of adsorbed water molecules should be considered when calculating element values.

Embodiment 1

[0037] Synthesis of chitosan-ethoxy formamide

[0038] 1) Add 1.50g (9.32mmol repeating unit) chitosan (100,000 number average molecular weight, 100% deacetylation degree) into a 250mL three-necked flask, add 20.00g of prepared 1.2wt% dilute hydrochloric acid solution, stir Dissolve chitosan until clear and transparent. Then weigh 25.00 g of methanol, add about 20.00 g of methanol into the three-necked flask, mechanically stir it evenly, and place the three-necked flask in an ice-water bath (temperature about 4° C.). After the temperature in the solution dropped and stabilized, 2.01 g (18.64 mmol) of ethyl chloroformate was quickly added. After reacting at 4°C for about 15 minutes, weigh 1.88g (18.64mmol) of triethylamine (the molar ratio of triethylamine to ethyl chloroformate is 1:1) and mix it with the remaining methanol, and add an appropriate amount of triethylamine Adjust the pH of the reaction solution to about 6, and intermittently add triethylamine during the reacti...

Embodiment 2

[0041] Synthesis of Chitosan-n-Pentoxyformamide

[0042] 1) 1.40g (8.69mmol repeating unit) chitosan (350,000 number average molecular weight, 98% degree of deacetylation) was added to a 250mL three-necked flask, and 36.95g of prepared 0.87wt% dilute hydrochloric acid solution was added, stirred Dissolve chitosan until clear and transparent. Then weigh 36.08g of methanol, add about 90% methanol into the three-necked flask, mechanically stir the three-necked flask to an ice-water bath (temperature about 6° C.). After the temperature in the solution dropped and stabilized, 10.18 g (69.52 mmol) of n-pentyl chloroformate was quickly added. Stir for 30min and mix well, remove the ice-water bath to allow the reaction to proceed at 26-27°C, weigh 7.02g (69.52mmol) of triethylamine (the molar ratio of triethylamine to n-pentyl chloroformate is 1:1) and Mix the remaining methanol, add an appropriate amount of triethylamine to adjust the pH of the reaction solution to about 6, and add...

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Abstract

The invention relates to a chitosan-alkoxy formamide and a preparation method thereof. The preparation method comprises the following steps: 1) dissolving chitosan with the deacetylation degree of 98% or above in a dilute hydrochloric acid water solution, adding excessive chloroformate and a right amount of methanol into the obtained solution, regulating the pH value of the reaction system by using tertiary amine as an acid-binding agent, and reacting to obtain partially N-acylated chitosan; and 2) dissolving the partially N-acylated chitosan in a lithium chloride N,N-dimethylacetamide solution, adding excessive chloroformate and a proper amount of methanol, regulating the pH value of the reaction system by using tertiary amine as an acid-binding agent, and reacting to generate the completely N-acylated chitosan-alkoxy formamide. The prepared material has the advantages of high structural regularity and favorable chemical or physical characteristics; and the prepared chitosan-alkoxy formamide has regular structure, and can be used as a raw material for synthesizing materials with requirements for high regularity, such as chiral parting materials and the like.

Description

technical field [0001] The invention relates to derivatives of natural polymer chitosan and a preparation method thereof, in particular to chitosan-alkoxy formamide and a preparation method thereof. Background technique [0002] with RR 1 NCOOR 2 The biological activity of structural carbamates has long attracted people's attention. It was found that it originated from physostigmine in physostigmine, and the main active structure was carbamate. After further research, it was found that this type of compound is a good insecticide [(1). . Development of carbamate insecticides. Pesticide Translation Collection. 1992, 14(5): 37-50]. Carbamate insecticides have the following characteristics: 1. Strong selectivity: this type of pesticide has special effects on chewing pests, such as pink bollworm, which is beyond the reach of many organophosphorus insecticides; 2. Broad spectrum; 3. Low toxicity to humans, animals and fish. Although the parent compounds of carbamate insecticid...

Claims

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Application Information

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IPC IPC(8): C08B37/08
Inventor 柏正武冯子维陈伟
Owner WUHAN INSTITUTE OF TECHNOLOGY
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