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Preparation method of chitosan quaternary ammonium salt

A technology of chitosan quaternary ammonium salt and chitosan, which is applied in the field of polymer modification, can solve the problems of poor water solubility and low reactivity, achieve good selectivity and reduce energy consumption

Active Publication Date: 2016-11-30
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The existing published patents related to the preparation of quaternary ammonium salts by using dimethyl carbonate all use dimethyl carbonate to quaternize short-chain tertiary amines and ester amines, but existing documents and patents and other data all show that, but As a methylation reagent, dimethyl carbonate has low reactivity and usually requires the combined action of high temperature and pressure and a catalyst; at the same time, since chitosan is a natural polymer with poor water solubility, it is difficult to directly perform N-position quaternization

Method used

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  • Preparation method of chitosan quaternary ammonium salt
  • Preparation method of chitosan quaternary ammonium salt

Examples

Experimental program
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Effect test

Embodiment 1

[0030] 5 grams of chitosan, 20 grams of formaldehyde, 20 grams of formic acid and 90 grams of distilled water were added into a three-necked flask, the magnetic stirring speed was 500 r / min, and the mixture was condensed and refluxed at 70°C for 120 hours to obtain a light yellow solution. The resulting light yellow solution was distilled under reduced pressure at 0.05MPa and 65°C for 25min, adjusted to pH=13 with sodium hydroxide solution, suction filtered at 0.05-0.1MPa, washed with absolute ethanol until neutral, and then washed with 1mol / L of hydrochloric acid to adjust the pH to 4, wash the obtained white precipitate and freeze-dry it at -30°C to obtain N, N-dimethyl chitosan;

[0031] Take 10 grams of (1-butyl-3-methylimidazole) chloride, add it into a 50 mL three-necked flask, turn on the magnetic stirrer and condensed water, and set the speed at 500 r / min. After the temperature reached 100°C, 0.5 g of N, N-dimethyl chitosan was added three times, and after stirring an...

Embodiment 2

[0034] N, the preparation method of N-dimethyl chitosan is with example 1;

[0035] Take 5 grams of 1-ethyl-3-methylimidazole acetate, add it into a 50 mL three-necked flask, turn on the magnetic stirrer and condensed water, and set the speed at 600 r / min. After the temperature reached 90°C, 0.5 g of N, N-dimethyl chitosan was added three times, and after 2 hours of reaction, a uniform and viscous N, N-dimethyl chitosan mixture was obtained; Dimethyl carbonate (10 times excess) was added to the mixture, reacted at 130°C under reflux for 2.5 hours, the resulting solution was washed 5 times with absolute ethanol, and dried in an oven at 110°C, the obtained solid passed 1 H NMR and 13 C NMR analysis shows that the product is a chitosan quaternary ammonium salt with a quaternary ammonium degree of 8.78%.

Embodiment 3

[0037]N, the preparation method of N-dimethyl chitosan is with example 1;

[0038] Take 15 grams of 1-allyl-3-methylimidazole chloride and add it into a 50 mL three-necked flask, turn on the magnetic stirrer and condensed water, and set the speed at 400 r / min. After the temperature reached 110°C, 0.5 g of N, N-dimethyl chitosan was added three times, and after 2 hours of reaction, a uniform and viscous N, N-dimethyl chitosan mixture was obtained; 2.5 g Dimethyl carbonate (5 times excess) was added to the mixture, reacted under reflux at 170°C for 3 hours, the resulting solution was washed 6 times with absolute ethanol, and dried in an oven at 120°C, the obtained solid was N, N , N-trimethyl chitosan.

[0039] pass 1 H NMR and 13 C NMR analysis shows that the quaternary ammonium degree of the product chitosan quaternary ammonium salt is 12.39%.

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Abstract

The invention relates to a preparation method of a chitosan quaternary ammonium salt, and belongs to the technical field of high molecule modification. The preparation method comprises following steps: firstly, chitosan is subjected to Eschweiler-Clarke reaction so as to obtain N, N-dimethyl chitosan; at an ionic liquid environment, quaternization reagent dimethyl carbonate is added for quaternization of N, N-dimethyl chitosan; and at last, an obtained reaction product solution is washed with an organic solvent and is dried so as to obtain N, N, N-trimethyl chitosan. According to the preparation method, the quaternization reagent dimethyl carbonate is nontoxic, the reaction products are carbon dioxide and methyl alcohol, and methyl alcohol can be recycled to prepare dimethyl carbonate, so that the preparation method is green, and is friendly to the environment. In addition, compared with dimethyl sulfate, selectivity of methylation reaction of dimethyl carbonate with amines is higher.

Description

technical field [0001] The invention relates to a preparation method of chitosan quaternary ammonium salt, belonging to the technical field of polymer modification. Background technique [0002] Chitosan, also known as deacetylated chitin, is obtained from chitin through deacetylation. Because chitosan can form a large number of hydrogen bonds in the molecule and between molecules, coupled with the regularity of the structure, the molecule is easy to crystallize and has poor solubility. application. N, N, N-trimethyl chitosan (TMC) is the product of chitosan C2-amino alkylation, the positive charge of chitosan after quaternization modification increases, and in a larger pH range Both have good water solubility. The products are widely used in the fields of drug synthesis, drug carrier, bacteriostat, food preservation and so on. [0003] Since the first report of chitosan and methyl iodide to prepare N, N, N-trimethyl chitosan technology in 1985, researchers began to turn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
CPCC08B37/003
Inventor 龙柱吴美燕张丹王长红
Owner JIANGNAN UNIV
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