Method for preparing 6-amino-6-deoxycellulose

A technology of deoxygenated cellulose and cellulose solution, which is applied in the field of natural polymers and their chemical modification, can solve the problems of unfavorable derivatization and application, product insoluble in acidic aqueous solution, removal, etc., and achieve good application prospects and high yield , good reproducibility

Active Publication Date: 2019-10-15
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The 6-amino-6-deoxycellulose synthesized by this method also contains a certain amount of triphenylphosphine and triphenylphosphine oxide, which cannot be completely removed by purification methods such as washing and extraction, and the resulting product is insoluble In acidic aqueous solution, it is not conducive to further derivatization and application

Method used

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  • Method for preparing 6-amino-6-deoxycellulose
  • Method for preparing 6-amino-6-deoxycellulose
  • Method for preparing 6-amino-6-deoxycellulose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of 6-bromo-6-deoxycellulose: adding triphenylphosphine and NBS at 0 °C

[0043] Weigh 4g of dry cellulose into a 500mL three-neck flask, add 220mL of dry DMAc, heat to 130°C, and stir at this temperature for 2 hours. The mixture was cooled to 100° C., 56.5 g of lithium bromide was added, and stirred until the mixture became clear to obtain a cellulose solution. Add 180 mL of dry DMAc and stir at 100°C for 30 minutes. After cooling the cellulose solution with an ice-water bath to 0°C, add a solution of 16.2g of triphenylphosphine dissolved in 40mL of DMAc, stir, and dropwise add a solution of 11.0g of NBS dissolved in 30mL of DMAc, and finish dropping within 30min. The temperature of the reaction liquid was raised to 70° C., and the reaction was stirred for 2 hours. After the reaction was completed, the reaction solution was added dropwise to 1200 mL of distilled water, stirred overnight, filtered, washed with acetone until the filtrate had no UV absorption...

Embodiment 2

[0045] Preparation of 6-bromo-6-deoxycellulose: adding triphenylphosphine and NBS at 5 °C

[0046] The temperature of the reaction solution was adjusted to 5°C, and triphenylphosphine and NBS were added at this temperature, and the rest of the method was the same as in Example 1 to prepare 6-bromo-6-deoxycellulose. The productive rate is 97%, and the infrared spectrogram is as attached figure 1 As shown in B, IR(KBr,cm -1 )υ: 3464(-OH), 2899(-C-H), 1726(-O-C=O), 664(-C-Br). in the attached figure 1 1726cm on B -1 Nearby ester group peak and 1637cm -1 Compared with the cellulose skeleton peak of A, it is weaker, and there is no obvious difference with the peak intensity in A spectrum.

Embodiment 3

[0048] Preparation of 6-azido-6-deoxycellulose: The ratio of reaction solvent DMSO to 6-bromo-6-deoxycellulose is 40mL / g

[0049] The ratio of the reaction solvent DMSO and 6-bromo-6-deoxycellulose was adjusted to 40mL / g, and the rest of the method was the same as that in comparative experiment 1 to prepare 6-azido-6-deoxycellulose. The productive rate is 78%, and the infrared spectrogram is as attached figure 2 Shown: IR(KBr,cm -1 )υ: 3433(-OH), 2890(-C-H), 2110(-N3 ), at 2110cm -1 There is a strong azide absorption peak, indicating that 6-azido-6-deoxycellulose is generated.

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Abstract

The invention relates to a method for synthesizing 6-amino-6-deoxycellulose. The method comprises the following steps: 1) dissolving cellulose into an N,N-dimethylacetamide solution of lithium bromide, sequentially dropping triphenylphosphine and a DMAc solution of bromo-succinimide into the cellulose solution, and performing stirring for a reaction to obtain 6-bromo-6-deoxycellulose; 2) dissolving the 6-bromo-6-deoxycellulose obtained in the step 1) into a dimethylsulfoxide solution, adding excessive sodium azide, and carrying out a reaction to obtain 6-azido-6-deoxycellulose; 3) dissolving the 6-azido-6-deoxycellulose obtained in the step 2) into the dimethylsulfoxide solution, adding excessive sodium borohydride, and carrying out a reaction, thereby obtaining the 6-amino-6-deoxycellulose. According to the method disclosed by the invention, the azido can be completely reduced as amino with the sodium borohydride, the 6-amino-6-deoxycellulose with high purity and high substitution degree can be prepared, the adopted process is simple in operation and efficient, and the needed raw materials are readily available.

Description

technical field [0001] The invention relates to a natural polymer and a chemical modification method thereof, in particular to a preparation method of 6-amino-6-deoxycellulose. [0002] technical background [0003] Amino polysaccharides are an important class of sugar compounds, the amino groups in the structure endow them with many unique physiological, pharmacological functions and chemical properties. Chitosan is an aminopolysaccharide widely found in nature. The presence of the amino group at the C-2 position endows chitosan with more physiological activity and reactivity. For example, in terms of chiral recognition, the amino group and hydroxyl group are modified separately The obtained chitosan derivative not only has good organic solvent tolerance, but also has good enantiomeric separation performance. Cellulose is a natural polysaccharide that exists more widely in nature. Amino deoxycellulose has a similar structure to chitosan and has important application value. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B15/06
CPCC08B15/06
Inventor 柏正武蔡明兰
Owner WUHAN INSTITUTE OF TECHNOLOGY
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